40 Questions to Ask Your Crush to Subtly Flirt With Them

By on December 30, 2016






We all know that the hardest thing about having a huge crush on someone is waiting to find out if they are crushing on you just as hard in return. It may be different if both parties are out and open about how they feel towards each other, but if you’re not quite sure that your attraction is required by your crush then you might want to play it safe. Playing it safe just means not being totally obvious about your feelings for your crush. In other words: Tread lightly, friend. Don’t come on too strong. You’re probably thinking, “Well, how can I flirt with someone without it being obvious I’m doing so?” Relax. There’s tons of ways to get that message to them in subtle advances. Primarily you will want to exhibit the appearance of being extremely intrigued by your crush. You will also want to take the time to get to know them on a more personal level. By asking the following questions, you will prove to whomever you’ve got that crush on that you like them- Without actually giving anything away! These questions will help you to further build a strong connection without smothering them in a heavily flirtatious atmosphere. Being too flirty can often times scare people away! Flirting doesn’t have to be hard or obvious, so we made it easy and subtle with the following 40 questions to ask your crush to subtly flirt with them:

How do you like to relax after a long day at work/school?

Getting to know someone starts off by getting to know what they like to do in their spare time.

 Do you like to go dancing? Would you want to go dancing with me sometime?

If a person didn’t have interest in you, would they ask you to go dancing? Possibly,  but highly unlikely. Dancing is a personal thing people do together. You have to be pretty close to them if you invite them to go dancing with you.

What’s the craziest thing you’ve ever done for someone while you were dating them?

Get personal and deep with this question! Asking about previous relationships is definitely a subtle hint you’re interested in them romantically.

What is something someone does that makes you feel nervous?

Find out which way to not act around them by asking them what makes them feel uneasy. They’ll surely appreciate your efforts to find out.

If we could get on a plane to anywhere right now, where would you like to go? Why?

What’s more spontaneous and slightly romantic than that? Yet it comes off as a simple question. Isn’t that perfect?

Can you describe what love means to you?

Prying about their definition of love means you care about their definition of it. Only crushes do that kind of stuff!

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What makes you feel comfortable around someone?

Just like asking them what makes them uneasy, asking them what makes them at ease is also important when building a flirt factor.

Do you prefer to talk over text or do you prefer to talk in person?

Why would you care about their preference if you weren’t interested in talking with them more often? Letting them know you’d like to talk more often is definitely a subtle way to flirt.

Do you believe in monogamy or open relationships?

This isn’t just a question you’d ask anyone. It doesn’t come off as you’re too into knowing, only makes it seem like you are just simply wondering. It’s a question that reveals the right amount of interest from you.

What are your ultimate goals in life?

Nothing says you care than finding out what their life means to them and what they want to do with.

What was it like the first time you fell in love?

Again, prying about relationships is the ultimate flirty way to show you’re interested.  

How are you still single?

This one is just cute and a form of flattery. Give it a shot!

How did you get to be so good at (insert activity here)?

Flattery, flattery, flattery! What more can we say?

What famous person do you find yourself crushing on the most?

By asking this you’re making it only slightly apparent that you want to find out what type of guy/girl they are into.

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Are you interested in dating someone at the moment?

This one is bordering on the lines of subtle and obvious. But it’s definitely a great way for them to feel you slightly flirting with them.

What makes you truly happy?

A great question to ask when if you’re crushing on someone.

What do you prefer to sleep in… If anything at all?

This question is a little racy and definitely heats up the flirt factor, but  almost in an unnoticeable way.

What’s the best gift you have ever gotten from someone you dated?

Doesn’t hurt to get some ideas for the future if things work out, does it?

How would you describe yourself in one paragraph?

Showing you’re interested in actually getting to know how they see themselves is important when building a stronger relationship with your crush.

What’s your favorite feature on the opposite sex?

Then you can tell him yours… Maybe like their gorgeous eyes?

What do you think defines the line between dating and close friendship?

That way you can find out how close you are to being more than just friends, if at all. Asking this question to subtly flirt with your crush is a great idea because it shows you’ve peeked interest in the subject. Hopefully they’ll start to get the hint!

What’s your favorite setting to get close to someone in? (I.e: a party, outside or at home.)

A sly way of letting them know you’ve been thinking about it and now you’d like to know.

What are your biggest turn ons?

No better way to flirt than to ask them what makes them tick in the romance department!

What’s the first thing you notice about someone when you meet them?

Figuring out how they think is vital in seeing if you two are compatible with each other.

What’s the dirtiest thing you’ve ever said you someone? What’s the dirtiest thing someone has ever said to you?

A fairly personal question to get your crush’s mind on the right path!

What would you sacrifice for love?

A deeper question you can ask your crush. It’s about love and talking about love falls perfectly in the flirt category.

Do you like to go hot-tubbing? Want to go with me sometime?

An invite to do something where you both are half-naked is always a perfect way to show slight affection for your crush.

What’s a perfect date look like to you?

Nothing says, “Hey I’m kind of digging you” like talking about romantic dates with your crush.

Why are you so hilarious?

Boosting your crushes confidence lets them know you care about their self esteem.

What was your first impression of me?

Getting to know how their brain works is crucial when it comes to flirting in a subtle manner.

Who should make the first move, a guy or a girl?

If they don’t know you like them by now, they might just be oblivious. However, to keep it simple you can play it off as something you’ve always just wondered and want to hear other people’s opinions on.

What do you like more in a partner, intelligence or looks?

A fun question to ask. Hopefully they answer right!

Do you like pet names? If so, what’s your favorite pet name to call someone?

Pet names aren’t something you usually discuss with your friends. Asking something like this might even be an invasive question for some. It’s a great way to flirt, maybe you’ll both start using these pet names in the future. Wink wink.

What are three things that you like about me?

Enough about your crush! Talk about yourself a little to keep things interesting. See if they respond to this the same way you’ve been responding to information about them. If they’re really listening, there is a good chance they like you back!

Do you think tattoos and piercing are considered sexy?

Finding out someone’s preference shows them you are genuinely interested in what they like and don’t like.

Are you into snuggling?

The answer better be yes. Snuggling is the best, don’t you think? Maybe it’ll inspire your crush to take action…

What’s your favorite way to kiss someone?

They may think you’re just curious, but with this type of question they may start to get the idea that you’re flirting.

Would you ever go skinny dipping? If not, do you want to try it sometime… with me?

Forget asking someone on a half-naked date. An invite to get fully naked is an even better way to show your crush that you’re digging them. But by doing it in a fun way, like skinny dipping, you’re not being super obvious.

Is everyone in your family as attractive as you?

Wowza. They’ll probably be blushing after this one.

What would you do if I kissed you right this second?

Hypothetically…. Or not hypothetically. That’s up to you to decide! However, if you ask this question, you might give away that you like them. But, who cares! Take a chance. Go for it and if they don’t like you back then it’s their loss, because you are a star and you deserve the perfect companion!

After mulling through these questions, your crush should have the right idea on how you feel about them! These are great conversation starters to get the two of you chatting away, all while flirting so low-key they won’t even know you’re purposely trying to flirt with them.





2 Comments

  1. his mate

    January 13, 2017 at 4:07 pm

    my crush and I got on so well that he met up with me every day for three days as mates, I was blow away via our connection that I said he was my soul mate in a previous life. We ended up getting drunk together and he dropped me off home although declined my offer to come in for a night cap. we continued to meet up as mates and i could not wait to see him again. Everyone knew i had a crush on him, but all i got was a kiss on the forehead and a ache to see him again.

    • web admin

      web admin

      January 14, 2017 at 11:24 am

      It is clear that the two of you are interested in each other. Try to spend additional time with him in the future. He may not believe that he should try to spend the night with you if you two have been drinking. Invite him over some day when the two of you are closer and no alcohol is involved. Speak directly and honestly with him about your thoughts and feelings at that time. Best of luck!

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