Crush and dating questions

Confessions, near-misses and bad first dates. Sweet and awkward, nothing explicit.

1. What is the most awkward thing that has happened when the bill arrived?
2. Would you rather have an admirer you never identify, or identify one whose feelings already faded?
3. Never have I ever changed my train or bus route just to cross paths with one person.
4. Sing eight seconds of a love song, eyes closed, as badly as you possibly can.
5. Are you a double texter or a waiter? Be honest about your personal record.
6. Would you rather sit through an awful film with good company, or a masterpiece completely alone?
7. Never have I ever reread an old chat from the very beginning at two in the morning.
8. Write your dating profile bio in ten words and read it to the group.
9. What's the dumbest thing you've done to get a crush's attention?
10. Would you rather remember every date in perfect detail, or remember only how each one felt?
11. Never have I ever chosen a class or a club because of one specific person.
12. Describe the last three pictures in your camera roll as if they were dating app photos.
13. Which hobby did you fake being into just so you'd have something to talk about?
14. Would you rather go on a double date with your parents, or with your boss?
15. Never have I ever engineered where I stood in a group photo to end up beside one person.
16. Invent the most believable excuse for cancelling a date, right now, no thinking time.
17. Who was your very first crush, and what exactly made you fall for them?
18. Would you rather date somebody two hours away, or somebody living in the same building?
19. Never have I ever picked up a hobby purely because one person was into it.
20. Improvise four lines of a break-up ballad about losing your phone charger.
21. Have your friends ever tried to set you up? How badly did that go?
22. Would you rather get instant one-word replies, or thoughtful ones that arrive a day late?
23. Never have I ever spent over an hour choosing clothes for a first meeting.
24. Confess your undying love to the nearest inanimate object. Full sincerity, no laughing.
25. Which gift did you hand over that landed completely wrong?
26. Would you rather walk around a school festival together, or watch fireworks side by side?
27. Never have I ever changed my profile picture hoping one specific person would notice.
28. Open the last photo you took and caption it like the climax of a confession scene.
29. Describe your ideal first date in enough detail that we could book it for you.
30. Would you rather cook dinner at home for a date, or be taken somewhere very expensive?