Are you going to pay for this date, or should I have my wallet ready?
Admit it, dating is HARD.
1. Why are you single?
2. What is your genuine first impression of me?
3. Is there anything you dislike about me already?
4. Are you emotionally unavailable?
5. Do you have commitment issues?
6. If we end up dating, will either one of us be settling?
7. What’s your biggest insecurity?
8. How will you react if I keep my guard up with you (for a little while, at least)?
9. Have you ever cheated on someone?
10. Have you already lurked on my internet presence?
11. How freaked would you be if I told you I already looked you up online?
12. Are you looking for something serious or casual?
13. Are you going to kiss me or will I eventually have to make the first move?
14. Have you ghosted on people in the past?
15. How many times?
16. Who did you vote for in the last election?
17. You didn’t vote?
18. Why didn’t you vote?
19. Do you want to get married someday?
20. If so, what do you think about pre-nuptial agreements?
21. Do you plan on having kids, or do you want a life without any?
22. Are you thinking about making any major residential moves in the next few years?
23. Do you always need to be right about everything (and let people *know* you think you’re right)?
24. How old were you when you started having sex?
25. What’s your weirdest and/or darkest sexual fantasy?
26. What’s your preferred method of birth control?
27. Have you ever been tested?
28. When was the last time you got tested?
29. What turns you on the most?
30. What’s your biggest fear in life?
31. What’s your least favorite thing about yourself?
32. What have other people you’ve dated liked the most about you?
33. What have other people you’ve dated complained about the most?
34. Have you ever struggled with any mental health issues?
35. How do you honestly feel about dating someone who has mental health issues of their own?
36. Have you ever been arrested?
37. Why did you break up with your last significant other?
38. Why did your last significant other break up with you?
39. How long did you date for?
40. Do you still love them?
41. Have you ever been in love in the first place?
42. Are you pro-choice?
43. What’s the worst date you’ve ever been on?
44. Has anyone close to you ever died?
45. How do you cope with death and grief?
46. Where do you see yourself in five years?
47. Have you ever been in a serious relationship before?
48. Why/why not?
49. What’s the longest amount of time you’ve gone without being in a relationship?
50. Are you friends with all of your exes on Facebook?
51. How frequently do you check your ex’s social media accounts?
52. Do you still talk to them on the phone?
53. Is it out of the ordinary for them to like your Facebook statuses and vice versa?
54. Tell me everything about your drinking and drug habits.
55. What memories have scarred you for life?
56. How close are you to your siblings?
57. What’s your relationship like with your parents?
58. If I ever meet your parents, are they going to be nice to me?
59. Do you call your mother without prompting?
60. Are you dating because you want to find love or because you’re just afraid of being alone?
61. If you could change anything about your personality, what would it be?
62. Are you going to pay for this date, or should I have my wallet ready?
63. Are you just going to sleep with me and never call me again?
64. Do you actually see yourself liking me?
65. How do you think this is going so far?