100 Questions to Ask the Guy You’re Talking To
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As a person who identifies as socially awkward, here’s one thing I know to be true: talking is hard. Talking can be especially hard when the person you are talking to is one you have a crush on, recently started dating, and/or are trapped with in the dreaded “talking stage.” Even if you’re someone who doesn’t usually sympathize with the plight of the socially inept (cool, must be nice for you, can’t relate), there’s something about navigating a new fling that can turn even the most gifted conversationalist tongue-tied. This, friends, is why it’s wise to keep a handy list of questions to ask a guy in case you need to smooth over any momentary lulls in conversation.
Pro tip, asking questions is the secret to both keeping a conversation going and, most importantly, keeping it interesting. If there’s one thing people love, it’s talking about themselves, which means that if you give a guy the opportunity to do that by asking thoughtful, open-ended questions, you can trick him into thinking you’re a great conversationalist. JK, you actually will be, because the real trick to smooth talking is simply being interested in what the other person has to say. One way to express interest and also actually learn more about the guy you’re talking to? Ask him questions. (Ideally, of course, he will return that interest and reply with questions of his own for you because, hi, that’s what a conversation is and no one actually wants to date a guy who talks about himself all day.)
Now, you don’t want to just rattle off random questions at the dude like it’s an interrogation. (That said, suggesting a round of 20 Questions is actually a great way to revive a fading text sesh.) Ideally, you’ll want to uh, pay attention to what he’s saying and respond with relevant Qs that encourage him to go into more detail. But if you need to break an awkward silence or rekindle a flagging convo, dropping a fun and thought-provoking question can be just the thing to get the vibes back on track.
Should you find yourself in need of a little inspiration, here are literally 100 questions to ask a guy, from light and low key to fun and flirty to hot and heavy. Keep these in mind for your next date night or sprinkle them into tonight’s texting convo, and I can assure you no awkward silence will go unfilled.
Fun Questions to Ask (for Good Vibes Only)
1. What’s your zodiac sign? (If he responds to this with some kind of eye-roll and/or stereotypical anti-astrology dude comment, that tells you everything you need to know.)
2. Moon sign? (Bonus points if he also knows his rising, obvs.)
3. What’s the number one thing you got in the most trouble for at school?
4. What were you like in middle school/high school?
5. What’s one thing your parents don’t know about you?
6. What are your top three vices?
7. What’s your personality test of choice? (Is he a Myers-Briggs guy? An astrology fan? An Enneagram devotee?)
8. Do you think you’re a good driver?
9. What kind of person are you at parties?
10. What’s your drink of choice?
11. If you could only eat one thing for the rest of your life, what would it be?
12. What’s your most controversial opinion? (We’re talking like, “I don’t actually like dogs that much,” not like, “I don’t think women deserve rights,” BTW.)
13. If you could get on a plane right now and go anywhere, where would you go?
14. Have you ever done anything illegal?
15. Do you remember your dreams?
Flirty Questions to Ask (When You Wanna Be Cute)
16. Do you remember your first kiss?
17. Who was your first crush?
18. How do you know when you have a crush on someone?
19. Do you believe in love at first sight?
20. Have you ever been in love?
21. When was the last time you were in love?
22. What’s one thing you haven’t told me that you want to?
23. What do you think makes a good kisser?
24. Who is your celebrity crush?
25. Where would you take someone on a first date if you were trying to impress them? (Excellent way to inquire yourself into an impressive first date—hint hint.)
26. What’s your love language?
Sexy Questions to Ask (When You Want to Heat Things Up a Bit)
27. What physical feature are you most attracted to?
28. If you could only have sex in one position for the rest of your life, what would it be? (This is a more fun twist on the classic “What’s your fave position?”)
29. What do you think makes someone good in bed?
30. What do you think makes you good in bed?
31. What’s the weirdest place you’ve ever had sex?
32. What do you remember most about the first time you had sex?
33. What sex position/sex act do you think is overrated?
34. What’s something you wish you knew about sex before you had it for the first time?
35. What kind of porn do you watch?
36. What do you masturbate to? (Porn? Imagination? 18th-century erotica?)
37. Do you consider yourself kinky?
38. What’s one thing you were surprised to find out you were into in bed?
39. What’s the number one thing on your sex bucket list right now?
40. Thoughts on group sex?
41. What’s one sex thing you’ve tried and don’t want to do again?
42. Do you have sex dreams?
43. Do you prefer morning sex or night sex?
44. Shower sex: hot or overrated?
45. How often do you masturbate?
46. Do you like to initiate?
Deep Questions to Ask (When You’re Ready to Get Into It)
47. What’s one thing you would change about your childhood?
48. Which of your parents are you closest to and why?
49. Which of your siblings are you closest to and why?
50. What’s your biggest regret from your last relationship?
51. Why did your last relationship end?
52. What’s one thing you would say to your ex if you could?
53. If you could go back in time and say one thing to anyone from your life, living or dead, what would it be?
54. What’s your favorite thing about your best friend?
55. What’s your favorite thing about yourself?
56. What do you think is your worst quality?
57. What is the biggest misconception people have about you?
58. What’s your biggest fear?
59. What’s the hardest thing you’ve ever been through?
Questions About Dating and Relationships (So You Know What You’re Getting Into)
60. Do you consider yourself a relationship person?
61. Do you usually get broken up with or do the breaking up?
62. What makes a relationship “serious” in your opinion?
63. What are your thoughts on open relationships/non-monogamy?
64. Do you like dating apps or do you prefer to meet people organically?
65. What was your best first date?
66. What’s one thing you like to know about someone before you go on a date with them?
67. How do you feel about sex on the first date?
68. When was your last serious relationship?
69. Do you think you’ll ever get married?
70. What would you do if you were dating someone your friends didn’t like?
71. Have you ever cheated on a partner?
72. Have you ever been cheated on?
73. What was your hardest breakup?
74. What’s one thing you learned from your last relationship?
Questions to Get to Know Each Other Better (So You Know What You’re Working With)
75. Do you have siblings? Are you close with them?
76. Are you a morning person or a night person?
77. How would you describe your personal style?
78. Do you consider yourself an introvert or an extrovert?
79. Do you see yourself having kids someday or are you more of a cool uncle type?
80. Do you have a big friend group or a small circle of close friends?
81. Do you like to cook or are you more of a takeout person?
82. What’s one thing you miss about your hometown?
83. What was your favorite age and why?
84. What was your dream job growing up?
85. Do you like your job now?
86. What do you do to calm down when you’re stressed?
87. What was the last thing you laughed really hard over?
88. What do you do to celebrate big news?
89. If you had to move to another city tomorrow, where would you go?
90. What was the last TV show you were obsessed with?
Questions to Ask If You’ve Been Together for a Minute (Bc There’s Always More to Know!)
91. What’s one thing you’ve never told me?
92. What do you remember most about our first date?
93. What’s one way you think you’ve changed since we started dating?
94. What’s one thing you’ve never done that you want to do?
95. If you could repeat one year of your life, which one would you choose?
96. What’s one thing you wish we did more of?
97. What’s your favorite memory from the past year?
98. Where should we go on our next vacation?
99. What’s one misconception you think people have about us as a couple?
100. Where do you see us five years from now?
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