20 Questions to Ask Your Crush

By on December 5, 2013

Having a crush on someone is already hard enough. But when you don’t even know what to talk about with your potential boyfriend, the whole situation becomes even more stressful. Try out these 20 questions that will break the ice and help you get to know them better.


1. Are you seeing anyone?

This should always be the first question. If the answer is ‘yes’, then you clearly don’t need to continue with the following questions. Either move on, or take a risk and see if the current relationship fails.

2. What do you look for in a woman?

This question helps you to determine if you two are even compatible. Just remember: if you’re not his type, don’t change yourself just to please him.


3. How long was your longest relationship?

If his longest relationship was only 3 weeks, it may mean that he’s not looking for anything serious. On the other hand, if he’s been involved with someone for several years, it could mean that he’s a romantic man looking for love.

4. What is your worst habit?

An important question because it could potentially be a deal-breaker. For example, if his worst habit is smoking cigarettes and your an avid non-smoker, you might realize he’s not the one for you.

5. Who’s your celebrity crush?

Finding out his celebrity crush can give you an idea on what kind of woman he’s after.

6. What is your favorite television show of all time?

With this question you can find out a bit of his personality. A guy who loves television shows with plenty of action might be a tough guy, while a man obsessed with comedies might have a funny and cute personality.


7. Would you rather have unlimited love or unlimited money?

If he answers ‘money’, you might be dealing with a materialistic man who cares more about goods than his partner. On the other hand, a guy that picks unlimited love shows he is extremely caring and truly looking for his soulmate.

8. Snowboarding or surfing?

Finding out whether he’s a rugged snowboarder who fights against the snow-topped mountain peaks or a relaxed surfer gliding along the waves can really give you an idea about his personality type.

9. What’s your favorite genre of movies?

Another great way to find out more about his personality is to find out what genre of movies he enjoys. As an added bonus you’ll be able to know which movie the two of you can see together on a first date!

10. What’s the most embarrassing thing that’s happened to you?

Not only will this get a good laugh, but you’ll be able to see a different side of him: if he doesn’t share, he may be unconfident or simply mysterious. If he does share, he might be a joker who loves to mess around.

11. What is your weirdest deal-breaker?

Finding out what is an automatic deal-breaker for your potential man is just something you need to know to see your compatibility and also refrain from doing whatever it is his deal-breaker is.

12. What is your idea of a dream date?

With this question you can find out exactly what type of boyfriend he is: a romanticizer or a bore-fest.


13. What do you like about yourself the most?

See how confident he is in his own skin.

14. Does he think you’re cute?

This question might be a bit out there and upfront, but there’s no better way to see if someone is interested in you than to be completely honest. If he says yes, you’re in the running for next girlfriend!

15. Have you ever been in love?

If he says yes, than he will know a thing or two about romance. If he says no, he might be a bit immature when it comes to the love game. But you can change that, of course.


16. What is your biggest fear?

Find out whether he’s a total pansy afraid of butterflies or if his fears are much greater and deeper than anything you’d thought possible.

17. What is your favorite food?

Here you will find out if he is the adventurous type, diving into the realms of hot spices or whether he’s an all American man who enjoys a pizza and a beer.

18. What is your favorite color?

Colors can actually tell a lot about a person. If he chooses a subtle color like green or blue, he may be more relaxed while someone who chooses red may have a hot temper.

19. Why did your last relationship fail?

This particular question may be a bit too personal for some, but if he chooses to answer it can tell you a lot about his dating habits.


20. Is he interested in you?

Another straight-forward question that will let you know right there and then if he’s interested. If you feel like taking a risk and don’t want to wonder about the potential of you two dating, be upfront and ask him if he’s interested.

Image credit: Danique, bilge, thelle548