Best Flirty Questions to Ask a Guy

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So you just met a guy. But how do you know if he’s THE guy? You’re going to need a lot more than just looking at him to decide whether you like him or not. Lucky for you, we have the solution to your dilemma.

Every girl should be armed with interesting and flirty questions to ask a guy on any occasion. It’s the easiest way to strike up a conversation and have it last for hours on end. Keep him coming back for more with these exciting topics. 

Top 20 Flirty Questions to Ask a Guy

There’s absolutely nothing wrong with showing him that you’re interested. However, there undoubtedly is an art to it. These flirty questions are funny, engaging, random, personal, and deep. With such a mix, you’ll always be prepared. 

Read the room! Make sure you don’t get too personal too soon. You don’t want to come off as an intense girl. The main goal of this is to have fun, so keep it light and simple. As your relationship evolves, you’ll be able to squeeze in the heavy artillery.

Ask Away!

Did you just bump into a nice guy while grabbing your morning coffee? Are you already out on your first few dates? No problem! These topics won’t leave any room for the dreaded awkward silence.

     1. What would a date with you look like?

A question like this will make him picture a fun rendezvous with you. You’ll also get to know what he likes to do on dates. Find out whether he’s a dinner-and-a-movie kind of guy or if he goes all in to make dates romantic.

     2. What do you wear to bed?

This sexy question will keep the conversation steamy. Shirt and boxers? Top off? Either way, let your imagination run wild. The good news is he’ll be picturing you in bed with him, and what you’ll be wearing, too.

     3. What’s one romantic movie you’d recommend?

Movies are a great way to get to know a guy a little better. Find out what his version of romance looks like, and you’ll be able to see if it aligns with yours. You might even score an invite to movie night with him.

     4. Do you work out?

This question is pretty straightforward. You’re indirectly complimenting him on his physique, and he will love it. Guys appreciate when girls notice the effort they put into looking good. If he tells you that he doesn’t work out, he’ll still feel good about his body. Either way, he’ll feel happy.

     5. What does an impromptu weekend away with you look like?

Spontaneity goes a long way in relationships. This flirty question will make a guy imagine the two of you just packing a bag and driving off. Fancy going on a romantic weekend getaway to spend some time together? You guys might end up doing exactly that!

     6. What would you say is the best dish you’ve ever cooked?

Who doesn’t love a guy who cooks? If he does wonders in the kitchen, then he’ll be able to show off his skills. Perhaps it’ll inspire him to make a meal for you right after. If all he’s ever fixed himself is a sandwich, you’ll both still have a good laugh about it.

     7. What does your morning routine look like?

This flirty question is a great way to get to know him. Morning routines can really help you figure him out. You’ll see if he is serious about going after his dreams, or if he’s a take-it-as-it-comes kind of guy. He’ll possibly even picture waking up with you!

     8. Are you ticklish?

This tried-and-tested question is a must-ask to kick things up a notch. It will make both of you want to tickle each other. You’ll end up laughing like two crazy people who have lost their marbles. Since guys find girls who laugh inevitably sexy, this question is a no brainer!

     9. If you could drop everything right now and go anywhere in the world, where would it be?

This question will get him to talk about himself. You’ll find out what places he likes best and what he loves about them? Ask this to a guy that has done a fair bit of traveling, and you’ll really hit the spot.

     10. What’s the craziest thing you’ve done?

Get to know him even deeper. Find out how crazy he is. He’ll have a great time telling you about his loopy antics, too. If he’s as bananas as you are, you’ll know that he’s a keeper!

     11. What is something that your guy friends don’t know about yourself?

What does he talk about when he’s alone with his pals? Sports? Video games? Guys don’t really get down and dirty when it comes to getting to know one another. This question will make him see you as someone he can tell his more personal stuff to.

     12. What kind of life do you envision after marriage?

This topic might make some guys take a step back and think, “Whoa. Is she thinking about marriage already?” However, other guys (who don’t rush into conclusions) will gladly share. Learn whether he prefers the suburbs or the city, or how many kids he’s aiming for. Either way, you’ll find out what you’re getting yourself into.

     13. What do you think of girls that make the first move?

This is a great flirty question to get him thinking of you making the first move. Guys love it when girls take control. When they don’t sit back and just wait for things to happen. Indirectly, that’s exactly what you’re doing. For all you know, maybe this will push him to make the first move himself.

     14. Can you help me with… ?

Ask him if he could help you with some chores. Pick something simple, like moving a couch, driving you somewhere, or picking out furniture. Whatever it might be, guys love to feel like they’re needed. He’ll get to spend time with you, and you’ll be done with whatever errand you need in no time. That’s a win-win situation!

     15. What happened in your last relationship?

This is where things get personal. Get to know him and how he dealt with his previous relationship. Maybe it’ll give you an idea of where things are headed. If he asks, share your previous relationships with him, too. It’s only fair.

     16. What’s your favorite book?

This is a great way to flirt for avid readers. He’ll get to show off what books he likes and recommend his favorites to you. The best part is that you’ll be able to do the same. Talking about books will increase your common interests, which will help develop your relationship.

     17. What would you do if we were stuck alone on an island for three days?

This question is great to keep the conversation going. Before you know it, you’ll be talking for hours. You can machinate ways to survive on an island together. Who knows what interesting ideas you both will come up with? *wink*

     18. What type of boyfriend are you?

Probing questions like this one are a fantastic way to see how your relationship will develop. He’ll picture his life with you. It’ll be absolutely nice to imagine how this guy will treat you in the future.

     19. How would you describe me?

Does he find you interesting, cheeky, or geeky? He’ll be listing all the things he likes about you, and that’s always fun to hear. In a way, he’ll see those qualities for himself and realize what a great person you are.

     20. Are you seeing anyone?

If you’re not sure if he’s fair game, find out right away! Take the lead and let him know you’re interested. If he isn’t available, move on. There’s plenty of fish in the sea and no time to waste!

Let Him Know How You Feel

How do you pick the right flirty questions to ask a guy? Whatever you end up asking him, make sure you actively listen to what he has to say. Keep in mind some guys don’t talk as much as girls. Most of the time, it’s because they don’t have a chance to. Girls always end up dominating the conversation. Don’t make that mistake!

Once you have a great guy in front of you, reel him in, and show him you’re intrigued by him with these flirty questions. The conversation will flow more naturally the more you get to know one another. Good luck!


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