21 Questions to Ask a Guy - Fun Relationship Questions to Get to Know Someone

Will Wright
Is it possible to get to know a guy by asking just 21 questions? While there's no magic power in the number 21, the more questions you ask a guy, the more you know about him. Sounds simple enough. But remember the 21 questions to ask a guy that you pick also say a lot about you. If you ask 21 questions about his ex, a guy will pick up pretty quickly that you may have an issue there. Likewise, if you ask 21 questions about a guy's job, that reveals a lot about you as well.

With that in mind, here are 21 questions to ask a guy that cover a broad range of relationship topics to help you get to know that special guy just a little bit better. The list is divided into three sections

Please note that these aren't 21 standard get to know someone questions, but rather fun alternatives to old standby questions like, "what's your favorite color" or "what's your sign?"

21 Questions to Ask a Guy - General Questions

Some questions to ask when you are just meeting a guy.

1. What was your favorite Halloween costume and why?

2. If you could have dinner with any three people from any time, fictional or non-fictional, who would they be and why?

3. If you could be invisible, where would you go and what would you do?

4. If your life was turned into a movie, what actor would play you?

5. What made you laugh the hardest in your entire life?

6. What's your favorite childhood memory?

7. If you were a waiter and a customer was being rude, would you spit in their food?

21 Questions to Ask a Guy - More Intimate Questions

Some questions to ask once you know a guy a bit better.

8. What is your deepest regret?

9. Have you ever dated someone from another race? Would you?

10. What was your first date like?

11. What's the worst lie you ever told? Did you get caught?

12. If you suddenly found yourself turned into a woman, how would you spend your day?

13. How do you handle people you don't like?

14. Would you rather be smart and ugly or dumb and beautiful?

21 Questions to Ask a Guy - Sexually Intimate Questions

Lay these questions on a guy when you know him well.

15. Do you have a sexual fantasy no one else knows about?

16. What's the difference between sex and making love?

17. If you could change the age at which you lost your virginity, would you? Would it be younger or older and why?

18. What's the craziest place you ever had sex?

19. Have you ever had sex with someone when you didn't really want to?

20. What turns you on? Turns you off?

21. Have you ever cheated on your partner? Did this person ever find out, and if so, what happened?

More Questions to Ask a Guy

21 Questions not enough?

To find more fun random questions to ask a guy, click HERE.

Published by Will Wright

I'm a film industry veteran with over a hundred professional credits.  View profile

  • 21 questions to ask a guy don't have to sound like a job interview.
  • Be prepared to respond if he asks you to asnwer your own question.
  • 21 Questions is a fun way to get to know someone.
You can add your own questions to the list in the comments section at the bottom of the page.

73 Comments

Post a Comment
  • Boyfriend Girlfriend4/16/2011

    Fun game! Wish there were more than 21 tho.

  • lou4/12/2011

    I've played this game with my suitor and we found it quite interesting, though we argued on our 10th question,that we weren't able to finish it til the 21st. I just hope that we'd get to finish it though...

  • 21 lover4/9/2011

    these are great questions to ask a guy! I'm gonna try these on my bf

  • Wills2/6/2011

    seriously!!! would u ever a guy these, i wouldn't !!

  • Effi L. Donovan1/31/2011

    Well! Tad bit of heat just on this page. I enjoyed your questions, particularly 5 and 13. Have you considered answering any of them?

  • The Best friend1/31/2011

    Questions are complete crap. I gotta here my friend talk about how one of your questions got them in a argument ....

  • Esmeralda Escoto1/29/2011

    Some of these questions are pretty gay.. But some are pretty creative

  • None Of Your Business1/20/2011

    They Were Okay But I Think U Should Add Some More

  • Your Mom1/16/2011

    WOW THESE SUCK ASS!!!

  • Pooka1/4/2011

    Jason is a baby That can't answer simple little questions. (:

Displaying Comments
Next »

To comment, please sign in to your Yahoo! account, or sign up for a new account.