1. What’s your policy regarding leaving people suddenly and without warning?

2. I’m not saying right away, but eventually down the line, how open would you be to introducing a third party to our sex life?

3. Do you floss?

4. Are you obnoxiously dependent, or are we still going to be able to have our own lives?

5. Are you going to make me wait 6 dates before sleeping with me?

6. Is it okay if we wait like, 6 dates before sleeping together?

7. Do you actually watch Rachel Maddow/Read the NY Times/love this band/go to MoMA in your spare time, or are you just saying that?

8. What were your SAT scores?

9. If we were to date, how often would you expect oral sex? Like, is this a regular thing, or a once in a while treat?

10. How much money do you actually make?

11. If we go home together tonight, I’m not really going to want to cuddle. That cool with you?

12. Are you seeing other people? HOW many other people?

13. You talk to your ex how often?

14. What’s your number? (Not your phone number. The other one.) Just give me a ballpark range.

15. Will you be willing to take a backseat to my career? Will you want me to take a backseat to yours?

16. Will you be just as apt to keep the bathroom door closed six months, six years into the relationship, as you are right now?

17. Do you have any plans to gain a ton of weight/lose a ton of weight/take up drugs/change your career/change your religion/change your country of residence, or in any other way drastically alter your life in the next two years?

18. Will you always expect me to pay? (Will you always pay?)

19. Does any part of you right now think that I’m not someone you could be serious about? How attracted/interested in me are you really?

20. Wait, is this a date?

Originally published in May 2020.