30 Questions You Should Never Ask A Man On The First Date

When Harry Met Sally - Special Edition
When Harry Met Sally – Special Edition

1. What do you want to be when you grow up?

2. Can you hold that thought while I take a selfie with my entrée?

3. Do you have any stories that don’t involve World of Warcraft?

4. If you could talk to your former self, would you convince him not to get those tattoos?

5. Do you think our waitress is pretty?

6. Would you like a breath mint?

7. What’s the craziest thing you’ve ever done to avoid having a committed relationship?

8. Do you have to clear porn sites from your search history monthly, weekly or daily?

9. Do you realize I could crush your windpipe with just this finger?

10. Can we bring over a chair for my dad, since he’s my chaperone tonight?

11. Can I take a few minutes to tell you about the advantages of selling Amway products?

12. How many women have you been sexually inadequate with?

13. Did I mention that the father of my third kid got out of prison last week?

14. Can we wrap this up?

15. Do you have any idea where I put the key to those handcuffs?

16. Would you mind giving my number to that cute roommate of yours?

17. You didn’t hear a word I just said because you were too busy staring at my tits, weren’t you?

18. Do you mind if I order a second dessert?

19. Who is your favorite actress that you like to picture naked?

20. Did you spill a whole bottle of cologne on yourself?

21. If you won a million dollars would you still be asking your dates to split the check?
22. You’d never guess I was fifteen, would you?

23. Is it all right if I record our conversation?

24. Do you think I should get this thing on my lip checked out?

25. If you could delete all of your Facebook posts that involve you and your buddies drunken antics, would there be anything left?

26. What time is your mom picking you up?

27. Do you need help reading the menu, particularly the big words?

28. Why didn’t you tell me we were supposed to dress for an 80s party?

29. Did you get that haircut as a dare?

30. Is it in yet? Thought Catalog Logo Mark

About the author

Darren Johnson

More From Thought Catalog