25 Questions to Ask a Guy You Like

A girl who used these questions to ask a guy you like, laughing with her boyfriend as they take a photo in front of a waterfall.

Asking questions is the easiest way to get to know someone. It shows that you’re thoughtful and that you’re interested in learning more about them. But thinking of questions to ask a guy you like can also be intimidating. What should you ask? What shouldn’t you ask? Should you try to be funny?

If you’re not sure which questions to ask a guy you like, don’t panic. We have 25 tried and true questions that guys will actually enjoy answering. Some are silly and some are serious, but all of them will help you get to know your crush better—and help him get to know you, too. Plus, they’ll show him that you’re thoughtful. Win-win.

Pro tip: Don’t fire these questions off one after another. You don’t want to go through them all at once! Remember, it’s a conversation, not an interrogation. You want to come off as thoughtful and interested, but you don’t want to always be the one doing the asking.

The next time you need a conversation starter or want to keep the flow going, just remember these and you’ll have a smooth ride.


Try these questions to ask a guy you like…

1. How would you describe yourself in five words?

2. How would you describe your perfect girl in five words?

3. What’s the one accomplishment you’re most proud of?

4. What’s your biggest pet peeve?

5. What were your childhood nicknames?

6 . What, in your opinion, is your best quality?

7. What never fails to make you laugh?

8. What’s the best compliment you’ve ever received?

9. Do you think your zodiac sign accurately describes you?

10. If you could choose one superpower, what would it be?

11. What’s your favorite fast food place?

12. Do you believe in ghosts?

13. What was your first cell phone?

14. If you ever got a tattoo (or if you already have one and get another one), what would you get?

15. If you could only watch one TV show for the rest of your life, what would it be?

16. Do you have any hidden talents?

17. What’s your favorite part about your job?

18. How do you like to spend your weekends?

19. What does your perfect Saturday night consist of?

20. Are you an early bird, or a night owl?

21. Who inspires you the most?

22. Do you have a favorite quote or mantra?

23. What do you think happens when you die?

24. What’s the nicest thing someone has ever done for you?

25. What do you like most about me?

Think of these questions to ask a guy you like as lifelines when you need something to say. Chances are, each question will lead you to entirely new questions and conversations that aren’t even on this list. And remember: As important as asking questions is, it’s equally as important to listen to your crush’s responses. Happy chatting!

Elizabeth Entenman

Freelance Writer

Elizabeth is a freelance writer, editor, and advertising copywriter in Brooklyn. Right now, she’s probably somewhere Instagramming her dogs.

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