25 Questions We Don’t Ask Each Other Enough
1. “Do you actually want to be going to this party/bar/club, or are you just doing it because you feel obligated to?”
2. “Is this person you’re dating — this person I might like for any number of arbitrary reasons — treating you well? Because that’s all that actually matters.”
3. “I know that we usually try to sweep that stuff under the rug socially, but I think we’re all pretty stressed about loans and jobs and stuff. Do you want to talk about money?”
4. “What is your favorite memory from when you were a little kid?”
5. “What is the time you felt most alone as a little kid?”
6. “If you had to make a list of things you want to accomplish in your life, what are some of the top items? Do you feel like you’re going to get to them?”
7. “Do you like the things we all do together as friends, or do you feel like the stuff you want to do never makes it onto the agenda?”
8. “Do you need any help with that?” (This, it should be noted, is just as important to strangers carrying a lot of groceries as it is with friends who are going through a rough time.)
9. “Are you lost?” (To people who are clearly lost and trying not to freak out about it in front of the subway map.)
10. “If you don’t want to talk about it, you don’t have to, but are you okay since your breakup? I noticed that you’ve been really down, is there anything I can do?”
11. “Do you just need to be alone for a little while?”
12. “What movie do you want to go see tonight?”
13. “Do you know that it’s not your fault if you’re having a hard time finding a good job? You shouldn’t be beating yourself up even further.”
14. “Do you know that I love you? I mean, really, do you know that you’re loved and cared for?”
15. “If you could change one thing about yourself, what would you change and why?”
16. “What is something that you like to do in your spare time — even if you’re not really good at it?”
17. “What is the thing that other people do that upsets or frustrates you the most? Something that they might not even realize that they’re doing?”
18. “Do you feel more comfortable when you’re alone, or with other people? Why?”
19. “Do you look at yourself in the mirror often? Do you have an angle that you prefer to look at, in pictures and in your own reflection?”
20. “What are some of the things that people have said about you that you still think about to this day?”
21. “What do you hope that people say about you the most?”
22. “How is your day going?” (To the people throughout our day — from cashiers to people we always see on our commutes — that we tend to ignore or dismiss with a half-hearted hand wave.)
23. “What is your favorite part of the day?”
24. “Do you feel like you are really loved, or that the people in your life really listen to you when you talk?”
25. “What are you most afraid of?” 
