1. Is it too obvious that I’ve dressed up for this special occasion?
2. I’m sorry if I seem nervous. I hope I’m not freaking you out. Am I freaking you out?
3. Is it okay if I don’t eat much on this date? I just want to be my best self.
4. Have you tried to Google me?
5. Oh, you can’t find me on Google? Okay. That sucks. But have you tried searching me on Facebook? Instagram?
6. Will you believe me if I say I didn’t totally check your social media accounts on my way here?
7. Does anyone know you’re on a date right now?
8. And just in case you’ve decided you kind of like me, will you ask me to keep this relationship very secret?
9. If so, what makes you think I will be comfortable with that?
10. That must be an aggressive question. Am I starting to sound dramatic to you?
11. The weather is so perfect today. Do you ever ask someone about the weather? When you can’t think of something else to ask?
12. How long have you prepared for this date? Do you think I spent hours and hours thinking of this moment?
13. Do you easily get bored? Wait, why are you yawning?
14. Can we at least try not to touch our phones for half an hour? Am I coming across as controlling?
15. Your eyes are great. They’re like windows to your soul! Do you mind if I stare at them longer than necessary?
16. What’s your first impression of me? You don’t have to lie — it’s fine. But please don’t be rude.
17. What do you like about me so far?
18. Is it weird to be falling in love already on the first date? I mean, not saying that I am. But do you think I do though?
19. Do you feel things deeply? Immensely? Greatly?
20. Have you tried suppressing your emotions? Has it worked?
21. Are you okay talking about feelings?
22. What are your thoughts about someone who’s a chronic over-sharer? Just curious.
23. Do you stare at your ceiling before you sleep?
24. Will you think of me tonight the same way that I will? Lol. That was a joke. Moving on.
25. Do you love your job? Like really love your job? You do? How?
26. Which has a higher spot in your priority — relationship or career?
27. Has someone called you a selfish before? Did you think they were telling you the truth?
28. Are you one of those people who consider dates as job interviews?
29. Okay… so how many dates have you been on before this?
30. How many hearts did you break in the past?! Sorry, that was intense. What I mean is, how many relationships did you have in the past?
31. Do you think I won’t be offended if you ask me the same question?
32. Was there a time when someone accused you of being a narcissist?
33. What’s your point of view about the idea of forever?
34. When is the right age for you to settle down?
35. What do you mean you don’t want to settle down?
36. Am I disappointing you already at this point?
37. What would you do if I just start crying and screaming right now?
38. Have you ever heard of the word humor before?
39. Speaking of humor, do you watch romantic comedies? No? Okay. How about comedies?
40. I like to say bad words once in a while. Are you fucking okay with that?
41. Are you a bad person? Have you murdered someone? That’s a silly question. Let me rephrase. Have you thought about murdering someone?
42. Do you see a therapist, too?
43. I don’t trust people who don’t read books. Do you read books?
44. Um, that’s fine. I can make an exception for you. Do you believe in astrology? When’s your birthday?
45. If I tell you our zodiac signs are super compatible, will you agree on a second date?
46. Why do you suddenly change the subject?
47. Have you ghosted someone before? Do you think that’s a legit reason for you to be branded as an asshole?
48. You hate it when people call you an asshole? I thought you don’t have a soft side. Why do you sound so defensive?
49. Something came up? What’s the emergency? What are you leaving for?
50. Okay, nice meeting you. Can we split the bill?