1. If you imagined yourself as any historical figure would that get you turned on for some sexual role-play later?
2. Do you have any siblings, like a younger sister, maybe?
3. You haven’t updated your profile picture in awhile, have you?
4. Does this dessert count as foreplay?
5. Is it weird that I’m still living with my ex?
6. How often do you have to shave that?
7. So…your place or my parents?
8. Can I borrow 100 bucks?
9. Why don’t we go someplace a little more quiet and secluded where no one can hear anything?
10. Are those your real breasts?
11. Do you have a favorite book you pretend to have read?
12. If you could travel into the future, would you see us in bed together?
13. How did you screw-up your last relationship?
14. Do you have a pimp or are you a free agent?
15. What is the greatest achievement of your life so far, aside from getting the opportunity to go on a date with me?
16. Are you drunk yet?
17. How would you like to join the Mile Low Club?
18. If you could change 3 things about yourself, would you start with that nose?
19. Is that spinach in your teeth?
20. If you could live anywhere in the world, would you consider it to be stalking if I moved there as well?
21. How long does it take to put on all that make-up?
22. Why don’t we fly off to Paris so I can avoid prosecution?
23. If you could have dinner with any famous person, living or dead, would you order the most expensive entrée on the menu like you did tonight?
24. Did you know my aunt has that same kind of hairstyle?
25. Who do you like to do in your free time?
26. Do you mind if I take this call from my mother?
27. Is it that time of the month?
28. Did I forget to mention my zucchini fetish?
29. Can I see you again, preferably naked?
30. Will you marry me?
For more questions to ask a girl, read 250+ Questions To Ask A Girl If You Want To Know Who She REALLY Is.