20 Flirty Questions To Ask A Guy You Like

By on September 20, 2013

Flirting can sometimes become an awkward thing to do if you don’t have very many good, flirtatious questions to ask. When it comes to talking to a guy you’re into you want to make sure that you are asking all the right questions and letting them know that you are into them, in a subtle way. So, how do you let your crush know you like them without telling them that you like them? Here are 20 flirty questions that you can ask a guy you like:


Question #1.) Have you been working out?


Why It’s Flirtatious: You’re complementing him! That’s Grade A flirting! Especially, since you are complementing him on not just one specific feature, but his whole body.


Question #2.) Are you single?


Why It’s Flirtatious: A guy will automatically assume that you are asking this question for a reason. Girls don’t ask this to guys they aren’t interested in. When you ask a guy if he is single, you are totally flirting.


Question #3.) What do you like to do better: Cuddle or Makeout?



Why It’s Flirtatious: Asking this lets the guy you like know that you are curious because you are interested in what one he likes better so that you can get down to it!


Question #4.) What are you looking for in a girl?


Why It’s Flirtatious: His first though is going to be, “Why do you want to know?” And he is going to think that you are digging around to figure out if you fit his ideal description. Flirt, flirt, flirt!


Question #5.) How can someone like you be single?


Why It’s Flirtatious: Unlike the plain ‘are you single?’ question, this one gives off way more of a playful flirt. You are complementing and asking a question. By asking how someone like him doesn’t have a girlfriend, you’re implying that it is unbelievable girls don’t try to date him every second because he’s hot or smart or funny!


Question #6.) What’s your favorite kiss?


Why It’s Flirtatious: You are digging to know what he likes best and could even be you slyly saying it’s time for your first kiss.

Question #7.) What’s your biggest turn on?


Why It’s Flirtatious: Only if you are truly into this guy, will you ask this question. And he knows that. You wouldn’t be asking if you didn’t plan on using that knowledge someday!


Question #8.) How did you get to be so hot/cute/adorable.


Why It’s Flirtatious: Again just one of those super flirtatious complements that will make him smile.

Question #9.) Do you think about me a lot?


Why It’s Flirtatious: You wanting to know if you’re on his mind a lot is telling him that you actually care and that you are thinking about him a lot, too.


Question #10.) Do you like romantic movies?


Why It’s Flirtatious: Asking this kind of lets him know that you are thinking of him as a person to watch romantic movies with… and the people you want to watch these movies with are usually someone you like.


Question #11.) What is your perfect idea of a date?


Why It’s Flirtatious: You want to know how he would spend a date and that let’s him know you are thinking of going on a date with him, but you want to make it perfect for him.


Question #12.) Do you have a date to the prom/dance/homecoming/event of any sort?


Why It’s Flirtatious: Why? Do you want to be that date? Obviously, you might if you are asking! FLIRTATIOUS 101. Maybe he’ll even ask you out!


Question #13.) How do you feel about the girl making the first move?


Why It’s Flirtatious: If he hasn’t made a move on you by now and you ask this question, it should give him the idea that you are thinking about taking that first step.


Question #14.) What are your turn offs?


Why It’s Flirtatious: Asking a boy to tell you his turn-offs implies that you will try to avoid that list of things in the future. Duh!


Question #15.) Where do you like to be kissed?


Why It’s Flirtatious: You may just get an eye-brow raise outta this one! This is flirting at its finest. You are letting him know that you are thinking about kissing him … and kissing him where he wants!


Question #16.) Do you think I’m sexy?


Why It’s Flirtatious: You wouldn’t be asking if his opinion didn’t matter.


Question #17.) Do you sleep naked?


Why It’s Flirtatious: Asking a guy you like this question let’s him know you are curious because you may want to know the answer for future reference if you sleep over. Or, maybe because you like to think of him indecent.


Question #18.) Would you be interested in going out sometime?


Why It’s Flirtatious: You have finally broken the ice and started talking about actually going out and doing something. You are letting your crush know you are ready to go out with him.


Question #19.) Did you know that you make me smile?


Why It’s Flirtatious: Taking him off guard and asking him something almost rhetorical will let him know that he does make you smile and that you love it.


Question #20.) Will you go out with me?


Why It’s Flirtatious: This one is more than just flirting. You are taking the initiative to see if all that flirting did its magic and hopefully, he’ll say yes!


  1. Cori-Uhh

    October 16, 2015 at 3:25 am

    So, I’m a freshman and I like this guy who’s a freshman. He’s really nice and he’s and engineering strand student at my high school. That’s how we met. I’m really outgoing and at first I just started talking to him because I thought it would be a good opportunity to make a new friend. For the first few weeks we just talked every once in a while saying random things here and there. But as homecoming approached I started to think about potential dates. So, I started talking to him more often. This was almost three weeks ago. After about a week I nonchalantly gave him my number. He didn’t text me. After fall break had passed without any word, I decided to let it go. By then, I really liked him. But when we got back and I had stop talking to him he greeted me excitedly. Saying hey talking to me in the halls. Lately, him approaching me. We talk everyday about pretty much anything. But he never did text me. Do you think he forgot? He’s not very outgoing like me and I know he doesn’t use social media or anything. Maybe he just prefers talking in person?

    • web admin

      October 16, 2015 at 7:29 pm

      He might just prefer talking in person–there is also always a chance that he just does not have a cell phone, so he cannot text you. The fact that he is excited to talk to you and talks to you all of the time (despite being so shy), makes it sound like he could have a crush on you. I would not say what his feelings are for certain quite yet, but it certainly seems possible. Stay friends with him, flirt with him a bit and see where things go. Good luck!

  2. Chichi

    September 7, 2015 at 6:07 am

    So, my friend has a crush on me , and he’s going on a date with one of my best friends. I honestly don’t know what to do… To try and explain how much he likes me, he kissed me! Three times. I don’t know what to do

    • web admin

      September 7, 2015 at 9:50 pm

      Do you like him as well? If he is currently going on dates with your best friend, then he is off limits for you at the moment (sorry!). It seems like he is very confused about his feelings though. Either he likes both of you, or he had a terrible idea to date her to make you jealous–obviously not a good plan. What exactly do you want to do? Do you like him? Does your best friend like him as well? Does he know how you feel? It seems weird that he would kiss you three times and date her–he’d have to know that you are interested and like him, and dating your best friend afterwards seems like a major misstep.

    • nugget

      November 5, 2015 at 2:10 am

      well…you have 2 options. You could ask him if he likes you or your friend, or you could tell your friend and see if he comes clean, if he doesnt then he isnt worth it, for you or your friend

      • web admin

        November 5, 2015 at 5:21 pm

        That sounds like good advice. Thanks for commenting, Nugget!

  3. Grace

    August 27, 2015 at 8:51 pm

    Me and. My family went to Naples to see my dads friend and I met this boy that I really liked!! He’s 15 and I’m only 13 he lives near me but I don’t know if he likes me and I don’t know what to say he might not even want to date a 13 year old we stopped talking as much and I’m rlly sad about it advice ?

    • web admin

      August 28, 2015 at 8:04 pm

      For the moment, your best course of action is to keep talking to him. As you get to know him better, you will be able to see if he is interested. We have an article on Her Interest that shows the signs that a crush likes you–check it out and see if he does any of the signs. In the meantime, talk to him as often as you can, flirt a bit and get to know him better. The age difference is not necessarily a factor; it just depends on how much it matters to him. Plus, getting to know him better will give him a chance to fall for you and develop the a crush on you in return. Good luck, Grace!

  4. Katie hensley

    July 25, 2015 at 5:11 pm

    Hey so I have this guy and we met through my best friend and he’s really great. I am starting to develop a crush on him and he wanted asked me to hang with him last night so I did and I feel like he likes me but I don’t know. When he texts me he always puts smiley faces and he never wants me to go. Help please?

    • web admin

      July 27, 2015 at 8:21 pm

      It sounds like he could be interested. Often, the best relationships are based on friendships. If you guys were to date, it would probably go really well. From the sound of your message, it seems like he is interested in you. Do you like him as well? Are you going to wait for him to make a move or are you going to make a move instead?

  5. alexia

    July 23, 2015 at 4:27 am

    Ok.I am in love with my best friend but everything is well cause he likes me too but he has a girlfriend and we r not even living near each other.He’s just here with me on his vacation. I need some advice plxlz

    • web admin

      July 24, 2015 at 4:00 am

      That is an extremely difficult situation to be with. Does he want to break up with her? Even if he did end things with her, you would still have to deal with the fact that you guys are far away from each other. Would either of you ever be moving? Personally, I would stay in the relationship (as long as you are okay with the ethical aspect of it) until you no longer want to just have a fling. After that point, you will need to have a serious talk with him about what you want. If he is unwilling to break up with her ever and neither of you is willing to move, then you will probably have to move on. For the relationship to ultimately work out in a few years, one of you will have to move closer and he will have to break up with his girlfriend. Good luck, Alexia.

  6. Ortance

    April 23, 2015 at 5:37 am

    am this really help, but I have some questions… Lol. So what if the guy U like is ur best friend ?How could u make him understand that u want a relationship?.. plz help

    • web admin

      April 24, 2015 at 2:48 pm

      That is a very difficult situation to be in. You have several options. The first one is to start flirting with him and hanging out with him more often. After doing this for a few weeks, you can try to make a move on him when you are hanging out. Since you are friends, you could also try talking about how you feel. An off-hand “Why haven’t we ever dated?” when he does something cute or makes you laugh could help to bring up the conversation more naturally.

      You should be careful, though, before you proceed. Once you have expressed your interest, it will be hard for your relationship to go back to just being friends and he will see you differently. Even if he feels the same, there is always a chance that it will not work out and you will lose a friend. As long as you know the risks going into that situation, you should be fine.

  7. Kalynn Jennings-Thomas

    April 21, 2015 at 7:19 am

    Would he think im crazy if i put all these questions on him at once should i like ask certein questions at a certein or go in for it??? Thanks!!!

    • web admin

      April 21, 2015 at 9:20 pm

      If you were to ask all of these questions at the same time, it would probably be extremely strange to him. Rather than asking these at once, you should slip them into the conversation. Every day or two, add another one of these questions into a normal part of the conversation. By doing this, you will be able to find out more about him without freaking him out too much.

  8. jesh

    April 19, 2015 at 10:58 pm

    Yeah I was called a creepy stalker

    • web admin

      April 20, 2015 at 7:15 pm

      Awww, that’s no good! These questions only work if you use them in the right way. Otherwise, it could end up weirding your crush out. You definitely need to slip them smoothly into the conversation for it to be normal sounding.

  9. Brittney

    March 9, 2015 at 1:39 am

    What if he doesn’t feel the same way about u?? I’m just saying!!!

    • web admin

      April 14, 2015 at 1:09 am

      That is true, but not too big of an issue. If he does not feel the same way, you will be able to figure it out fairly soon from his responses. Excellent question, Brittney!

  10. STAR

    February 11, 2015 at 12:46 am

    What if him& me both lived in different cities in the same state, will it still work.

    • web admin

      April 14, 2015 at 1:10 am

      These questions should still work perfectly fine from different cities and states. Your relationship will take more work, but that will be doable as well.

  11. layla eubank

    January 30, 2015 at 4:51 am

    Helped so much!

    • web admin

      April 14, 2015 at 1:15 am

      I am glad to hear that this helped you. Thanks for the feedback, Layla!

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