50 Questions to Ask a Guy You Have a Crush On

By on August 14, 2015

Crushes can be SO difficult. You never know what to say, your words come out in knots every time your crush comes around, and the nervous tension can makes things incredibly awkward. Well, ladies, listen up! I’ve come up with a handy list of 50 awesome questions to ask a guy you have a crush on- from basic to funny, interesting to juicy. You’ll find out TONS about this new cutie and you might just find out if he’s feeling the same way about you, too!

questions to ask a guy
1. One thing that can always make you smile?

Obviously a very important thing to know. With this question you can find out what makes that cute smile of his light up so you can work it in the future. You may also find out a few of his likes and interests in the process!

2. Some of your biggest interests?

Is he a sports guy? Does he love music? Knowing his interests will help you learn more about the guy you’re crushing on and also give the two of you some things to talk about. If his interests are the complete opposite of yours, you may even decide you’re better off as just friends.


3. What are you passionate about?

See how ‘deep’ your guy crush REALLY is. Is he just passionate about the soonest football game, or does he have a true passion for helping the less fortunate around the world?

questions to ask a guy

4. Favorite thing to do with your free time?

Find out a TON about what he likes to do with this question. Plus, if he mentions something like watch scary movies or read a cool book, you can suggest the two of you do it together sometime!


5. Most memorable moment of your life?

This can be quite an interesting question that is bound to have the two of you talking endlessly. You might learn a really unique story that sets this guy apart from the rest.


6. Most embarrassing?

If he’s willing to share the most embarrassing moment of his life, you can know that he’s comfortable with you and has a good personality. He’s not afraid to be silly and doesn’t mind sharing a funny story with you. Win!

questions to ask a guy

7. Favorite sport?

Because almost every guy likes sports, and this is definitely something he will want to talk about for at least 10, 20, maybe 30 minutes!

questions to ask a guy

8. Favorite food?

What’s his flavor of choice? A handy question that will definitely help in the future. Does he love burgers? Well, you just so happen to be having a barbecue this weekend and he should totally come, right!?

Favorite movie

9. Favorite movie?

Does he love the thrill of an action-packed James Bond film, or does he prefer a silly James Franco show? You can tell a lot about a guys personality by the movies he likes, and it’s another great opportunity to ask him out for a movie date.


10. Favorite band/artist?

Another easy way to learn a bit more about someone’s personality is to know their music style. Does he fancy the art of Beethoven or does he prefer the loud rockin’ sounds of Metallica?

questions to ask a guy

11. Favorite animal?

Just a cute question that everyone loves to ask!

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12. Where have you always dreamed of traveling?

A classic question that will let you in on all his exotic traveling dreams!


13. Who is your celeb crush?

An easy way to find out his type.


14. Favorite feature on the opposite sex?

An important thing to know when you’re trying to reel a guy in.


15.  Something that annoys you?

Find out the one thing you should probably NEVER do.


16. Any nicknames?

He may have a super adorable and silly nickname that you can playfully tease him with about for years.


17. What does your future look like in your eyes?

You should always know how your potential partners future looks.

bad habits

18. Your worst habit?

Why WOULDN’T you want to know their worst habit? This could be a potential deal breaker!


19. Biggest thing you’re attracted to (aside from looks)?

Another very important question to see if you fit his mold.


20 .Are you a player?

If he says yes, lose the crush right now!


21. Looking for a relationship?

If he says no, then you should probably move on. If he says yes, I’d keep flirting with him until you can’t flirt any more!


22. Longest relationship?

If he’s never been in an actual relationship that lasted several months or years, it may be a sign he’s immature or not ready for anything serious. In that case, run for the hills!

questions to ask a guy

23. Reason your last relationship failed?

An important question- after all, what if it failed because he cheated? That’s something you’d want to know before you consider a relationship with this guy!


24. Craziest dream you’ve ever had?

A fun question that could certainly leave you shocked or laughing your head off.


25. Ever want kids?

If you want kids and he is adamant against ever having any, you might want to reconsider your crush.


26. Rather party or do something quiet?

A party animal type of guy might not be looking for a solid girlfriend or long-lasting relationship, while someone who is quiet will probably prefer a special someone in his life.


27. Dream date?

See what kind of guy he is and what potential date the two of you might go on one day.


28. Go on an adventure or keep it casual?

An easy way to find out whether or not your crush is a thrill seeker or someone who plays it cool.


29. Religious?

Again, this is an important question to find out before you enter into a relationship. Having different religious views could potentially ruin your partnership, so knowing whether or not you’re on the same page is a must.

 questions to ask a guy

30. Last concert you attended?

Find out just how often your crush likes to go out and listen to some tunes!


31. Pay more attention to looks or personality?

Is your crush the shallow type that only cares about looks, or is he looking for a connection that is much deeper than physical? This is obviously something you will want to know right off the bat.

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32. Biggest regret?

Whether it’s big or small, if he is willing to share his biggest regret with you, it definitely says something about your guys’ relationship. You may be surprised what his biggest regret is, but hey, remember- HE REGRETS IT, so try not to hold it against him.


33. Believe in giving second chances?

Some people are totally against giving second chances while others will happily give seconds or thirds depending on the situation. A wonderful conversation starter!


34. How your friends would describe you?

We all see ourselves a certain way, but our friends see us from a different point of you, and therefore probably have some different things to say about us. Well, what does your crush’s guy pals have to say about him? You might hear some interesting things with this particular question!


35. Fictional character that represents you closest?

Again, you can find out a TON about the person he is and how his personality is with this simple question. Does he see himself as a superhero, or a con artist? Is he a villain, a doctor, a comedian? The list goes on and on and the possibilities are really endless.

 questions to ask a guy

36. Biggest weakness?

Everyone has a weakness- and if your man crush is able to admit where he is weak, that tells a lot about his confidence and personality. Who knows what makes him weak!?

37. Dream career?

A classic question that’s always a hit. He might have a really random and totally out-of-this-world answer, or he might keep it basic like doctor or singer.


38. How do you handle people you don’t like?

This is a great question to find out his temper levels. If his answer sounds something like ‘I scream and yell at people’ or ‘I tell people off often’, you can probably guess he’s a bit of a hothead. On the other hand, if he chooses to ignore or walk away from people he doesn’t like, it shows he is level headed and can handle his emotions.


39. How would you describe me?

Because I’m sure you’re DYING to know what your crush has to say about you, right? Get him to open up a little bit with this easy question. It’s not too deep or prying, yet still makes him say a few words about YOU!

 questions to ask a guy-11

40. Do you like me?

This is a really bold and daring question- definitely not for the faint of heart. He might surprise you and come out with a ‘yes’, or he might beat around the bush, afraid to tell you the answer. Either way, it’s a fun and out there question that will catch him off guard. I wonder how he will respond to you?

41. Funniest thing you’ve ever said/done?

Because every girl loves a man with a good personality, who isn’t afraid to be funny and silly every once and awhile. Make him tell you a funny quote or story. If he makes you legitimately laugh, that’s bonus points for this crush!


42. Morning person or night owl?

If you’re an up-with-the-sun waker and he prefers to fall asleep around 5AM, you might not want to invite him out for morning brunch. Trust me, this is something you will want to know for the future!


43. Greatest fear?

Everyone has fears, but very few men are able to admit it. Find out what makes your potential man frightened or scared and see a softer side of your crush.

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44. What am I thinking right now?

This is a really fun and silly question, and there is NO telling what the answer will be! He could come up with something totally random and ridiculous, or maybe something flirty and cute. Definitely give this question a try, especially when the conversation seems to be slowing down; it’ll pick the convo RIGHT back up.


45. Would you ever date me?

Because this is OBVIOUSLY something you should know. If he says anything but ‘yes’, I would drop the crush real quick and find someone else who is actually interested.

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46. Would you like to go on a date with me?

If he says yes to the first question, then there’s really no better time to actually ask him on a date. And ladies, there’s absolutely nothing wrong with asking a guy out- they get shy just like we do, and a lot of men like a lady who isn’t afraid to make the first move.

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47. Nickname you’d give me?

A cute question that always ends in smiles and giggles. I wonder what cute nickname he will end up giving you?


48. Ever cheated?

You know what they say, once a cheater, always a cheater. And although there’s a small percentage of those who are a one time offender, if he’s cheated on a past girlfriend and doesn’t have an amazing story or excuse to follow, I’d consider a new crush.


49. Close with your family?

Is he a family oriented guy or not? This is certainly an important question that will let you know more about his personality and his past.

 questions to ask a guy

50. Do you ever want to get married?

This is much like the kid and religion question. If he says no, and you are 100 percent sure you want to get married, you’re probably not going to change your mind. Either accept that you probably won’t ever have your dream wedding or move on. Being on the same page is incredibly important, especially when it comes to things like this!


See? Talking to your crush doesn’t have to be a heart-stopping event. Ditch the shyness and awkward tension and pick some of these totally fun and awesome question to ask your guy crush- all of which will give you plenty of insight on this potential man of your dreams!


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