20 Flirty Questions to Ask a Guy


Interested in a guy? Dating someone and wanting to keep the fire burning? Want to ask him flirty questions to make him blush? Want to flirt with him subtly or very evidently?

Throwing away the conventional ways of letting the man initiate here are some questions that are going to let you take the lead. 

Here are some cheesy and flirty questions you can ask your crush or your man. 


Flirting is always considered one of the best ways to get closer to a person or to get a better view of their perspective about you. You might need to save some of these questions for the future! 

(I shall be your wingman and cheer you on!) 

If you’re interested in Him-

It’s always adorable and fuzzy when you like someone a lot but don’t know how to take it forward. That’s when subtly flirting comes in handy. 


Here’s a video from the popular YouTube channel Psych2go that may help you understand their answers to the questions. They talk extensively about how to identify and deal with psychological and emotional topics. 

further are more questions that might help you flirt with your crush as well as find out more about them!

  • What else do you do apart from being this charming? (Cheesy lines always make people giggle and blush) 
  • What is that one thing that you absolutely love about me? (Trick question. Pay attention to the answer. And work on it.) 
  • I was just thinking about you, do you want to hang out this weekend? (He’ll know that you think about him. *wink wink*)
  • Am I the only person who has seen this adorable side of yours? (If he tries to behave the same way often. You know it’s working.)
  • Have you ever woken up suddenly and felt that you’re in love? Or is it just me?  (Billy Ocean definitely deserves appreciation for this thought) 
  • You have such an amazing personality, how are you not dating anyone yet? (Another trick question. You’ll know if he’s interested in anyone or is dating anyone) 
  • How do you like ending a date? Or do I have to wait to find out? (If he doesn’t ask you on a date after this. You should probably just ask him out. I don’t think he’s picking up on your hints:\) 


  • What’s your ideal date night? Or should we go ahead with my planner?  (I mean it’s a good plan either way.) 
  • What is your love language? Do you like gifts? Or words of affirmation?  (Save this question for later!!) 
  • What song would you dedicate exclusively to me? (If it’s anything from Westlife to John Legend. Good going.)

If You’re Dating Him-dating-him

Dating someone and stopped flirting? Do you want to initiate it by asking flirty questions and making him blush? Here are some cheesy questions to ask your man. 

  •  What outfit suits me the best? Which is your favorite? (Be attentive towards the answer, and show up in his favorite outfit on the next date) 
  •  Did you always like me or was it something that developed over time? (Love at first sight or second?) 
  • What sounds like more fun to you, a picnic in a park or dinner at a romantic restaurant? (Plan a date accordingly!) 
  • Did you have a type? Or was I just enough? (I mean, you’ll know if he always had his eyes on you *wink*) 
  •  Apart from dating me, what are the other things on your bucket list? (Finding out about him to do list always helps with surprises)
  • What is your dream destination to travel to? Or does a countryside home with a farm excite you just as much? (You’ll know what your future with him will look like.)


  • What are you most passionate about? Are you particularly inclined towards advancing in a hobby or a passion? (you’ll have a clue about his future plans) 
  •  Did you know you made me a better person? And I like improving every day. 
  • You were in my dreams last night. Wanna hear? (tell the truth or make up a sweet lie. It’s in your hands )
  • Want to make a beautiful memory together? 

What to do if none of these questions really work? 

If none of these questions really give you the answer you’re looking for or do not give him the hints, or at least, he, very evidently cannot see the hints and pick on them, what to do? 

  • Communicate it directly- Sometimes, when sweet talks don’t work, you’ll have to take the direct approach. Ask him directly, talk to him about the lack of intimacy between the two of you, and how it gets really concerning.


  • Work towards establishing a stronger connection- You’ll have to take things in your hands and try to meet up with him physically and spend a day together doing things you both like. Always remember, there’s nothing better than a day spent well over a thousand text messages.  


  • He probably does not find any sense in the flirty way of conversation- So some people don’t really find any sense in talking to each other in a very flirtatious manner, hence they refrain from responding. NOT your fault, but that’s just how they are, so either you talk it out, or… give up.
  • He’s probably not used to it- Well, not all guys are well-versed with the coded language of communication. So there’s a good chance he has no clue what it is about. So you need to evidently show him or talk to him when you’re trying to say something.


  • How do I start the conversation? 

Greet. Talk about his day, talk about what he did, ask him if he missed you. And take it forward from there.

  • He doesn’t really respond to those messages and is rather quiet about it. 

He’s probably shy or isn’t used to talking in a certain way (or doesn’t really appreciate it.) Either way give it some time or just talk to him about his reaction. 

  • How do I make him flirt back? 

Well, make it a routine. Set a conversation style and make it a routine sooner or later he’ll start talking in the same manner. 

  • I don’t want to be evidently flirting with him but I want to subtly show my feelings. What should I do? 

(Act cute and shy) or rather pretend like you don’t know you’re flirting but use all the lines you can possibly think of. 

It is going to be a long process to work things out and figure out each other’s language of love, so have the patience it takes and give the effort it deserves and hopefully, things turn out for the best! And if it doesn’t, don’t lose your heart.