Keeping the conversation fun and flirty is a very good idea for your first date. If you're not sure how to approach it, try 20 fun questions to ask a guy on a date.
Let him know you have a sense of humor and you're fun, but make sure you're reading the situation right. Most guys will love these random fun questions to ask a guy, but more serious ones might take them the wrong way. Pick your favorite fun flirty questions to ask a guy and make your date memorable, while learning about their sense of humor and their personality.
1. If you were a car, what kind of car would you be?
2. What actor would play you in a movie about your life? (If he goes for some of the hottest celebrities like Zac Efron or Ryan Gosling, follow it up with: "OK, but who would really play you?" while treating him to your flirty smile).
3. What do you think women like about you the most and the least?
4. If you could choose one superpower you'd have for the rest of your life, what would it be?
5. If you could travel back in time and meet yourself as a child, what advice would you give yourself?
6. What would you take with you on a desert island? A guy with great survival skills or a Playboy model?
7. If you accidentally walked in on while taking a shower, where would your eyes go to first?
8. Would you make out with your best gay friend if that would lead to the entire world being saved from certain destruction?
9. What would you do if you were swimming and lost your trunks?
10. Do you believe in love at first sight?
11. What's the one sex toy I could never convince you to use?
12. Who's your biggest celebrity crush?
13. How would you define a sexy woman?
14. What's the boldest thing you’ve done through texting?
15. Were you ever caught while having sex or masturbating?
16. What's the one place in the world where you'd enjoy having sex the most with the right girl?
17. What's the sexiest thing a woman's ever done to you to turn you on?
18. Do you have a nickname for... it? What is it?
19. What was the best party you ever went to?
20. If we had a kid together, what would you like him to get from you, personality wise?
If you see that more daring questions are not getting a good reaction for him, keep it light. The best fun questions to ask guys are allowed to make them blush, but never groan. Don't worry if you don't get to all of the 20 fun questions to ask a guy on your first date. Any of them can start a conversation on an even more interesting tangent.