Home Love & Relationship 30 Flirty Questions To Ask Your Guy Crush

30 Flirty Questions To Ask Your Guy Crush


One of the hardest parts of dating is coming up with the right words to say. You might have no problem blabbing on for hours at work or with your friends, but when your crush comes around suddenly all words fail you.

Don’t worry, it happens to the best of us. One way to fight this problem is by preparing ahead of time. That’s why we’ve prepared a list of 30 flirty questions any girl can ask their crush.

These questions are designed to set the mood and get him engaged. Pick and choose your favorite, personalize them, do whatever it takes. This isn’t meant to be a script, just inspiration.

1. What was your reaction when you first saw me?

Getting him to think about you is always a good idea. Just be careful, you might not always get the answer you want. Still, no matter the answer you get you’ve always got room to grow. With a little work and personality, it is possible to overcome a bad first impression.

2. What does it mean to be in love?

If you can get a guy thinking about love while he’s talking to you, then he’s more likely to develop feelings for you. It’s also good to get a sense of a man’s philosophy on love so you can see how you might fit into the picture.

3. What was the best date you’ve been on?

Once again, you’re getting him to think positively. You should also pay attention to his answer so you can come up with date ideas that you think you’ll like. After all, after you’re done with him, you want to be the one he thinks about when he remembers his best date.

4. What was the worst date you’ve been on?

While positive questions are good that negativity is all bad. Everyone has had bad dates, talking about his past experiences can be a good chance to bond. You will also learn what sort of things you need to avoid on future dates if you want to stay on his good side.

5. What would your dream date be?

Hopefully, your guy’s best date is still to come, and if you get him to describe his perfect date, then you can make it happen.

6. What is the longest relationship you’ve had?

This will help you know how he is with commitment. If a man has dated women for years at a time, then there’s a chance you can go the distance with him.

7. What is the shortest relationship you’ve ever had?

If he’s had any comically short relationships, you’ve got another chance to sympathize with him. Or you might learn that he has commitment issues. Whatever the case may be, an honest answer to this question will really help you.

8. When did you get out of your last serious relationship?

This will help you figure out if he’s moved on from his last girl or if he’s still hurting. There’s no hard rule, but if he just got out of a long-term relationship in the past few weeks, then you’ve got to move much more carefully.

9. What do you like best about my body?

Get him looking at your body and thinking about it. Even if he hasn’t been checking you out before this question will give him a chance to give your body a good look. If he’s attracted to you at all, he’ll jump at the chance.


10. What do you think is your best feature?

Figure out how he feels about himself. If he’s shy and self-deprecating, you can complement him. If he’s cocky, then try and tease him to show you’re not in awe of his looks, even if you are.

11. What sort of hair do you like on a woman?

Every guy has preferences. Short or long, up or down, blond or brunette. See what he likes. You know things are going well if he describes your hair.

12. Are you a boob man or a butt guy?

Every man knows what he is. Men love both, but every man loves one more than the other. Plus, once you move the conversation in a sexier direction your crush will get a sense that you wouldn’t mind your relationship moving in a sexier direction too.

13. What attracts you to a woman?

This is another chance to get a sense of what he’s looking for in a woman. You can tell a lot about a guy from the sort of things that he notices.

14. What does your ideal girl look like?

See if he describes you. It can actually be a good thing if he doesn’t just try and compliment you, honesty is a good sign. You only need to be worried if he describes someone who is nothing like you.

15. If you could go out with any girl in history, who would it be?

This question is a more creative way of getting to know his type and what he values. See if he goes for a great beauty or an important historical figure. It will give you a sense of whether he prefers beauty or brains.

16. What is your biggest turn off?

Learning this will help you decide your compatibility. You want to know if you’re turning him off now, or if you might expect to in the future.

17. Where is your favorite place to be touched?

Once you know where he likes to be touched, then you can go ahead and try to touch him there. Simple yet effective.

18. How do you not spend all day looking in the mirror?

Let him know that you think he’s sexy with this playful question.

19. What’s the most romantic gesture you’ve ever made?

This will give you a sense of whether or not he’s a romantic person. You’ll also get a sense of what he thinks is romantic, which is always helpful.

20. How are you still single?

This makes your attraction pretty clear. It also gives him a chance to admit if he is taken. Some guys will also open up about their faults, which isn’t always fun but it is always helpful.

21. Who was your first crush?

Learn more about his history and get him thinking about romance. All this in just one question.

22. How was your first kiss?

Get him thinking about kissing. It’s impossible to know the sort of answer you’ll get, first kisses can be beautiful, tragic, comedic, or some mix of all three. Whatever he says, roll with it and stay positive.

23. What would you say to a girl you wanted to seduce?

Even if he isn’t sure about his feelings toward you if you get him to act like he’s in love with you then his feelings will grow stronger.

24. What is the sexiest thing a woman could say to you?

Once again, when you know what he thinks is sexy, you can make his wish come true.

25. What is your favorite non-sexual thing to do with a woman?

Another great question to help you get closer to him. Getting a sense of what he enjoys doing and what turns him on will allow you to make all the right moves later on.

26. Do you give massages?

Give him the idea that you want his hands on your body. It’s always worth finding a guy who gives a mean massage. It’s a true sign of a keeper.

27. Do you enjoy being assertive or do you want a woman to make the first move?

This question allows you to encourage him to make a move. But even if he doesn’t, you will have room to make a move yourself. If he says he likes women who make the first move, then it’s time to start taking things to another level.

28. What would you do if I kissed you?

Tired of waiting for your crush to kiss you? You don’t need to wait anymore, ask him this question and you’ll be sure to get a kiss or at least a clearer understanding of where you stand.

29. What are you doing later?

If he hasn’t asked you out, then there’s no reason that you can’t try and grease the wheels a bit with this question. Some guys need you to be forward.

30. My place or yours?

Hey, if you know what you want then why not go for it? This question isn’t for the faint of heart, but if things have been going well then there’s a good chance he’d be down for it.


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