55 Questions to Ask Your Crush - Everything You Need!

55 Questions to Ask Your Crush – Everything You Need!

Knowing what to ask your crush to impress them and make them like you can be a nerve-wracking task. Don’t worry, that’s why I’ve compiled this list of the best questions to ask your crush (at all levels), whether you want to break the ice or take things to the next level.

My constant remedy to dealing with any kind of relationship (professional, personal, intimate, etc.) is to remember we’re all different and respond well to different topics… and therefore, will respond better to certain questions.

Hence why I came up with this list and categorized the questions into ones that will generally be OK to use in the beginning. And then I’ll give you racier questions for when you know him better.

In this article you will find (click ahead if you want to skip right to the questions):

Tips & Tricks

When in doubt, start small. Don’t just dive into questions you don’t feel comfortable asking right away. If you do not know him very well and aren’t sure about what to ask and whether he is interested in you, take it slow and let things build naturally.

Don’t try to force things if he’s not reciprocating the same level of interest.

Imagine how you would feel and have probably felt in the past if a guy came onto you in an extremely forward fashion, trying to pursue you without even knowing whether you’re interested. What does it feel like? Take this and apply it when and if you are in a situation where you don’t necessarily know how he feels.

Having a Crush is Fun

If you’ve got a crush, a relationship is definitely at play, or at least I’d assume the fantasy of one. You know him and see him, and admire him for what and maybe who he is. Sometimes I miss the feeling of having a crush and the excitement and energy you feel when just getting to know someone you are really interested in. So I’ll consider anyone reading this lucky. Having a crush is a fun exciting thing with a list of any possibilities.

You have a crush, but you might be wondering, “How would I get someone interested in me who has no idea how I feel without being awkward and embarrassing myself? How to I get the person I like to like me back? How would I get that “apple of my eye” to come to me when they want to talk, or even better, when they need to talk?!”

Determine What “Kind” of Crush You Have

In other words, are you a viewer of your crush from afar? Or is this a friend that you’re gaining feelings for?

The kind of questions I recommend asking are dependent on on your relationship to your crush. Certain questions are obviously OK for someone you know that would be inappropriate to ask someone you’re trying to get to know.

It might not seem super easy, but is a lot easier than you’d ever think.  Hopefully, I can give some insightful, yet subtle questions to pique his interest. And by subtle, I mean coming off as totally candid.

The reason I say “subtle” is because if you don’t know how he feels about you yet, it’s best to start small and build up from there.

You want to know he likes you as well before you take that next step. These questions can help you get a feel of his reciprocation, as well as spark some conversation to at least get to know each other better.

Take The Quiz: Does He Like You?

Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you…

So here are some simple subtle questions to move towards a closer connection!


Starter questions to ask your crush (Safer/Subtle):

  • Do you like animals?
  • Do you have a favorite pet?
  • Do you like your job?
  • Who is the best the musician in your mind?
  • If you could move anywhere, where would you go and why?
  • What would be your dream profession?
  • If you won the lottery what would you spend your winnings on?
  • If you could have any car what would it be?
  • If you could marry anyone right now who would it be?
  • What are you doing this weekend with your friends?
  • What’s your favorite thing to do after work?
  • Has anything happened that changed you?
  • Have you ever been into a cringey fad?
  • What do you hate the most right now?
  • What’s stressing you out right now?
  • How do you wind down?
  • Favorite hobbies?
  • Funniest thing you’ve seen/ done?
  • Craziest thing you’ve seen/done?
  • Biggest turn ons?
  • Biggest turn offs?
  • Most embarrassing moment of your life?
  • Crazy family members?
  • Favorite sport?
  • Do you play any instruments?
  • What’s your favorite subject?
  • Most trouble you got into as a kid?
  • Any obsessions? Gaming? Social media?
  • Have you ever just barely gotten away with something?
  • Do you have any special talents?
  • Were your parents strict growing up?
  • Have you ever had to prescribe to any insane policies for a job? School, etc.?
  • What’s the most trouble you’ve ever been in?
  • Where the most beautiful place you’ve been?
  • If you could live anywhere where would you move?
  • Have you ever related to any character in a film?
  • What are your top 5 movies?
  • Do you have any favorite shows?


Flirty, fun, and “racy” questions to ask your crush:

  • I like your outfit where did you get it?
  • Do you workout?
  • Are you taken?
  • How can someone like you stay remotely single?
  • Has anyone told you how handsome you are?
  • You know how good look right?
  • What would be your craziest date idea?
  • You mom and dad are good looking right?
  • Have you ever been caught in an “odd” situation?
  • What’s the most embarrassing thing that’s ever happened to you in front of a girl?
  • Who is the hottest celebrity?
  • Are you into boobs or butts?
  • What would you do to me if I said you could do anything?
  • How much would you have to get paid to streak around your block?
  • Are you a boxer or brief kinda guy?
  • Are you strong enough to pick me up?
  • Would you ever wear a speedo?

There you go! Now you have a list of the types of questions you can ask your crush. Whether you’re starting to get to know him or heading in a direction toward a deeper connection, one key takeaway is to always be present and listen to him.

Listening Is the Heart of Having a Connected Conversation

Part of listening means you are not stuck in your own thoughts wondering what he thinks of you or trying to impress. In fact, trying to impress will sabotage your interactions and make it impossible to truly listen.

Ironically, when you stop trying to impress and realize that the only thing that matters is being engaged in the present moment and seeing how you get along as people… you free yourself of the most sabotaging conversation killing energy.

Once you drop the mindset of trying to impress, what can you do to be fully present in a conversation with your crush?

Observation is Key

One rule to always keep in mind is to always have a good gauge of the “vibe” of the situation, unique personality as well as situational and environmental factors. In other words, take the context of the situation into consideration. If you’re in a club, you can act and speak differently than a church ceremony.

Consider Context

Have a good idea of how he’s feeling before you ask any questions, so you can ask the questions that work best at that time.

You can never know how someone’s feeling, or what happened to them that day or in the past. People can be all over the spectrum. Men (just like women) can be all smiles on payday, or sullen and depressed after losing a pet.

You never know- so please always listen to what you hear and feel. Listening is both crucial to what’s being said verbally, and also to nonverbal, visual cues. Listening requires your ears and eyes, especially while conversing.

Listening is about both hearing what he is saying and observing him and his body language, facial expressions, etc.

Nonverbal Cues Will Make All The Difference

Nonverbal cues can be the most important and are usually stating the true feeling of the person. A good example could be, “How was work today?” and with a sunken face he replies “Good,” in a monotone drone. His day wasn’t good, he hates it! In this example, you could gauge the situation and ask why he doesn’t like work etc.

Always try to understand the person you’re interested in objectively.

Guys can obviously be shy too, and sometimes coming on strong can be a deal breaker! Depending on the guy! So it is vital to listen to those verbal, and non verbal cues.

The main thing is to go with what feels right and comfortable for you. If you’re a charismatic, fun girl, be that! Ask the questions in which you see best fit your personality.

Think of it like this: When you’re asking questions that fit your personality, you’re playing to your own strengths.  And if you’re playing to your strengths, then all of your conversations will be within familiar territory for you, which means they will be smooth, effortless and comfortable for you. Your comfort is contagious – it will help put him at ease and help make him more comfortable to open up to you.

Relationships are beautiful things that supersede sex. Through relationships, we can understand all people. We learn to not only accept faults but love them. So I want success for everyone in their love life!!! Trust me!

And finally… have fun!!! If you come from a place of fun and happiness, you will bring this energy into your interactions with your crush. And when you come from a place of fun, he will want to spend time with you! Don’t put pressure on the situation. Simply let things happen naturally and enjoy it! Trust me, nothing is more attractive to a man than a happy woman.

Want more questions? Well, look no further…

Personal questions to ask a guy… these are amazing questions to really understand who he is.

Questions to ask a guy… if you’re ever lost or unsure about what to say, these questions will give you confidence.

Truth or dare questions… this can open up a whole new world of information you never knew about your crush. Embarrassment will be a reality.

Never have I ever questions… this “game” can actually be a ton of fun and works to break the ice!

Even more great questions to ask him:

225+ Amazing Questions to Ask a Guy: The Ultimate List

230 Questions to Get to Know Someone: Most Effective Questions to Ask

20 Questions to Ask a Guy You Like to Get Closer

Questions to Ask Your Crush

15 Questions You Are Too Afraid To Ask Your Crush

25 questions to ask your crush to see if you should be with them

Want to find out if he really likes you? Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you…

Take The Quiz: Does He Like You?

6 comments… add one
  • jessica February 21, 2018, 6:47 pm

    i love the flirty, fun questions! this will not only make me excited..i’m pretty sure he’d feel the same! lol!

  • eva February 20, 2018, 11:12 pm

    super like this list of questions! but of course you should really be careful to listen and understand what he’s trying to communicate. communication is always 2-way.

  • kaylee February 19, 2018, 12:23 pm

    love these ideas! :) i like this new guy at work and i’m hoping i could get to know him better.

  • Jess February 11, 2018, 10:05 am

    I love this list… I am going to save this on my phone and pull it up when I am around my crush so I have questions to ask him. Thanks!

  • raizza February 5, 2018, 11:40 pm

    it’s true, don’t ever force things. some men take time to really open up themselves to women.

  • samantha January 31, 2018, 10:14 pm

    Love the flirty flirty stuff!

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