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!

Question #21.) Would you consider yourself to be shy?


Why it’s Flirtatious: Asking this question may get a nice glow on your crush’s face as he blushes. If he is shy, it will be cute to watch him grasp for an answer and if he isn’t, then his confidence may just be worth seeing.

Question #22.) What are you favorite nicknames/pet-names?


Why it’s Flirtatious: This question establishes what names you two may favor in calling each other while flirting. Does he prefer babe or honey? You won’t know unless you dig deeper, girl!


Question #23.) Do you like dirty talk?


Why it’s Flirtatious: What could possibly be more flirty than you working on getting his mind in the right- or should I say wrong place? His answer will  give you the material you need to lead him into a very amusing conversation the both of you can indulge in.


Question #24.) How would you describe your ideal relationship?


Why it’s Flirtatious: All this talk of pet names and dirty talk may have things heated up, but opening up about what he would consider a perfect relationship might let your man know you truly mean business with him.


Question #25.)  Favorite place to make-out?


Why it’s Flirtatious: Are you both suddenly resisting the urge to lock lips with each other? Good, that is exactly why this question is so dang flirty. Maybe he will even want to show you where it is…


Question #26.) What did you first notice about me?


Why it’s Flirtatious: Was it your eyes? Your lips? Did he love the way you walk or talk? Shifting the focus of your conversations on yourself every once and awhile is a great flirt tactic. Get him thinking about what made him like you in the first place.


Question #27.) Do you have a secret fantasy and if so what is it?


Why it’s Flirtatious: Create a pathway for the both of you to chat about what really gets you going. Find out his deepest desires and what he likes, then see if he is interested in your secret fantasies. The answers to both are sure to bring your flirting levels to the absolute max.


Question #28.)  Do you like sexting?


Why it’s Flirtatious: Find out if you can continue to flirt even when you aren’t together! Asking these questions will get things riled up between you and the guy you are smitten with.


Question #29.) Do you think you could treat a girl right?


Why it’s Flirtatious: He may get almost offended with you for asking and hopefully respond with something like, “Well, duh, of course I would treat a girl perfect!” Watching a man get flustered over these type of questions is always cute, flirtatious fun!


Question #30.) How would you make me fall for you?

Why it’s Flirtatious: Listening to him list off all of the things he would do just to get you to fall for him is truly the sweetest thing you could be listening to. It is the perfect question when flirting with the guy you like. Who wouldn’t want to hear these sweet things?!


  1. sillow

    January 14, 2019 at 6:21 am

    I like this boy and he likes me but we found out I’m 8 months older than him .he insists just I just have to respect him not break up but I feel un confortable

    • web admin

      web admin

      January 14, 2019 at 6:56 pm

      His statement is unacceptable. You do not have to respect him, especially if he does not respect you. His age is meaningless. He should treat you with kindness and compassion. His behavior is unacceptable. Do not reach out to him in the future. Focus your emotional energy elsewhere. Determine what you want for your life without him. Have a great day, Sillow!

  2. madeline

    May 31, 2018 at 9:58 pm

    i have a question what if my boyfriend has a bestfriend that he wont let go and i dont trust her around him ?what do i do or any advice on how i should approach her or handle things?

    • web admin

      web admin

      June 2, 2018 at 3:12 pm

      Your partner and his best friend share history and likely an emotional connection. If the two of you find that your relationship has stress due to his friendship, then you will need to speak with him about your thoughts and feelings. They will also need to have a discussion as well. You will find benefit in being direct and honest with him. Give him an opportunity to share himself with you as well. Have a great day, Madeline!

  3. Carrie

    April 25, 2018 at 12:17 am

    I like my cousins friend and he looked intrested but he’s looks a bit afraid because of my cousin how should I approach?

    • web admin

      web admin

      April 25, 2018 at 8:48 pm

      It is likely that his apprehension to develop a relationship with you is due to your relation to his friend. Since you want to develop a relationship with him, you may find benefit in speaking with your cousin. Share your thoughts and feelings regarding this relationship. You may find that your cousin will approve of this relationship. Have a great day, Carrie!

  4. Alefiya

    March 9, 2018 at 12:19 pm

    What if the guy is interested but cannot except the feelings

    • web admin

      web admin

      March 9, 2018 at 9:55 pm

      This person may want to develop a relationship with you. It is possible that there is a reason why they are unable or unwilling to nourish a relationship with you at this time. Take this time to determine what you want for your future. Speak directly and honestly with him about your thoughts and feelings. Give him an opportunity to share himself with you as well. Have a great day, Alefiya!

  5. K_A

    March 8, 2018 at 10:00 am

    well i like this guy hes nice sweet and a bit of an asshole he knows i like him he said he would date me but at the time he said i was confused about my feeling and now im not but i dated his best-friend and his best-friend still likes me but im into this guy and i have no idea what to do

    • web admin

      web admin

      March 8, 2018 at 10:06 pm

      You have maintained a relationship with your crush’s friend. Your ex is still interested in developing a relationship with you. Your decision to nourish a relationship with your crush may harm his social relationships. Take this time to determine what you want for your future. Speak directly and honestly with him about your thoughts and feelings. Give him an opportunity to share himself with you as well. Have a great day, Ka!

  6. Cella

    December 29, 2017 at 4:27 pm

    What if he probably doesnt feel the same

    • web admin

      web admin

      December 30, 2017 at 6:49 pm

      Monitor his actions and words. If you believe that it is possible that he is interested in developing a relationship with you, then speak directly and honestly with him about your thoughts and feelings. Give him an opportunity to share himself with you as well. Have a great day, Cella!

  7. Zara

    November 4, 2017 at 4:37 pm

    I knew my crush 3 years ago then we stopped talking. About 2 years later I start talking again and he keeps sending me hearts and kisses and hug emojis. I got my friend to ask him out for me and he said maybe but in the end he said he liked me but didn’t really know me so no. he still sends me hearts and stuff. What should I do?

    • web admin

      web admin

      November 4, 2017 at 7:32 pm

      It is likely that he is interested in developing a relationship with you. It is clear that he still has a strong emotional connection with you. You do not need to speak with him through someone else. Speak directly and honestly with him about your thoughts and feelings. Give him an opportunity to share himself with you as well. Have a great day, Zara!

  8. anonymous K

    October 19, 2017 at 1:28 pm

    I’m in a relationship with this guy whom I love so much but he does claims that he loves but he doesn’t have my time. so I’m not sure whether he loves me or not. what must I do?

    • web admin

      web admin

      October 19, 2017 at 8:59 pm

      It is possible that he has strong feelings for you. He is always limited on time. If he is unable to show you his love, then perhaps his love for you is less important to him than the other things in his life. Allow him to fade from thoughts. New opportunities will become available at this time. Have a great day, Anon!

  9. S

    August 8, 2017 at 10:14 am

    I think I like this guy he is very kind, also funny. He is a year older then me. I just got dump by my boyfriend two months ago. I am not sure if I get into another relationship but I do like this guy. My friends said not to date him and then another said date him I just don’t know what to do please help.

    • web admin

      web admin

      August 8, 2017 at 7:10 pm

      Continue to spend time with this person. Take this time to determine what you want for your future. Decide if you are ready to develop a relationship with someone new. Speak directly and honestly with him about your thoughts and feelings. Give him an opportunity to share himself with you as well. Have a great day, S!

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