Thought catalog questions

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120+ Deep Conversation Starters to Spark a Meaningful Discussion [2020]

These deep questions are the perfect questions to get to know someone. If you meet someone you feel an immediate connection with, ask them these deep questions to get to know them on an intimate level as quickly as possible.

Questions To Ask If You Want To Get To Know Someone On A Deeper Level

1. What’s your philosophy in life?

2. What’s the one thing you would like to change about yourself?

3. Are you religious or spiritual?

4. Do you consider yourself an introvert or an extrovert?

5. Which parent are you closer to and why?

6. What was the best phase in your life?

7. What was the worst phase in your life?

8. Is what you’re doing now what you always wanted to do growing up?

9. What makes you feel accomplished?

10. What’s your favorite book/movie of all time and why did it speak to you so much?

11. What is a relationship deal breaker for you?

12. Are you more into looks or brains?

13. Would you ever take back someone who cheated?

14. How do you feel about sharing your password with your partner?

15. When do you think a person is ready for marriage?

16. What kind of parent do you think you will be?

17. What would you do if your parents didn’t like your partner?

18. Who is that one person you can talk to about just anything?

19. Do you usually stay friends with your exes?

20. Have you ever lost someone close to you?

21. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

22. What’s an ideal weekend for you?

23. What do you think of best friends of the opposite sex?

24. Do you judge a book by its cover?

25. Are you confrontational?

26. When was the last time you broke someone’s heart?

27. Would you relocate for love?

28. Did you ever write a journal?

29. What are you most thankful for?

30. Do you believe in second chances?

31. What’s the one thing that people always misunderstand about you?

32. What is your idea of a perfect vacation?

33. What did your past relationship teach you?

34. What are your thoughts on online dating or tinder?

35. What’s on your bucket list this year?

36. When have you felt your biggest adrenaline rush?

37. What is the craziest thing you’ve ever done and would you do it again?

38. If a genie granted you 3 wishes right now, what would you wish for?

39. What’s your biggest regret in life?

40. What do you think about when you’re by yourself?

Get To Know Someone
The remaining bonus questions were written by a collective author, and not Rania Naim

Questions To Ask Someone If You’re Just Starting To Get To Know Who They Really Are

41. Does your job make you happy?

42. What did you want to be when you were younger?

43. Why did your last relationship end?

45. What’s been your biggest mistake so far in life and what did you learn from it?

46. Where is your favorite place in the entire world to go?

47. What are your top five favorite movies?

48. What are some of your favorite songs?

49. What qualities do you admire about your parents?

50. How would you describe your best friend?

51. What’s your favorite hobby to do alone?

52. What’s something you can’t go a day without doing?

53. What’s the most spontaneous thing you’ve done lately?

54. What’s the craziest thing you’ve ever done for love?

55. What’s your biggest pet peeve?

56. Why do you think you’re still single?

57. What accomplishment are you most proud of?

58. What is one dream you have yet to accomplish?

59. What is your greatest fear?

60. What are three things you value most about a person?

61. Who are five people you are closest with?

62. What is the greatest struggle you’ve overcome?

63. If you could live anywhere in the world where would it be?

64. What’s the most exciting thing that’s happened this past year?

65. What’s your favorite beer?

66. What’s one thing that bothers you most about the world today?

67. Who are you closer with your mom or your dad?

68. If you could change one thing about yourself what would it be?

69. If you could change one thing about the world what would it be?

70. Who was your favorite teacher and why?

71. What sport did you fall in love with?

72. What is the weirdest thing about you?

73. What was your longest relationship?

74. What would your best friend say is your best quality?

75. Who is your favorite historical figure?

76. What made you choose the college you went to?

77. If you could tell your former self one thing right now what would it be?

78. What food could you not live without?

79. Dogs or Cats?

80. What’s closest you’ve ever come to being arrested?

81. What was your best birthday?

82. What’s one thing you wish you knew how to do?

83. Where’s one place you’d like to go that you haven’t been?

84. What was the last book you read? And When?

85. Where do you usually get your news?

86. What are some of your own personal goals in the next 5 years?

87. What would you consider your greatest accomplishment so far?

88. If you could get away with anything that you do?

89. Who is your greatest hero?

90. What’s the greatest risk you’ve ever taken?

Questions To Ask Someone If You Want Them To Bare Their Soul

91. Why are we here?

92. If heaven is real and you died tomorrow, would you get in?

93. Do you believe in fate?

94. How do you think people see you?

95. If you had the ability to erase something that you did in the past, what
would it be?

96. What song makes you unconditionally happy?

97. If you could have anybody else’s life, who’s would you take?

98. What fictional character do you most relate to?

99. If I asked you at age 5 what you wanted to be when you grew up, what would you say?

100. What is your biggest irrational fear?

101. If you could take us anywhere in the world right now, where would you take us?

102. What is your biggest regret?

103. If you died tomorrow, what would you wish you had done?

104. Can you pin point the moment in your life where you were the happiest?

105. What song makes you unconditionally sad?

106. If past lives are real, what was yours?

107. Have you ever seen something you can’t explain?

108. What is your biggest accomplishment?

109. If you could do one thing without suffering the consequences, what would
you do?

110. What is the strangest dream you’ve ever had?

Questions To Ask If You’re Ready To Know Dig Even Deeper

111. What is the darkest thought you’ve ever had? What about the darkest thing you’ve never told anybody?

112. Is there something out there, a thought, an idea, a current event, or a fear that you find deeply unsettling?

113. What would you consider to be your deepest fear? (This question can be really telling of the depth or lack thereof of a person.)

114. Is there an activity that calms you? A place or a thing that makes you feel at ease?

115. What makes you feel uneasy? Overwhelmed? Anxious?

116. What is your favorite song and why?

117. Do you have a favorite book? A line in a piece of literature? A poem? Why do you relate to it?

118. What scene in a movie has evoked the most feelings out of you?

119. What do you do or where do you go when you need to be alone?

120. What makes you feel like you need to be alone?

121. Can you remember a time in your life you felt the most alive? Tell me everything about that memory.

122. When have you felt the lowest in your life?

123. Where have you felt the most failure? The most success?

124. Tell me about the facts or harsh truths you choose to ignore but know you shouldn’t.

125. When have you felt like you were living life to the fullest? When have you felt like you weren’t?

126. What is the first lie you ever told? Which is the biggest?

127. What is the first secret you ever kept from anybody? Which is the biggest?

128. Are you a religious or spiritual person? Tell me why and tell me how.

129. Have you always had the same political beliefs? Is there something that impacted them?

130. Where do you find meaning in your life?

131. Have you ever been in love? Tell me about the times you have been.

132. Tell me about the times someone broke your heart.

133. Why did you cry the last time you did so?

134. Have you ever cried tears of joy?

135. What did you do when you hurt someone the most?

136. If your life was a movie or a book what would be the title to it?

137. When have you caused the most harm to yourself?

138. What has been the biggest change you ever made that made you the most proud of yourself?

139. Think about the people you love the most in your life, what do you do for them?

140. Is home for you a place or a feeling? Describe that place or describe that feeling.

141. If you could be anywhere other than where you are right now, where would you be and what would you be looking at?

142. Have you ever questioned your sanity and why?

143. What is your most cherished childhood memory?

144. Have you ever had dreams about a past life?

145. Do you have any recurring dreams or nightmares?

146. Do you believe more in fate or that we are the creators of our own destinies because we are governed by free will?

147. Do you believe in extraterrestrial life? Elaborate on why or why not.

148. Would you find more comfort in the theoretical idea that that we were the most advanced species in outer space or would you find more comfort in the idea that we weren’t?

149. What would be your thought process if you were presented with irrefutable evidence that a god didn’t exist? What would be your thought process if you were presented with irrefutable evidence that a god
did exist?

150. What do you think was there before the universe came into creation?

151. Do you believe in other dimensions and parallel universes?

152. How do you define art?

153. If you could have the option of eradicating pain from your life would you choose to do so? Why or why not?

154. Is a life exclusive to pleasure (no suffering) worthwhile?

155. What do you think happens after death, if anything?

156. If you could be given the date of your death would you want to know it?

157. Presented with the opportunity to be immortal would you take it?

158. Would you rather be loved or love?

159. How do you define beauty?

160. Where does happiness come from? Define what happiness means to you.

161. Do you believe yourself to be truly free? If so, why? If not, what is holding you back?

162. Deja-vu: is there anything to it or merely coincidence?

Unconventional Questions That Will Help You Get To Know Someone

163. What was your father or mother like at home? How does he or she act different outside of family?

164. If you were given a choice to choose your manner of death, how would you die?

165. Tell me a really, really stupid joke that made you laugh.

166. Pick two out of physical chemistry, lifestyle compatibility, emotional compatibility and intellectual compatibility.

167. If you were forced to vote for one the biggest dictators of history, (Hitler, Mussolini, Mugabe, Mao, Saddam or Stalin), which one would you pick and why?

168. Show me a music track or a scene from a film that made you tear up.

169. If you could have any animal in the world as a pet, what would it be and why?

170. If you were given a chance to explore the oceans, go to outer space or visit 50 different countries, which one you choose and why?

171. Do you think that men are more rational and women are more emotional?

172. Out of the negative emotions of greed, anger, jealousy and hate, which one would you say affects you the most?

173. Out of the positive emotions of compassion, positivity, enthusiasm and initiative, which one is your biggest strength?

174. If you could be President of your country for an hour, what is the one thing that you would change?

175. Describe your best first kiss.

176. Has another’s pain ever given you joy? Be totally honest.

177. Tell me your biggest strength outside of your workplace.

178. If you were given a choice to turn into a zombie or to die, which would you pick?

179. If you had to pick one, what is the most important value you would teach your children? Honesty, Kindness or Courage?

180. Are you health conscious?

181. Name the one bad quality you wouldn’t mind in a partner.

182. Name the one worst quality you cannot tolerate in a partner.

183. Tell me your biggest supernatural or paranormal fear?

184. If you got a free cheque for $5,000 right this second, how would you use it?

185. Name one really surprising thing that set your heart pumping and gave you an adrenaline rush.

186. Tell me about the time you were so embarrassed in love, you wished you could disappear right there and then.

187. Have you ever been unable to sleep? What do you do with your time then?

188. Tell me about your biggest love regret that made you wish you could turn back time?

189. Do you believe in materialism or spirituality?

190. If you were forced to pick one religion on this planet, which one would it be and why?

191. What is the most romantic and loving thing you have ever done for somebody?

192. What is the most adventurous thing you have ever done in your life?

193. What’s your day-to-day mantra?

194. What quote resonates with you more than any other?

195. What’s your anti-motto?

196. What trait do you envy in others?

197. What skill do you wish you had?

198. How do you wish to be remembered?

199. How would your best friend describe you in five words?

200. How would you summarize your life purpose? Thought Catalog Logo Mark


If You’re Not Doing These Five Things Every Day, You’re Sabotaging Your Relationship

In order to have a healthy relationship with a person, you have to be brave enough to ask those uncomfortable, serious questions when the time comes. Having those deeper conversations about your hopes, dreams, and fears can be really hard but also really helpful in developing a successful, romantic relationship. Not only is it a good way to start a great conversation, but also a good way to really understand each other and see if you’re compatible in love or if you have the same outlook on life.

FunQuestions For Couples To Ask Each Other 

Are you just starting a new relationship? Here are some random and funny questions you can ask each other to simply get the conversation going. 

  1. What is the weirdest thing you are afraid of? 
  2. What is something that makes you laugh? 
  3. Have you ever lied to get out of a conversation? 
  4. Would you rather live somewhere that is warm, hot, cold, or gets a mix of all the seasons? 
  5. Would you rather be unable to lie or be unable to speak? 
  6. Is there a song that makes you think of me? 
  7. Do you like to read? If so, what is your favorite book? 
  8. What is your favorite drink (alcoholic or non-alcoholic)?
  9. What qualities do you look for in a partner? 
  10. When was your first kiss? 
  11. What is your favorite sport to watch? 
  12. What is something you love to do in your free time? 
  13. What is the worst thing that has happened to you on a date? 
  14. Do you snore? 
  15. What is your favorite flavor of ice cream? 
  16. Do you hold grudges or do you forgive easily?
  17. What kind of music do you like listening to? 
  18. Are you an early riser or a night owl? 
  19. When you were a kid, what was your dream job?  
  20. What is your spirit animal?
  21. What is your favorite color?
  22. What was the most embarrassing moment in your life? 
  23. What is your favorite movie?
  24. Do you prefer Halloween or Christmas? 
  25. Have you ever been heartbroken? 
  26. What is your favorite way to watch a movie: in theaters, in bed, or on the couch?
  27. What is a bad habit you have? 
  28. Have you ever dyed or wanted to dye your hair?
  29. Where is your dream vacation destination? 
  30. How do you feel about large crowds of people? 
  31. If you could trade lives with someone, who would it be? 
  32. What is your favorite food?
  33. What is one thing no one knows about you? 
  34. Do you use social media? 
  35. If you had a bad day, how would you want to spend your night to make it end on a good note? 
  36. If you were a superhero, what would your superpower be? 
  37. Did you like high school or college better? 
  38. What exotic animal are you interested in? 
  39. Have you ever gone to therapy? 
  40. Which of your friends are the most like you? 
  41. If you had one week left on earth, what would you do? 
  42. What is a quality you really like about yourself? 
  43. If a genie gave you three wishes, what would you ask for? 
  44. Do you like coffee? If so, how do you take it? 
  45. Are you more of an optimist, a pessimist, or a realist? 
  46. Do you like to play video games? 
  47. If you could move anywhere in the world and not have to work for a whole year, where would you go? 
  48. Do you have a go-to karaoke song? 
  49. Do you believe in aliens?
  50. Do you believe in ghosts?
  51. If you could visit any major city, which one would you go to?
  52. What is your favorite meal of the day: breakfast, lunch, or dinner?
  53. Are you superstitious? 
  54. You’re at brunch…do you order a mimosa or a bloody mary? 
  55. Do you like physical activities, like hiking, skiing, skateboarding, doing yoga?
  56. Who is the first person you call when you’re in trouble? 
  57. Are you friends with any of your exes? 
  58. What is your ideal Sunday morning?
  59. Which one do you prefer: the beach, the mountains, the desert, or the city?
  60. Are there any conspiracy theories that fascinate you?

Questions For Couples To Get Deeper 

Developing emotional intimacy with your partner is truly the most important thing in a relationship. Without intimacy or closeness, both emotionally and physically, the relationship is almost doomed. Before you two say “I do”, there are some deep questions you should ask each other to get a little deeper in love.

  1. What is your ideal first date? 
  2. What is your zodiac sign? 
  3. What is something you wish someone taught you a long time ago? 
  4. Can you tell me a secret? 
  5. What is your biggest fear? 
  6. What is your favorite thing about me?
  7. What is your love language?
  8. What is your Myers Briggs type? 
  9. Do you believe in fate? 
  10. What did your last relationship teach you? 
  11. What is something you miss about being a kid? 
  12. What, to you, is more important: traveling or owning luxurious items?
  13. What are 3 things on your bucket list? 
  14. What is your biggest goal in life?
  15. Who is your role model? 
  16. Who do you miss the most? 
  17. What was your first thought when we met? 
  18. Would you rather be crazy rich or deeply in love? 
  19. What makes you happy? 
  20. Do you believe in soulmates or love at first sight? 
  21. If you could plan a perfect date for us, what would we do? 
  22. When was the last time you cried? 
  23. Have you ever been in love? 
  24. Would you rather be rich and miserable or poor and happy? 
  25. Do you have any relationship deal-breakers? 
  26. What are the five things you are most thankful for right now? 
  27. What about yourself are you the proudest of? 
  28. Do you ever want to get married?
  29. What is something that calms you down? 
  30. Would you say you’re a confident person?
  31. Have you ever done hard drugs? If so, what? 
  32. Are you typically a leader or a follower? 
  33. What is the hardest life lesson you’ve had to learn? 
  34. What do you think your weaknesses are? 
  35. What is your biggest regret in life? 

Questions For Couples To Ask Before Marriage 

No matter if you’re going to be a husband or a wife or you’re a boyfriend or a girlfriend–if you’re in a committed relationship with someone, consider asking these serious questions. You can either keep the answer to yourself or think about actually bringing them up as a conversation starter to see what your spouse or partner has to say. Having a deep conversation with your partner every once in a while is great for building trust and making sure you’re on the same page about the relationship. 

If you’re feeling stuck and don’t really know where to start this kind of conversation, here are some insightful questions you can start with:

  1. Do you like pets? If so, what kind of pet would you want? 
  2. Have you ever cheated on someone while in a relationship? 
  3. Are you religious or spiritual?
  4. What are your political views?
  5. How do you feel about abortion?
  6. Do you want kids? If so, how many?
  7. Would you ever consider adoption? 
  8. What should we do if a family member wants to borrow a large sum of money? 
  9. What, do you think, is the key to a successful relationship? 
  10. What relationship goals do you have for us? 
  11. Do you deal with any mental health issues I should be aware of? If so, when something arises, how can I help? 
  12. If you could describe our relationship in one word, what would it be?
  13. Does anyone in your family suffer from alcoholism or drug addiction?
  14. What is your family’s medical history like? 
  15. What is your biggest fear about marriage?
  16. If we get stuck in our marriage, would you be willing to seek outside help with a therapist? 
  17. What excites you about getting married?
  18. What do you think our life will look like in 10 years? 
  19. Do you think we’re comfortable enough with each other to discuss our needs in the bedroom? 
  20. Do you have any doubts about our relationship? 
  21. If, for medical reasons, we can’t have sex, how drastically will our relationship change? 
  22. How often would you want to visit your family or my family? 
  23. What role does your family play in our life together? 
  24. Would you ever relocate for love? 
  25. How do you handle your anger?
  26. Is alone time important to you? 
  27. Would you say you are a giver or a taker or a matcher? 
  28. Is there something about your past that I should know about? 
  29. Have you ever been to prison?
  30. When we retire, where do you want to live? 
  31. Do you have any love or relationship questions you want to ask me? 

Questions For Couples That Lead To Love

To Fall in Love With Anyone, Do This was an essay written by Mandy Len Catron where she referenced a psychologist’s study on love and whether or not intimacy can be deepened based on asking each other 36 questions. 

The idea of the study is that you let yourself open up and be vulnerable with a person by answering a question or two that you wouldn’t normally be asked (even though they are topics we’ve all thought about from time to time but have never said anything about). The series jumps from a random question to a fun question to a personal, deep question and so on. You can find the full list of questions here, but here are some to get you thinking:  

  1. What would be considered a “perfect” day? 
  2. Given the choice of anyone in the world, whom would you want to have as a dinner guest? 
  3. What roles do love and affection play in your life? 
  4. Do you have a secret hunch about how you will die? 
  5. Tell your partner what you like about them. 
  6. What is the great accomplishment of your life? 
  7. What do you value most in a friendship? 
  8. What is your favorite memory? 
  9. Is there something you’ve dreamed of doing for a long time but you’ve never done it? If so, what is it and why haven’t you done it? 
  10. Let’s say your house catches fire. Your loved one(s) and your pets are safe already. What is one thing you would save? 

Intimate Questions For Couples For Rekindling The Spark

Looking to spice things up in the bedroom? Here are some romantic questions to ask each other and see if you’re on the same page about love and intimacy in your relationship. 

  1. What is your biggest fantasy? 
  2. What is your guilty pleasure?
  3. Is there anything we haven’t tried that you would like to do? 
  4. Where, on your body, is your favorite place to be kissed? 
  5. What is the first thing you noticed about me? 
  6. Have you ever fantasized about another person joining us? 
  7. Have you ever used toys in the bedroom? If so, which one was your favorite? 
  8. Should we bring toys to the bedroom?
  9. Does dirty talk turn you on? 
  10. Where is the weirdest place you’ve had sex? 
  11. What is your favorite thing to do in bed? 
  12. Have you ever had sex with another couple in the room?
  13. When did you realize you were in love with me? 
  14. Do you think there’s a difference between having sex and making love?
  15. How do you describe me to other people? 
  16. Do you like roleplay? 
  17. Have you ever gone skinny dipping? 
  18. Should we watch porn together?
  19. What is something I do in bed that drives you wild, in the best way? 
  20. When am I at my sexiest? 
  21. What is your favorite part of my body? Touch it, rather than say it. 

Questions To Ask Yourself About Your Relationship

If you’ve hitten a roadblock in your relationship or you’re starting to question the person you’re with, take some time for yourself and think about the answers to these questions. These are intimate, deep, serious questions you should be asking yourself about you and your relationship. (Remember, if you feel unsafe or scared by any means, talk to someone who can help you and get out of the relationship if need be.)

  1. Do I like them or am I just bored or wanting attention?
  2. Would I relocate for love?
  3. Are we really compatible? 
  4. Do we have the same views on religion, politics, life? 
  5. Am I satisfied, emotionally, and sexually? 
  6. What was the best moment of our relationship? 
  7. When was the last time they made me cry? 
  8. Would I forgive them if they ever cheated on me? 
  9. Do I look forward to the future with them?  
  10. Do I feel safe in this relationship? 
  11. Can I trust my husband/wife? 
  12. Can I trust my boyfriend/girlfriend? 
  13. Do I really know my partner? 
  14. Would I want to raise kids with them? 
  15. Would I be able to travel with them? 
  16. Is there anyone else I could potentially see myself dating?
  17. Do they make me happy? 
  18. Am I doing everything I can to make them happy? 
  19. Do I love them or see myself loving them? 
  20. Is there anything I should ask them before the relationship can continue?
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50 Questions To Ask The Person You’re Dating

1. What do you think is the most important lesson you can teach a child?

2. What’s one lesson your parents taught you as a child that you believe has shaped who you are today?

3. Who do you feel played the biggest role in shaping the person you are today?

4. What’s one memorable lesson that person taught you?

5. Would you do something that wasn’t ‘allowed’ or ‘accepted’ if it was something you truly believed in?

6. What’s more important to you, telling the truth or little lies to make others happy?

7. Whose happiness is more important, your loved ones’ or your own?

8. What are the things in your life that make you happy?

9. What are the things in your life that make you unhappy?

10. Which do you agree with: When you love someone, tell them when you feel it, or wait for them to say it first?

11. Are you a naturally jealous person?

12. What kinds of things make you jealous in a relationship?

13. What constitutes cheating, or unfaithfulness?

14. If you ever cheated would you keep it to yourself, or confess?

15. Do you consider yourself an affectionate person?

16. In what way do you show affection?

17. What way do you like others to show affection towards you?

18. Do you like to travel?

19. Where’s your favorite place to travel?

20. What would be your dream honeymoon if you ever have one?

21. Is marriage something you want to happen in your lifetime?

22. If so, what kind of wedding do you imagine yourself having?

23. What’s the number one most important quality you look for in a significant other?

24. What’s the number one most important quality you try to embrace for yourself?

25. What’s one thing you would never tolerate in a relationship?

26. Do you consider yourself messy or neat?

27. What is the one ‘around the house’ chore you hate the most?

28. What’s your favorite meal, breakfast, lunch, or dinner?

29. What’s one food you could eat everyday for the rest of your life if you had to?

30. Are you a dessert person?

31. What’s your favorite thing to eat for breakfast?

32. Would you say you’re always early, late, or usually on time?

33. Are you a morning or night person?

34. Do you enjoy cuddling or passionately hate it?

35. If your job asked you to move across the world, would you do it?

36. What’s your dream job/career?

37. What’s more important to you in terms of your career, salary or happiness?

38. Can you imagine yourself as a parent?

39. Do you want to be a parent one day?

40. If so, when do you think you’ll be ready to be one?

41. Would you ever adopt a child?

42. Are you an animal person?

43. How many animals is your ideal number of pets to own?

44. Are you a dog or cat person? Bunnies? Small rodents? Lizards?

45. What’s your favorite exotic animal?

46. If you had to choose, which would you rather know, the day you’re going to die, or the cause of death?

47. Are you a spiritual person?

48. Do you believe in God?

49. Why or why don’t you believe in God?

50. If you could live forever would you?



Awkward silence during small talk is never fun. When a conversation fizzles, you need to ask the right questions to your conversation partner. Whether you’re talking to an old friend or a new person you’ve just met, a good question has the potential to make a conversation last for hours on end.

In order to make you come across as more interesting in any conversation, you should ask an open question that will help you get to know a person better. To help you on your journey, here is a big list of questions to ask to get to know someone:

Jump to: Questions about Likes • Interests • Fun • Family • Love • Values • Aspirations • Deep • Philosophical • Religion • Life • Career

Simple conversation starters about their likes and dislikes:

  1. What is your favorite food?
  2. What is your favorite book?
  3. What is your favorite color?
  4. What is your favorite movie?
  5. What is your favorite thing about summer?
  6. What is your favorite thing about winter?
  7. What is your favorite song to blast in the car?
  8. What is your favorite holiday to celebrate with your family?
  9. What is your favorite memory from your childhood?
  10. Where is your favorite place to vacation?
  11. What was your favorite subject in school?
  12. What is your favorite letter of the alphabet?
  13. What is your favorite podcast to listen to on long drives?
  14. What is your favorite quote from a movie, novel, or show?
  15. What is your favorite number?
  16. What is your favorite candy to eat at the movie theater?
  17. Where is your favorite restaurant to take dates?
  18. What is your favorite homemade meal that your mother cooks?
  19. What is your favorite breakfast cereal?
  20. What was your favorite toy when you were a little kid?
  21. What is your favorite flavor of coffee?
  22. What is your favorite television show of all time?
  23. What is your favorite boy band?
  24. What was your favorite cartoon when you were younger?
  25. What is your favorite state you’ve visited?
  26. What is your favorite ride at an amusement park?
  27. What is your favorite season?
  28. What is your favorite type of flower?
  29. What is your favorite board game?
  30. What was your favorite book when you were little?
  31. Who is your favorite superhero?
  32. Who is your favorite actor or actress?
  33. Who is your favorite athlete?
  34. Where is your favorite place to shop for clothing?
  35. What is your favorite candle scent?
  36. What is your favorite day of the week?
  37. What is your favorite website?
  38. What is your favorite type of car?
  39. What is your favorite ice cream flavor?
  40. What is your favorite way to relax at the end of a long day?

Icebreaker questions about their interests:

  1. What is your guilty pleasure?
  2. What do you do for fun on weekends?
  3. What is your favorite form of social media: Twitter or Instagram or TikTok?
  4. Who is your favorite comedian to watch when you need a laugh?
  5. What’s your favorite sport to play with friends?
  6. What’s your favorite video game to play with friends?
  7. What’s your favorite drinking game to play with friends?
  8. Do you do any volunteer work? Do you donate to any charities?
  9. Who is your closest friend–and what do you like to do together?
  10. What is your favorite type of craft to work on? Painting or writing or knitting or something else entirely?
  11. What show can you watch over and over again without getting bored?
  12. Do you play any musical instruments?
  13. Do you know any other languages?
  14. What genre of books do you usually read in your free time?
  15. What is your favorite form of exercise? Biking or swimming or weightlifting or power walking?
  16. Do you know how to dance? What songs make you want to get up and move?
  17. What hobbies did you have when you were younger that you gave up?
  18. What hobbies did you pick up when you were younger that you still enjoy?
  19. Do you prefer solo hobbies or hobbies that involve big group activities?
  20. Do you enjoy cooking or baking? What’s the most delicious thing you can make?
  21. Do you garden? If so, what types of seeds have you planted?
  22. Do you enjoy hiking? If so, what was the best trail you’ve ever hiked?
  23. Are you a skilled artist? What’s the most impressive thing you’ve ever drawn?
  24. Have you ever gone camping? Do you have any fun stories about the wilderness?
  25. Are you a dog person or a cat person?
  26. What is your favorite conversation topic?
  27. Do you collect anything? Rocks or stamps or Pokemon cards?

Examples of a fun question to spark conversation:

  1. What’s the weirdest thing you believed as a child?
  2. What would be the title of your memoir?
  3. At a party, where can someone usually find you?
  4. What is the funniest name you’ve heard someone call a pet?
  5. If a movie was made of your life, what actor would play you?
  6. If you could have an exotic animal as a pet, what would it be?
  7. Have you ever social media stalked someone?
  8. What is your go-to pose when taking a selfie?
  9. What is your favorite celebrity scandal?
  10. Did you have an imaginary friend when you were little?
  11. What are your favorite three topics to talk about?
  12. What’s your earliest memory?
  13. If there were 26 hours in a day, what would you do more of?
  14. What’s the longest you’ve gone without sleep (and why)?
  15. Aside from necessities, what one thing could you not go a day without?

Examples of a random question that will break the ice:

  1. If you were forced to get a tattoo today, what would you get?
  2. What is your secret, hidden talent?
  3. What’s the last television show you binge-watched online?
  4. How many pets do you have? What are their names?
  5. Do you eat the crusts on your sandwiches?
  6. Who is your hero? Is it a celebrity or someone you know in real life?
  7. How long can you go without checking your phone?
  8. Do you believe in psychics? Have you ever visited one?
  9. If your friends created a band, what would it be called?
  10. What’s your favorite pizza topping? What about ice cream topping?
  11. Do you believe parallel universes exist?
  12. Do you believe aliens exist?
  13. Have you ever seen a ghost in real life?
  14. Do you prefer horror movies or romantic comedies?
  15. What movie ending do you wish you could change?

Examples of a funny question they can answer:

  1. What is the weirdest conversation you’ve ever overheard?
  2. What’s the most ridiculous fact you know?
  3. What is something that everyone looks stupid doing?
  4. If animals could talk, which would be the rudest?
  5. What’s the most imaginative insult you can come up with?
  6. What would be the absolute worst name you could give your child?
  7.  If life were a video game, what would some of the cheat codes be?
  8. What would be the coolest animal to scale up to the size of a horse?
  9.  What set of items could you buy that would make the cashier the most uncomfortable?
  10. Who do you know that really reminds you of a character in a TV show or movie?
  11. What is something that is really popular now, but in 5 years everyone will look back on and be embarrassed by?
  12. Are you the type of person who folds toilet paper over or under?

Examples of a fun hypothetical question for them to answer:

  1. What would be your strategy for a zombie apocalypse?
  2. What two animals would you like to switch the sounds they make?
  3. What cartoon world do you wish you could live in for a week?
  4. If you could put wings on any species of animal, what animal would you choose?
  5. If you could go back in time and give your parents advice before you were born, what advice would you give them?
  6. If you were required by law to get a full body tattoo, what would you get tattooed over your entire body?
  7.  If you could erase one thing from existence, even the memory of the thing, what would it be?
  8. If you were reincarnated as an animal based on your personality, what animal do you think you would come back as?
  9.  If you had to get a tail, what tail would you want and what would you use it for?
  10. If your dog or cat suddenly spoke one sentence and then never spoke again, what would be the most unsettling sentence they could say?
  11.  If you could go back and hands down win any argument you’ve had with anyone, what argument would you choose to win?
  12. If you had to be haunted by a ghost for the rest of your life but could choose which dead person the ghost would be, who would you choose as your ghost?
  13. If you had an animal or plant renamed in your honor, what would you want to carry your name?
  14. If you could choose any job to be replaced by robots, what job would you make obsolete?
  15. What movie-worthy heist would you pull if you knew, in the end, you would get away with it?
  16. If you were given any one luxury item, but you couldn’t sell it, what luxury item would you want?
  17. If you were the next pied piper, what animal would you want to be able to compel to follow you?
  18. If you were a fashion icon and whatever you wore would become a fashion trend, what fashion trends would you start?
  19. If you were chosen to be the first human to make contact with aliens, would you want to?
  20. You get one text, no more than 160 characters, that gets sent to everyone’s phone. What does it say?
  21.  If you died and had to choose one place to haunt for the rest of eternity, where would you choose to haunt?
  22. What amusement park do you wish existed?
  23. If you could change what people say after someone sneezes, what would be the funniest thing for people to say?
  24. If you could bring back any canceled TV series, which TV show would you choose to bring back?
  25. If all animals became as intelligent as humans and were miraculously able to speak, what jobs would be well suited to which animals?

Examples of a rhetorical question that doesn’t require an answer:

  1. Are you kidding me?
  2. Does a bear poop in the woods?
  3. Is rain wet?
  4. Is the pope Catholic?
  5. Is hell hot?
  6. What’s the point?
  7. What’s the matter with kids today?
  8. Who cares?
  9. Why me?
  10. Does it look like I care?

Personal questions about their family:

  1. What is the worst thing about being a middle/only/oldest child?
  2. How much time do you spend with your family each week?
  3. Which family member are you the closest to?
  4. Who do you call on the phone the most often?
  5. What do you wish you could change about your childhood?
  6. What is your favorite family tradition?
  7. Do you want a family of your own?
  8. How did your parents meet?
  9. How did your grandparents meet?
  10. Have you ever been to a family reunion?
  11. How does your family handle arguments?
  12. Do you ever wish you had more siblings?
  13. Who do you consider your family that isn’t actually related to you?
  14. Does your family pressure you to act a certain way? Or do they support your decisions?
  15. Did you have a curfew when you were younger?
  16. Which family member do you look like?
  17. Are you good with children? Do you want any of your own?

Negative questions to avoid asking family members to answer:

  1. Did you lose anyone during the Covid 19 pandemic?
  2. Are you pregnant?
  3. Why are you still single?
  4. Why are you still working at that job?
  5. How many people have you slept with?
  6. When are you going to settle down?
  7. When are you going to have children?
  8. Why aren’t you with your ex anymore?
  9. When’s the last time you got laid?
  10. Are you really wearing that tonight?
  11. Have you had cosmetic surgery?
  12. Are you wearing makeup?
  13. Why are you so dressed up?
  14. Are you going to eat all that?
  15. Who did you vote for in the election?

Sample questions about love and relationships:

  1. What is your biggest pet peeve when it comes to dating?
  2. What is a good way to express love, in your opinion?
  3. Who was your very first celebrity crush?
  4. Do you believe cheaters can change?
  5. When did you have your first kiss?
  6. What gives you butterflies?
  7. What’s the best pickup line you can come up with off the top of your head?
  8. Where is your favorite first date spot?
  9. Who is your favorite fictional couple?
  10. Are you close friends with any of your exes?
  11. Have you ever broken someone’s heart?
  12. How do you feel about sharing your password with your partner?
  13. If you are in a bad mood, do you prefer to be left alone or have someone cheer you up?
  14. How would you describe your first crush?
  15. Do you believe in second chances?
  16. What are your thoughts on online dating?
  17. Is flirting cheating?
  18. Would you go through a partner’s phone if you could?
  19. What’s the biggest lie that a guy or girl you were dating has told you?
  20. What is your love language?
  21. What zodiac sign do you usually have the most chemistry with?
  22. What zodiac sign do you usually clash with completely?
  23. If someone hit you with a flirty pickup line, how would you answer?

Examples of a flirty question to ask a guy:

  1. What is my sexiest personality trait?
  2. What is the craziest thing you’ve ever done in bed?
  3. Where’s your favorite place to be kissed?
  4. What is your naughtiest fantasy?
  5. What is your favorite sex position?
  6. Where is the most adventurous place you’ve had sex?
  7. What’s your favorite song to listen to during sex?
  8. What color underwear are you wearing right now?
  9. What’s your idea of the perfect date?
  10. Have you ever touched yourself while thinking of me?
  11. Are you going to save our text conversation to reread later?

Examples of a direct question to ask a guy you like to make your crush obvious:

  1. What are you looking for in a relationship?
  2. Do you have a specific type?
  3. Do you prefer blondes or brunettes?
  4. Do you like to cuddle?
  5. If we went to the movies, what would you want to see?
  6. If we went bowling, do you think you could beat me?
  7. Do you have my number in your phone?
  8. Did you see my latest selfie on Instagram?
  9. Are you over your exes or still healing?
  10. Are you free this weekend?

Wild questions to ask during a questions game at a party:

  1. Have you ever gone skinny dipping?
  2. Have you ever worn handcuffs in the bedroom?
  3. Have you ever played strip poker?
  4. Do you have any hidden tattoos or piercings?
  5. What is the hardest drug you’ve ever done?
  6. What was the drunkest you’ve ever gotten?
  7. What is the most embarrassing thing that’s happened to you in the bedroom?
  8. Have you ever been to an adult toy store?
  9. When was the last time you wore lingerie?
  10. Have you ever visited a strip club?

Examples of a personal question about a person’s values:

  1. Have your priorities changed since you were younger?
  2. What is one behavior you refuse to tolerate?
  3. What is the most important personality trait that you look for in a friend?
  4. What does a healthy relationship look like, in your opinion?
  5. Do you consider love or money more of a priority?
  6. What was your biggest blessing in disguise?
  7. What did you learn from your last relationship?
  8. What bad habits do you wish you could change?
  9. Does honesty or loyalty mean more to you?
  10. What values did your parents instill in you?
  11. What is an example of a toxic personality trait?
  12. Do you consider yourself a good person?
  13. Have you ever lied to protect a friend or family member?
  14. What material things must exist in your life for you to feel fulfilled?
  15. What is the greatest lesson a teacher ever taught you?
  16. Do you have any regrets about how you’ve treated people in the past?
  17. When was the last time you did a good deed for someone?
  18. What do other people prioritize that you believe is overrated?
  19. What personality trait do you value the most in a friend?
  20. What do you believe your purpose in life is?

Examples of a simple question to ask about someone’s aspirations:

  1. What is on your bucket list?
  2. What makes you feel empowered?
  3. What do you wish you accomplished by now?
  4. Where was your favorite place you’ve ever worked?
  5. What makes you feel the most accomplished?
  6. Who are your role models when it comes to your career goals?
  7. What inspires you when you’re low on motivation?
  8. Out of all your friends, whose accomplishments do you admire the most?
  9. How are you going to make the world a better place?
  10. What kind of example do you want to set for the younger generation?
  11. Are you the kind of person who leads or follows?
  12. What are you the most passionate about in life?

Examples of a great question about making and breaking intentional habits:

  1. What bad habits are you trying to break right now?
  2. What bad habits are dealbreakers for you in a relationship?
  3. What positive habits are you trying to form?
  4. When was the last time you broke a bad habit?
  5. Did you inherit any of your bad habits from your parents?
  6. What is your worst habit when it comes to dating?
  7. What is your best habit when it comes to dating?
  8. What habit have you tried to break multiple times, but have never been successful?
  9. What habits do you want to instill in your children?
  10. What do you think the most important step to breaking a habit is?

Examples of a deep question to ask:

  1. What is your biggest regret in life?
  2. What is the biggest challenge that you’ve overcome in life?
  3. How do you think you’re going to die?
  4. What scares you the most about the future?
  5. What book has had the most profound impact on you?
  6. What makes you feel alive?
  7. How do you want to be remembered?
  8. What do you want to have written on your tombstone?
  9. When was the last time you felt vulnerable?
  10. What do you take for granted?
  11. At what point in life were you the happiest?
  12. What emotion do you experience the most?
  13. What is a dream you’ve never said out loud?
  14. What do you find yourself lying about the most?
  15. Is it easy for you to show yourself love or speak kindly to yourself?
  16. What do you use to cope when you’re feeling uncomfortable?
  17. Who is the first person you call when you’re in trouble?
  18. What are you most grateful for in your life?
  19. Do you usually follow your heart or your head?
  20. Did you ever judge someone for the dark secrets they told you?
  21. How long does it take you to trust someone?
  22. What do you do when you’re angry?
  23. What was the worst phase of your life?
  24. When have you felt your biggest adrenaline rush?
  25. What do you hope to have achieved by 50?
  26. Is there an opportunity you turned down that you secretly wish you’d have taken?
  27. Is there a time or event in your life that you wish you would’ve appreciated more?
  28. What do you miss about being a kid?
  29. What’s the most spontaneous thing you’ve done lately?
  30. When was the last time you lied about being fine and why?

Examples of an interesting question to ask during a conversation:

  1. Would you sacrifice yourself for another person? Who?
  2. When is it okay to break the law?
  3. What do you want your last words to be?
  4. When was the last time you pushed yourself to your limits?
  5. Do you believe street smarts or book smarts are more useful?
  6. Do you think artificial intelligence is going to overpower us?
  7. Is privacy a human right?
  8. Are people mostly good or mostly evil?
  9. Do you believe immortality would be worth it?
  10. What is the difference between living and existing?
  11. Does a person’s name influence the person they become?
  12. Does hardship actually make a person grow stronger?
  13. Is humanity headed in the right or wrong direction?
  14. What do you contribute to society?
  15. What do you think your future self will remember about this period of your life?
  16. How do you define consciousness?
  17. Would it be more frightening to discover that humans are the most advanced species in the universe or that we are far from being the most advanced species in the universe?
  18. Why do humans have such a strong urge to distract ourselves from the real world?
  19. What’s the difference between justice and revenge?
  20. What would be the most ethical way to give away five million dollars?
  21. Are all individuals morally obligated to save another person’s life if they are able?
  22.  Does anonymity encourage people to misbehave or does it reveal how people would choose to act all the time if they could?
  23. Why are humans so fascinated by mass murderers if their actions are universally considered evil and vile?
  24. Is it better to be a big fish in a small pond or a small fish in a big pond?
  25.  If you could teach everyone in the world one concept, what concept would have the biggest positive impact on humanity?
  26.  Is it more important to help yourself, help your family, help your society, or help the world?
  27. Is it wrong to spend money on expensive food when people are dying of hunger?
  28. Can computers be creative?
  29. If lying is wrong, are white lies okay?
  30. What is the meaning of life?

Existential questions about religion and the afterlife:

  1. What religion do you practice?
  2. What do you believe happens after someone passes away?
  3. What is your favorite quote from a religious text?
  4. How often do you pray?
  5. Which religious holidays do you celebrate?
  6. Are your parents also religious?
  7. If you believe in heaven, what do you think it looks like?
  8. If you believe in hell, what do you think it looks like?
  9. Do you care if your friends practice different religions than you?
  10. Could you date someone who practiced a different religion than you?
  11. Are you planning on passing down your beliefs to your children?
  12. How are you going to answer your calling in life?
  13. When do you feel the most connected to a higher spirit?
  14. How has your faith helped you?
  15. How has your faith hurt you?

Follow up questions to ask younger children and teenagers about life:

  1. Are you a good student?
  2. Have you ever flunked a quiz?
  3. Have you ever gotten detention?
  4. Do you have any nicknames?
  5. What’s your favorite phone game?
  6. What are the best filters to use on social media photos?
  7. What shows is everyone at school watching right now?
  8. Have you read any good books in class lately?
  9. Who is your favorite teacher?
  10. What fashions are popular nowadays?
  11. What is your favorite new slang word?
  12. Do you put more energy into making friends, dating, or getting good grades?
  13. Are you taking any classes that you wish you could drop out of?
  14. Do you feel like the grading system is fair?
  15. Do you prefer texting or talking to people face-to-face?
  16. Do you feel pressured to look perfect on social media?
  17. What do you wish your parents understood about you?
  18. Do you think you’re given too much homework?
  19. What is your favorite thing to do on weekends when you’re by yourself?
  20. Do you know what you want to do when you’re older?

Examples of a leading question that will guide a conversation and give you the answer you want:

  1. You live in my town, don’t you?
  2. You have a dog, too, don’t you?
  3. You’re a fan of (insert band), right?
  4. You’re obsessed with animals too, aren’t you?
  5. We’re in the same classes, aren’t we?
  6. You’re a coffee addict too, right?
  7. You’re my age, aren’t you?
  8. You watch (insert show) too, don’t you?
  9. We have a friend in common, don’t we?
  10. You’re into (insert sport) too, right?

Casual questions to ask about a friend’s career:

  1. What is your dream job?
  2. When you were little, what did you want to be when you grew up?
  3. What has been your greatest accomplishment in life?
  4. What’s the most embarrassing thing you’ve said during a job interview?
  5. Have you ever sent the wrong text to one of your employers?
  6. What’s your favorite thing about your current job?
  7. Who is your favorite coworker?
  8. Would your younger self be proud of what you’re doing now?
  9. What career advice would you give your younger self?
  10. Are you proud of yourself? Why or why not?
  11. What does success look like to you?

Examples of an open ended question to ask when speaking to a customer:

  1. What are your thoughts?
  2. What concerns do you have?
  3. What is most important to you at the moment?
  4. What challenges are you facing?
  5. What would you change about your current situation?
  6. Where do you turn for inspiration?
  7. What are your top priorities?
  8. What goals would you like to accomplish?
  9. Where did you look before coming to our store?
  10. How can we make this webpage/store better?

Examples of a job interview question you might be asked to answer during an interview:

  1. What is your salary expectation?
  2. Why do you believe you’re a good fit for this company?
  3. What’s an example of a time you went above and beyond for a customer?
  4. What is your greatest asset as a team member?
  5. Where do you see yourself in the next few years?
  6. What is your greatest weakness?
  7. Why are you leaving your current position?
  8. What interests you about this role?
  9. Do you know how to properly use any internet device?
  10. What motivates you to work your hardest?
  11. As your interviewer, do you have a specific question you want to ask me?

Questions you should ask during an interview about company culture:

  1. What do you consider the greatest benefit of working here?
  2. What is your favorite thing about being a hiring manager?
  3. What role do you play at this company?
  4. Has your role changed since you’ve been here?
  5. What can someone do to impress you during the interview process?
  6. Who will I, and the other participants, report to directly?
  7. What are the common career paths in this department?
  8. What’s your least favorite part about working here?
  9. Can you tell me about the last team event you did together?
  10. Where do you see this company in the next few years? Thought Catalog Logo Mark

Catalog questions thought

The Secret To A Lush Date Conversation Has Nothing To Do With Words

The questions you ask on a first date will make or break the vibe as you get to know each other. If you want your date to go well, study these questions beforehand. The right first date questions will help you make the best impression possible.

Genuinely Interesting Questions For You To Ask Your Next Date

It’s really, REALLY attractive when people ask well thought out questions on a first date that at least give the illusion that they want to know you better—not just know where you went to college and what your worst OkCupid story is. Good questions like the below are sexy. So if you want to impress your next first date, memorize at least a few of them.

1. Who inspires you? Who do you aspire to be like?

2. What was the last book you read without skipping through anything?

3. What is the weirdest scar you have and how did you get it?

4. What is the most random thing you’ve ever watched all the way through on Netflix?

5. If you could trade lives with one person for an entire day who would it be and why?

6. Do you believe in ghosts?

7. Shark diving, bungee jumping, or sky diving?

8. Which would be harder for you to give up: coffee or alcohol?

9. How did you meet your best friend?

10. Do you have a sweet tooth or a savory tooth?

11. What is something you’ve always wanted to try but have been too scared to?

12. What accomplishments are you most proud of?

13. If you were going to go to the movies alone, what would be the perfect film for you to watch by yourself?

14. What is your favorite Wikipedia article? (Shuddup. Everyone has one.)

15. What is your favorite physical attribute about yourself?

16. Tell me about the best vacation you’ve ever taken.

17. Where is your favorite place to go on a weekday afternoon when you have no plans or obligations?

18. What is one of the weirdest things you used to do as a teenager?

19. Gin, vodka, or tequila?

20. What drives you to do what you do? What motivates you?

21. In your opinion, what is the best Disney movie to come out since Disney’s Golden Age?

22. What kind of phone was your first cell phone?

23. What did you love most about the place you grew up? What about it did you love the least?

24. What trajectory are you hoping to push yourself onto? Where do you want to head?

25. What is your most bizarre talent?

26. Is there a documentary or book that really changed the way you thought about something?

27. What are three albums (soundtracks or compilations don’t count) that really define you or have shaped you as a person?

28. Who was someone you really looked up to when you were little — someone you considered to be a mentor?

29. What’s your favorite cheesy pick-up line? Have you ever used it for real?

30. Who is a character from a TV show or a book that you’ve always resonated with?

31. Can I get you another drink?

32. Ask them to give you two “truths” and a lie. Then try to guess which one is a lie.

33. If you could write a note to your younger self, what would you say in only two words?

34. If you had to name one thing that really makes your day, what would it be?

35. What is a misconception others often have about you?

36. Whats the most valuable life lesson you have learned because of a mistake?

37. What’s an accomplishment you are really proud of?

38. Read anything interesting lately?

39. What’s one thing you wish you had known as a freshman in college?

40. What is one day you would love to relive? (This will tell you something near and dear to your their heart in a fun way).

41. When it comes to love and relationships, what is the first lesson you want to teach your children?

42. If you could change one physical & non physical thing about yourself, what would it be?

43. What should I know about you that I’d never think to ask about?

44. What do you hate most about the dating process? (You want them to tell you so you can avoid it) ;)

45. What is #1 thing in your life that you are not doing that you wish you were?

46. What do you do when you feel like giving up?

47. If you could only keep one book you currently own, what would it be?

48. What are you most excited about in your life right now?

49. Describe one extravagance you have for which you will never apologize.

50. What do you want to be known for?

51. In one sentence what is your biggest concern right now?

52. Complete the following: There would be fewer divorces in this country if only people ________.

53. What’s something that you sometimes outwardly wish more people realized about you, but you’re happy is internalized because to be able to sit on this information makes you stronger?

54. How many times have you been in love & what did each experience teach you?

55. What’s something that comes easier to you than it does for most?

56. What do you feel people take for granted the most?

57. What are you better at than 90 percent of the population?

58.What is something about you that would surprise me?

59. What is a piece of advice you often give but find yourself struggling to follow?

60. Describe your perfect mate in one sentence.

61. When is the last time you did something courageous for yourself?

62. On a scale of one to ten, how happy are you? (Then sit silent and wait for their answer. The pause is important).

63. Whats the stupidest thing you’ve ever done for love?

64. What’s something many people fear that doesn’t scare you at all?

65. What’s something that instantly makes someone less attractive?

66. Would you describe yourself as more of an optimist, a pessimist, or a realist?

67. What would be a question you’d be afraid to tell the truth on?

68. What is something you wish you did more of in your life and something you wish you did less of?

69. Which significant other in your life has had the biggest impact on you and why?

70. What is a piece of advice that you were given that if you listened to it, you would not be where you are today?

71. If you had to spend a year alone with one other person who would it be and why?

72. What was the last thing you learned that made a big impact on you or an ah-ha moment?

73. If you only had 30 seconds to share one if the most important things you’ve learned with the world, what would it be?

74. What’s one fear you know is holding you back?

75. What was the last mistake you made that you’re sure you’ll probably make again?

76. When was the last time life left you breathless?

77. What are you really passionate about and why?

78. What’s the best advice someone has ever given you?

79. Where is your favorite travel get-away?

80. If you had one hour left to live what would you do?

81. What was your favorite year and why?

82. If you could meet someone who’s dead who would it be?

83. Do you have any tattoos? What do they mean?

84. If you could come back to life as an animal what animal would you be?

85. What’s one song you really relate to?

86. What was the last movie that made you cry? Or the last movie that made you emotional (for people who are too embarrassed to admit a movie made them cry)?

87. If you could be friends with a celebrity who would it be and why?

88. Have you ever laughed so hard you peed your pants? (Then ask what made them do it)

89. If I were to ask your friends about you what would they say?

90. What’s something you would never want your mother to know about you?

91. What is something you’ve never done that you’ve always wanted to do?

92. If you could live another life as someone else who would it be?

93. If you could change one thing about the world what would it be?

94. When was the last time you cried?

95. What do you think happens to us after we die?

96. What is your drink of choice?

97. What was your favorite game to play as a child?

98. Do you have any embarrassing nicknames you’d like to share? How’d you get them?

99. Dog or cat person?

100. What is one TV show you’re embarrassed to admit you watch?

101. What’s your favorite guilty pleasure food-wise?

102. What’s one book you’ve read that has caused some deep thinking?

103. What’s your most used emoji?

104. If you could pick an emoji to best describe you which one would it be?

105. What’s one character (could be from TV, a movie, or book) you identify with?

106. Have you ever broken a bone? How?

107. Coffee or tea?

108. If a high-school stereotype were to describe you in adulthood which one would it be?

109. Are you a morning or night person?

110. If you won the lottery, what’s the first thing you would buy?

111. What’s your favorite season?

112. Do you prefer hot or cold weather?

113. Would you rather live forever or die tomorrow?

114. What’s one lie you’ve told that you were caught in?

115. Who in your family are you closest to?

116. What would you say is your most redeeming quality?

117. What has been your biggest accomplishment in life so far?

Essential Get-To-Know You Questions You Can Rely On For Every First Date

First dates are nerve-wrecking. But they’re a whole lot less nerve-wrecking if you’re armed with the right questions to ask. These first date questions will help you get to know the person sitting across from you at the dinner table faster than usual.

118. What three U.S. cities would you never, ever move to even for the job offer of your dreams?

119. What combination of fixings makes your perfect burrito?

120. What is the best gift you’ve ever received?

121. What is the most thoughtful gift you’ve ever given?

122. Who is your role model or has had the biggest influence on your life?

123. Do you have any nicknames?

124. What’s one thing you wish you had known as a freshman in college?

125. How many siblings do you have?

126. Do you consider yourself a morning person or a night owl?

127. How long did it take you to start enjoying coffee?

128. What do your parents do for a living?

129. What quality is your automatic “no fucking way” when pursuing a potential relationship?

130. What are two of your bucket list items?

131. Have you ever kept a New Year’s resolution?

132. Were you closer with your mom or your dad growing up?

133. What is something you are financially saving up for currently?

134. Where is your happy space?

135. What is your favorite article of clothing you own?

136. Do you have any specialty cooking dishes?

137. What is one job you could never do?

138. When is your birthday?

139. What is in your fridge right now?

140. What are you worse at than 90 percent of the population?

141. Do you believe in aliens?

142. Do you think it’s the little things or grand gestures that count the most?

143. Have you ever been out of the country?

144. What fact about you surprises people the most?

145. What do you do for a living?

146. What’s the most spontaneous thing you’ve ever done?

147. What’s your ideal vacation?

149. If you could live in any other U.S. city, which city would you live in?

150. What was your favorite family vacation growing up?

151. Are you a big fan of any major pro sports team?

152. What was your favorite subject in school?

153. What are you better at than 90 percent of the population?

154. If you could travel back to any one point in time what would it be?

155. What is the proudest moment or greatest achievement of your life so far?

156. How did you meet your best friend?

157. If you could be any animal, what would you be?

158. Salty snacks or desserts?

159. What is a family tradition your family has?

160. What do you think is the most important life lesson for someone to learn?

161. What was your favorite toy growing up?

162. Who was your favorite teacher or professor?

163. What is the best advice you’ve received?

164. What’s the luckiest thing that’s ever happened to you?

165. What do you feel people take for granted the most?

166. What do you like the most about (insert city of residence)?

167. What is the craziest scene or event you have ever witnessed?

168. What is your biggest pet peeve?

169. What was the worst job you’ve ever had?

170. What was the last book you read?

171. When you were younger, what did you want to be when you grew up?

172. What was something that recently moved you?

173. What skill or talent do you wish you had or were better at?

174. If you just won $1 million, what would you do with it?

175. If you could have a superpower what would you want it to be?

176. What are you passionate about?

177. What is your favorite movie?

178. Are you a cat person, a dog person, both or neither?

179. What do you think is your greatest strength?

180. If you had to be a vegetable, which vegetable would you least like to be?

Fun Questions To Ask On A First Date To Start (And Keep) A Good Conversation Going

Conversations tend to lull every so often, especially with people you don’t know all that well. When you’re on a first date, it’s a good idea to ask lots of questions so you can kickstart a good conversation and / or keep it going.

181. If you could invite five people, dead or alive, to a dinner party, who would you choose and why?

182. When you were little, where did you think you’d be by now? Are you there?

183. What was the last dream you had?

184. If you could start a band, what kind would it be and would you name it?

185. Were Ross and Rachel on a break?

186. What was the first album you bought, and why did you buy it?

187. It’s your 75th birthday. Where do you see yourself?

188. What is your favorite mistake?

189. Who do you look up to of the same sex?

190. Who is your role model of the opposite sex?

191. It’s New York City in the 1920’s. What are you doing?

192. What is your favorite book?

193. What is your guilty pleasure song?

194. What was a situation that you initially thought was terrible, but ended up being a blessing in disguise?

195. What’s your favorite word?

196. If you could choose a decade to grow up in, which would you choose?

197. What was your first concert?

198. The stupidest thing you’ve ever spent money on?

199. What would your superpower be?

200. And your superhero name?

201. If you could live in any city, which would you choose? Why?

202. Could you spend a day without your phone?

203. What about a week?

204. The Rolling Stones or the Beatles?

205. If you could be a type of beer, which would you be? Why?

206. If you could live in any fantasy world, be it Hogwarts or Narnia, where would you choose? Why?

207. What is the last book you read? Did you like it?

208. If you could have any talent, which would you have?

209. What was your AIM screenname? Why did you choose it?

210. Would you like to go out again next week?

211. If you were stranded on an island, what is one item you would take with you?

212. Who is your favorite band or musician?

213. Are you more of a morning person or night owl?

214. Where would you go on your dream vacation?

215. Who is the closest person to you and why?

216. Who inspires you?

217. What is your favorite childhood memory?

218. What kind of hobbies do you enjoy?

219. Do you have any fears? If so, what are they?

220. What are your current goals in life?

221. Do have a favorite color and why?

222. What would you choose as your top meal?

223. What is your favorite city you have been to?

224. What is on your bucket list?

225. If you had no fears, what would be the first thing you would do?

226. Do you have siblings?

227. Where did you grow up at?

228. What do value in others?

229. What is your favorite book you have read?

230. What is one piece advice you would give to someone?

231. If you didn’t have to work, what would you do for a living?

232. What is your favorite cuisine to cook?

233. Do you have any vices?

234. What’s one thing you cannot live without?

235. Do you speak any other languages?

236. What is your favorite movie?

237. If you had to describe yourself in three words, what would they be?

238. What is your astrology sign?

239. Do you have any awkward family traditions?

240. If you were an animal, what would you be and why?

241. Do you have any pets?

242. Are you an introvert, extrovert, or ambivert?

243. How long have you lived here?

244. Have you ever lived in another country?

245. Are you more of an indoors or outdoors person?

246. What is your favorite athletic activity?

247. What are you known for amongst your friends?

248. How do you unwind?

249. What are you most grateful for?

250. What is your favorite holiday? How do you celebrate it?

251. What is the most interesting fact about you?

252. If you were to go on a road trip, where would you go?

253. Who has impacted you the most in life?

254. What is one thing you still want to learn?

255. What is your favorite way to spend your time off?

256. What brings you happiness in life?

257. Do you have any pet peeves?

258. If you were to be notable for something what would it be?

259. What’s one thing you practice on a daily basis that improves your life?

260. What is the longest timespan you could live without your phone?

Deep First Date Questions That’ll Put Your Chemistry To The Test Right Away

If you’re one of those people who would rather skip the small talk and get right to the chase, these are the first date questions to ask. If you get through enough of these first date questions, you’ll have a much better sense as to whether or not the relationship will happen, and whether it’ll last.

261. What do you hate the most about modern dating?

262. Has a book ever changed your life?

263. Do you believe in love at first sight or do you think it’s bullshit?

264. If aliens came to Earth, would you be scared of them or would you welcome them?

265. Has a song ever made you cry?

266. Why do you get up in the morning?

267. What’s the most inspirational saying you’ve ever heard?

268. What’s the worst thing that you’ve ever done?

269. If you could rewind time, what one moment would you want to relive?

270. If you were famous, would you still want a relationship or would you sleep around?

271. If you were free to murder one person without getting punished, would you?

272. Do you think people are born good or born evil?

273. Have you ever had a near-death experience?

274. Would you rather be hideous or illiterate?

275. Have you ever had your heart broken?

276. What’s the sweetest gift you’ve ever given your mother?

277. What was the first thing you masturbated to?

278. Are you proud to tell people about your job or embarrassed about what you do?

279. Do you think an animal’s life is just as valuable as a human’s life?

280. Has a celebrity’s death ever caused you to cry?

281. Do you resent your exes or do you wish them well?

282. If you got a girl pregnant, would you consider it a burden or a blessing?

283. Do you like what you see when you look in the mirror?

284. Have you ever written poetry? What about song lyrics?

285. Who would you call if you only had moments left to live?

286. Do you believe in magic?

287. Do you believe in the afterlife?

288. Do you usually go with your gut or with your brain?

289. What celebrity do you think deserves more attention?

290. Have you ever questioned your sexuality?

291. Is there anyone in this world that you genuinly hate?

292. Would the childhood version of you look up to the current version of you?

293. How are you going to leave your mark on the world?

294. Would you lie to keep your best friend out of prison?

295. What type of imaginary scenarios do you create in your head?

296. What’s the earliest memory you have of life?

297. What’s the most important thing on your bucket list?

298. Do you consider yourself to be a good person?

299. Do you think you have a purpose in life?

300. Do you think you’d be capable of murder?

301. Do you believe men and women can “just” be friends?

302. Are you following your dreams or have you given up on them?

303. Which gender stereotype about men do you hate the most?

304. If you could erase specific memories from your mind, would you?

305. Do you love your pets as much as you love your human family members?

306. Have you ever seen a ghost? If not, do you believe they exist?

307. Which fictional character do you relate the most to?

308. Would you choose to live forever if you had the opportunity?

309. Who was your hero when you were a little kid?

310. How do you feel about me?

311. Is it obvious that I’ve dressed up for this special occasion?

312. Have you tried to Google me?

313. Will you believe me if I say I didn’t totally check your social media accounts on my way here?

314. Does anyone know you’re on a date right now?

315. How long have you prepared for this date?

316. Do you easily get bored?

317. Can we try not to touch our phones for half an hour?

318. What’s your first impression of me?

319. What do you like about me so far?

320. Do you feel things deeply? Immensely? Greatly?

321. Have you tried suppressing your emotions? Has it worked?

322. Are you okay talking about feelings?

323. What are your thoughts about someone who’s a chronic over-sharer? Just curious.

324. Do you stare at your ceiling before you sleep?

325. Which has a higher spot in your priority — relationship or career?

326. Are you one of those people who consider dates as job interviews?

327. Okay…so how many dates have you been on before this?

328. How many hearts did you break in the past?

329. What’s your point of view about the idea of forever?

330. When is the right age for you to settle down?

331. What would you do if I just start crying and screaming right now?

332. Do you believe in astrology? When’s your birthday?

333. If I tell you our zodiac signs are super compatible, will you agree on a second date?

334. Have you ghosted someone before?

335. Who has been the biggest influence on your life?

336. What’s your favorite place in the entire world?

337. What really makes you laugh?

338. What’s your favorite movie of all time?

339. What’s your favorite book of all time?

340. What’s your biggest goal right now?

341. What’s your favorite way to spend a weekend?

342. What should I know about you that I would never think to ask about?

343. Have you traveled anywhere really cool lately?

344. Is there anywhere else you would love to live, other than here?

345. What’s on your bucket list?

346. What’s your favorite thing about your job?

347. What is the most thoughtful gift you’ve ever received?

348. What do you feel most passionate about?

349. What’s something you’ve been really proud of lately?

350. What’s something you’ve always wanted to try?

351. What’s one of your favorite childhood memories?

352. What is your favorite thing to cook?

353. What’s your favorite piece of clothing that you own?

354. What is your absolute dream job?

355. Do you consider yourself spontaneous, or a planner?

356. What quality for you is an automatic “no way” when pursuing someone in a relationship?

357. How would your best friends describe you?

358. What is the best single piece of advice you’ve ever received?

359. What is a tradition your family had when you were a kid?

360. What was the worst job you’ve ever had?

361. When you were a kid, what did you hope to do when you grew up?

362. What is one skill you wish you could be better at?

363. If you could donate to any charity, which charity would it be and why?

364. In one word, how would you describe yourself?

365. What do you find most attractive in a potential partner?

366. If you were stuck on a deserted island, who would you choose to have with you?

367. For what in your life do you feel most grateful?

Somewhat Whacky But Absolutely Vital Questions You Must Ask On A First Date

If you’re kind of a weirdo and you want your date to know it, these are the first date questions that will help you let your freak flag fly.

368. How many times a day do you try and use The Force?

369. Gun to your head, must choose one: garlic bread or cinnamon rolls?

370. What’s your opinion on sweatpants?

371. Do you cheat when playing Monopoly most of the time or all of the time?

372. Bulbasaur, Squirtle, or Charmander?

373. You spot a terrifying-looking spider a foot away from you. How do you react?

374. On a scale of 1-10, how much do you drench your pancakes in syrup? (1 being “a lot” and 10 being “Syrup with a side of pancakes.”)

375. On average, how long does it take you to cry yourself to sleep every night?

376. Orange Is The New Black or House of Cards?

377. On average, how many hashtags do you include on an Instagram photo?

378. Who’s your favorite Game of Thrones character? Tyrion or Tyrion?

379. What’s the longest amount of time you’ve spent binge watching something?

380. Who are your favorite celebrity twins and how many days has it been since you last watched Passport to Paris?

381. At what point in the afternoon do you change out of your pajamas?

382. How many sauce packets do you ask for with an order of chicken nuggets?

383. Was Leo still in a dream at the end of Inception?

384. Would you say that Cloris Leachman is basically Betty White’s rebellious cousin?

385. Which Disney villain would you play tetherball with?

386. When a friend pulls you onstage for karaoke, how many lines do you sing before you stab yourself with a stirring stick?

387. What’s the last funny prank you pulled on a friend or family member?

388. What’s the weirdest thing someone’s caught you doing?

389. Where would you go if the zombie apocalypse happened right this second?

390. Was there enough room for Jack on that floating door that saved Rose?

391. Were Ross and Rachel on a break?

392. What’s your favorite thing to do when no one’s looking?

393. What’s your most irrational fear?

394. What’s your mom’s favorite memory of you as a kid?

395. What’s the most embarrassing thing that’s ever happened to you?

396. What’s the greatest trick that’s ever been played on you?

397. What superlative would you award each of your parents and why?

398. What’s your favorite way to eat ice cream?

399. What food can you just not resist?

400. What cartoon character do you most identify with?

401. If you were a carbonated beverage, which one would you be? Thought Catalog Logo Mark

Questions To Ask A Girl With Charly Jordan

140+ Best Funny Questions to Ask Anyone [2020]

These questions from Ask Reddit are going to give you a lot to talk about over dinner tonight!

1. Which parallel universe versions of yourself would you want to meet and why?

2. If you had all the resources, time, and land available to build whatever you wanted (a house, a park, a monument…), what would you build?

3. What are your thoughts on life on other planets?

4. What do you love most about yourself?

5. If you could teach the entire world just one concept, what would it be?

6. What’s something you wish was socially acceptable?

7. What weird habits did you have as a kid?

8. What’s the first thing you think of when you wake up most days?

9. How do you handle your anger?

10. What is your idea of happiness?

11. What’s the most difficult decision you’ve had to make to see your dreams come true?

12. Before making a telephone call, do you ever rehearse what you are going to say? Why?

13. Do you have a secret hunch about how you will die?

14. If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?

15. What do you value most in a friendship?

16. If you could change anything about the way you were raised, what would it be?

17. If you could spend 24 hours inside the world of any painting, which one do you choose and why?

18. If you could kill one person with no social, legal, moral, or religious repercussions who would it be and why?

19.What level of toastiness do you like your toast?

20. What’s the hardest you’ve laughed?

21. What do you do when you’re home alone?

22. If you had a million dollars to donate, what charity would you donate to and why?

23. Who is your favorite Disney villain?

24. What are you watching on Netflix right now?

25. What is the worst thing someone could do on a date with you?

26. What is your ex’s version of that breakup?

27. What’s a fact that makes people wonder why you know that?

28. What do you think happens after we die?

29. What has been the best part of this year?

30. Have you ever read a book that changed the way you thought?

31. Do you find it easier to gain knowledge through books or hands-on experience?

32. When you just want to be left alone, where is your favorite place to be?

33. What’s your definition of hell?

34. If you were an animal, what would you be?

35. If you changed your name, what would it be?

36. What’s something that freaks you out for no good reason?

37. Who’s your favorite Pokemon?

38. What makes you feel at peace?

39. Why is your favorite book/movie/game your favorite?

40. What fictional character do you relate to the most? Thought Catalog Logo Mark


You will also be interested:

300+ Best Conversation Starters for Any Situation

These ridiculous questions from Ask Reddit are sure to break the ice!

1. What’s the most obscure fact you know that would make you win on Jeopardy?

2.What is your favorite version of the potato?

3. If I gave you the money to set up a theme restaurant or bar, what would be the theme? What would you call the establishment? What would be the signature cocktail?

4. If you could only eat one type of cheese for the rest of your life, which type of cheese would it be?

5. What’s the coolest place you’ve taken that pair of shoes?

6.When’s the last time you saw a monkey?

7.If you were a guest on a late-night talk show, what story would you tell?

8. Who’s the artist you’ve listened to the most in the past month?

9. Please rank: Pizza Hut, Dominos, Papa John’s, Little Caesars.

10. If you could reshoot any film, shot for shot with the cast of the looney toons, which film should you pick?

11.Do you have an internal monologue? Like, do you think in words, images, some other way?

12. When you put your socks and shoes on, do you do: sock, shoe, sock, shoe or sock, sock, shoe shoe?

13.Would you rather drink Pepsi or Coca-Cola?

14.What’s your opinion on cows?

15.Who is your favorite villain?

16. If you had to be half lobster, would you want your top half or bottom half to be lobster?

17. Compare yourself to a lead character from a movie.

18.What is your favorite video game?

19. Do you believe in aliens? Why or why not?

20. Are you a Goldfish or Cheez-It kind of person?

21.What’s your oldest memory?

22.Tell me a memory you have about fruit.

23.What is something you can talk/rant about for 10 uninterrupted minutes and still have more to say?

24.What are two facts about yourself that are true, but also seem contradictory?

25.What do you dream about?

26. What’s the best thing that happened to you today?

27.Have you read any good books recently?

28.What’s in the trunk of your car right now?

29. What is your ‘everyday superpower’? (My SO always gets amazing parking, and always picks the fastest line at the supermarket.)

30.What’s your favorite breakfast food?


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