55 Truth Or Drink Questions To Ask Your Boyfriend Tonight Over A Bottle Of Wine

Either answer the question honestly or take a sip from your wine glass (or even better, do a shot).

Twenty20, kirstylee
Twenty20, kirstylee

1. Did you masturbate to the thought of me before we met?

2. Do you think I’m the person you’re going to marry?

3. Have you ever faked an orgasm with me?

4. Have I given you the best sex you’ve ever had?

5. When did you realize that you were in love with me?

6. What went through your mind when you first saw me?

7. What do I do to turn you on without realizing it?

8. What fetish do you have that I don’t know about yet?

9. If you could change one thing about our sex life, what would it be?

10. What does your mom really think of me?

11. Did I ever buy you a gift that you pretended to like, but actually hated?

12. Who was the last person you had a sex dream about?

13. Where was the craziest place you’ve ever had sex with someone else?

14. When was the last time you watched porn?

15. Are you horny right now?

16. How many sex toys do you own?

17. Do you think I’m more attractive now or when we first met?

18. If we break up, do you think you’ll be the one getting dumped or that I’ll be?

19. If you were offered a ton of cash, would you do a porno?

20. What was the last lie you told me?

21. What annoying thing do I do that you can’t stand?

22. Have you ever thought about breaking up with me?

23. When was the last time you spoke to your ex?

24. What’s the longest period of time you’ve gone without getting laid?

25. Did you ever suspect that I was cheating on you?

26. When was the last time someone hit on you?

27. Have you ever had a one-night stand?

28. How old were you when you masturbated for the first time?

29. Would you have a threesome with me and one of your guy friends?

30. Have you ever used a dating website before?

31. Do you actually like my friends?

32. How many people have you slept with?

33. How many people have you kissed?

34. Have you ever thought about someone else during sex with me?

35. Do you like my cooking or your mother’s cooking better?

36. Would you let me read through all of your text messages if I asked to see your phone right now?

37. Do you love your pet more than you love me?

38. Am I the “type” you usually go after?

39. Have you ever sent someone else a dick pic?

40. Do you enjoy going down on me?

41. Which one of my friends would you sleep with if we weren’t dating?

42. Are you happy with our sex life?

43. If you could sleep with any celebrity, who would you choose?

44. When was the last time you masturbated?

45. Have you ever had an STD?

46. What do I do during sex that you don’t actually enjoy?

47. What should I do more of during sex?

48. Have you ever been to a strip club?

49. Do you like the way I dress?

50. What song reminds you of another girl?

51. Do you wish my boobs were bigger?

52. Am I good at giving blowjobs?

53. Do you think I’m out of your league or you’re out of my league?

54. What website do you use to watch porn?

55. If we got married, what would your vows be? Thought Catalog Logo Mark

More From Thought Catalog