21 Flirty and Deep Questions to Ask Your Crush

Updated on June 13, 2019
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Sam wishes you happiness forever in your relationship. And if you aren't in one yet, it will be OK! Everybody's been there.

Got a crush? This list of 21 questions to ask your crush is specifically tailored towards developing a relationship with that special person you've got butterflies for. With these questions, you’ll be able to find out their true feelings towards you and also clue them into how you feel about them. The best part is that these questions are designed to be casual and subtle, so even the shyest among us can ask without feeling like we’re trying too hard or are being too obvious.

1. What Do You Think About Before You Fall Asleep?

This is a great casual question that can also be intimate and deep. You’re not directly asking if they’re crushing on anyone, but the result will be similar—you’re giving your crush a chance to tell you if there’s a special someone who’s always on their mind. If they say they think about you, then they most definitely have feelings for you.

2. If I Called You Really Late at Night, Would You Answer?

If they say yes, then they clearly care about you. Of course, don’t take this as a sign that they have romantic feelings for you because friends would also pick up their phones late at night (you never know whether your friend is having an emergency).

3. What’s the Biggest Deal Breaker on a Date?

Avoid doing whatever they say. Or, if they say the biggest deal breaker is playing country music in the car or wearing too much makeup and those things are your jam, then you two are not compatible.

4. If You Could Dedicate a Song to Someone You Love, What Song Would It Be and Why?

Song lyrics can say so much about how someone feels deep down inside. Analyze the song they give you, and if the story or the message matches your situation with your crush, then you know for sure they’re trying to hint they like you too!

5. What’s the Perfect Way to Ask Someone Out?

If your crush gives you a generic answer, like “I would just ask her after school,” then he probably doesn’t have a crush at the moment and hasn’t put much thought into asking anyone out. However, if you crush gives a more considerate answer, then you can infer that he has thought about it recently and currently has someone on his mind he’s planning to ask out!

6. How Do You Know When You’ve Fallen for Someone?

You’re literally giving your crush a chance to tell you they like you with this question. If they’re ready to open up, they will hint at it or flat out tell you.

7. What’s the Most Important Thing in Your Life Right Now?

Asking what they find important in this moment is a great gateway to finding out what their short term plans are for their life. If they really like you, they might say, “Having a gf or bf.” Or they might say, building up the courage to do “things.” You can pry further to find out what that “thing” is.

8. Describe Your Ideal Type in 5 Words

See if you’re the one. If you are, your crush will describe you in 5 words. It also helps to note if they only describe superficial things, like physical appearances. If you really want to be with this person and not just hook up with them, then you will want to choose someone who can describe their ideal person using words like “intelligent,” “kind,” “has a sense of humor,” “cares about animals,” etc.

9. What Are Your Top 3 Things to Do on the Weekend?

This question lets you find out what they’re really like and what their true hobbies are. If your crush says “nothing” or “I just sleep and watch T.V.,” then they either aren’t interested in talking to you or they’re just not an interesting person.

10. If You Had All the Time and Money in the World, What Are 3 Things You Want to Do?

Again, asking something like this can paint a very clear picture of who this person truly is and what they care about most. It allows you to see whether you have compatible world views and personalities.

11. Do You Prefer Casual Dating or Long-Term Relationships?

A very important question to gauge whether you’re both on the same page. You could both like each other, but if one is about serious dating and the other is just looking for something casual, then the relationship will end up not working, and you’ll regret it.

12. Would You Rather Date Someone Smart or Hot?

Asking this let’s you figure out whether you’ll be compatible. If you are not superficial, then hearing them say they’d rather date someone hot is a big no-no. However, if you are all about sexual attraction, then you’ll get along swimmingly. This question also gives you a chance to probe further. You can get more details by asking follow-up questions like “Do you prefer a nice face or a nice body?”, “Do you like blondes or brunettes?”, etc.

13. What’s a Gift You’ve Always Dreamed of Receiving?

This is such a cute question because it can tell you so much about what your crush cherishes, and if you wanted to go all out and get them a gift, you’ll know exactly what to get them.

14. Have You Ever Experienced Unrequited Love?

This is a veiled question about whether they have or are currently feeling like their feelings aren’t being reciprocated. It opens the door to a possible confession about having feelings for you.

15. Do You Idealize Your Parent’s Relationship?

Whatever their answer is will tell you exactly what they envision for themselves in terms of dating, marriage, and their future life partner. If they say they don’t believe in marriage because of xyz, then you’ll know that they have possible commitment issues. If they acknowledge certain pitfalls in their parent’s marriage and say that they want to try avoiding it, then you’ll know that they are looking to create a good relationship and will work hard to maintain it.

16. If Someone You Liked Didn’t like You Back, What Would You Do?

This gives your crush the chance to prove how strong their feelings are when they have a crush. Are they the type to just move on to the next best thing or do they harbor feelings?

17. What Are You Most Scared to Do?

Someone’s particular vulnerability paints a crystal clear picture about the things they care about. Whatever they are scared of doing shows that they care a lot about that thing. For example, if they’re scared of not getting into the right college, they put a lot of care into their education and future. If they say they’re scared of ending up alone, then they are a true romantic who cares a lot about find true love.

18. What Do You Get Nervous About the Most?

They could say something like taking a test or meeting new people, but if they really like you, they might just say, “Asking you out.” OMG!

19. Would You Rather Find the Love of Your Life or Be a Millionaire?

Are they a romantic or superficial? The answer to this question will reveal everything.

20. What Are You Superstitious About?

Do they believe that things can happen outside of their control or are they a straightforward person who thinks everything happens for reason? More importantly, does what they believe in align with your beliefs?

21. What Is the Nicest Thing Someone Could Do for You?

If they say, “Listen to me and understand me,” then they’re a keeper. If they saying, “Buy me a car or a house,” then they don’t have much depth to them. You choose whether you want to spend time with them after that…


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    • profile image


      4 weeks ago

      Hey these questions helped!.

    • profile image


      2 months ago

      Omg! When we talk, it seems like he really cares about what im saying

    • profile image


      2 months ago

      Im not really that close with my crush how on earth will i start convo with him...it kills me

    • profile image

      Savage queen 

      3 months ago

      I tried this thankfully it worked

    • profile image


      4 months ago

      Wowwww this tots helped! He always stares into my eyes when he talks..... SO CUUUTE!

    • profile image


      5 months ago

      awesome quizes let me try them out

    • profile image


      5 months ago

      Legit questions

    • profile image


      5 months ago

      Oki doki

    • profile image


      6 months ago


    • profile image

      jus' me 

      6 months ago

      Some were great, and iv'e used them, but some i wud NEVR use..

    • profile image


      7 months ago

      Ur wrong.Guys just like cars.

    • profile image

      Some boy 

      7 months ago

      Legit the best questions to ask your crush. I’ve asked all these questions to my crush and she answered all of them in depth which was good because then it led to other conversations. Best question I reckon I asked was

      “What’s the nicest thing someone can do for you”?

      I got a little insight of expectations and what not.

    • profile image


      9 months ago

      These were good but some were a little bit to awkward

    • profile image


      10 months ago

      Nicole you should give them a sheet of paper and then ask these questions as a quiz then tell them to give you the paper.

    • profile image


      10 months ago

      I feel like maybe I should try this... I'm just not sure how I'm going to start a conversation off this way though, plus, he has his own friends and wouldn't make time for me asking somewhat awkward questions... I'm too awkward to pull off a deep convo, or even to get his attention in the first place.

    • profile image


      11 months ago

      I'm going to try a few of these....

      Don't want it to get Awkward!!!!!

    • profile image


      12 months ago


    • profile image


      13 months ago

      really nice will try....

    • profile image


      16 months ago

      This good

    • profile image


      18 months ago

      Ok this

    • profile image


      19 months ago

      nice thoughts


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