55 Things I Wish I Could Ask The Guy I Almost Dated 

55 Things I Wish I Could Ask The Guy I Almost Dated 

1. How did you feel about me?

2. Did you ever plan on dating me?

3. Were you texting other girls at the same time you were texting me?

4. Were you lying when you told me how much you liked me?

5. Was the chemistry I felt actually one-sided?

6. Did I read the situation completely wrong?

7. Why did you keep hitting on me if you weren’t going to ask me out?

8. Did someone hurt you in the past?

9. Were you afraid of getting into a relationships, afraid of how much you liked me?

10. Or was the problem that I liked you much more than you liked me?

11Did I do something wrong?

12. Did you find someone better?

13. Was everything that happened between us a lie?

14. Or did you value our friendship?

15. Looking back, did our conversations mean as much to you as they did to me?

16. Did you get excited when you saw my name pop onto your phone?

17. Did you ever picture a future where we were boyfriend and girlfriend?

18. Or did you know I was only a temporary part of your life from the start?

19. Did you know you were leading me on?

20. Did you know you were sending mixed signals?

21. Why did you waste your time with me if you didn’t feel the same?

22. Did you want to sleep with me?

23. Did you get your ego boosted from all my attention?

24. Did you like the idea of me more than you liked the actual me?

25. What were you thinking when you stared into my eyes?

26. Did you mean it when you told me you cared?

27. Or were you only telling me what I wanted to hear?

28. Did you think you were out of my league?

29. Did you think I was out of your league?

30. Did I push you away on accident?

31. Was there something more I could have done to keep you around?

32. Are we both to blame?

33. Or was it just bad timing?

34. Was it just bad luck?

35. Now that I’m gone, do your friends ever ask about me?

36. Did your friends even know about me?

37. Are there songs that make you think of me?

38. What about movies, shows, books?

39.  What is your first thought when you see my posts on social media?

40. Do you ever check to see if I looked at your posts?

41. Do you wish we could have stayed friends after everything that happened between us?

42. Or are you relieved you never have to see me again?

43. Do I ever come up in conversations?

44. Have you told your new girlfriend about me?

45. Is she jealous of me?

46. Does she know the story, does she know why we didn’t work out?

47. Why didn’t we work out?

48. Do you realize how much it hurt me when you walked away?

49. Do you feel guilty about what you put me through?

50.  Are you ever tempted to text me?

51. Do you ever think about me?

52. Do you consider me the one who got away?

53. Or do you consider me another one of your mistakes?

54. Do you wish things ended differently between us?

55. Do you miss me? Thought Catalog Logo Mark

January Nelson is a writer, editor, and dreamer. She writes about astrology, games, love, relationships, and entertainment. January graduated with an English and Literature degree from Columbia University.