1. How long will i last?
  2. Does she squirt?
  3. Should i "accidentally" put in her butt?
  4. Is there going to be truffle butter?
  5. Will my dick hit her stomach?
  6. Is she on birth control?
  7. If i cum inside her, will she keep the kid?
  8. What if i become a father?
  9. Should i jizz in her eye?
  10. Doggy, cowgirl, or missionary? Or none of the above?
  11. What if she sticks her finger in my butt?
  12. Does she have herpes?
  13. Do fire and ice condoms make your dick burn?
  14. Has she gone black?
  15. Should i 50 shades of grey her ass?
  16. Can i just get a blumpkin?
  17. Will she bite my dick while giving head?
  18. Does she really love me?
    Suggested by @champagnepapi
  19. Does she have a personal history that convolutes her ideas of sex and of trust that prevents her from making the best decisions for herself?
    Suggested by @champagnepapi
  20. I hope I don't cry again
    Suggested by @champagnepapi
  21. Will she like my parents?
    The connection between your significant other and the people that raised you is important. Their chemistry is as important as your own.
    Suggested by @kevinhannigan
  22. Paper or plastic?
    I don't want to be sleeping around with someone who doesn't respect the environment. She probably won't respect me. Maybe I should take her out for ice cream after!
    Suggested by @kevinhannigan
  23. Why is everybody mean to me at work?
    I come in every day with a positive attitude, keep my head down, and work my ass off just to get ridiculed endlessly. For what? A shiny new car, a 401k and a garage that's attached to my house?
    Suggested by @callahan