102 Questions to ask your crush (from dating coach Dan de Ram)

You have a woman in mind, and you want to make a move.

Or maybe you guys have been dating for a while, and you want to get to know them even better.

Either way, these 102 questions will guide you on how to make your crush yours.

BONUS, you’ll get a few additional questions that will help you get her in your bed.

By the way, have you seen my free Transformation Kit?

You'll get my best stuff absolutely free: 12 Opening lines that actually work, my 5 best texting tips (including copy-paste lines for Tinder), and the Friendzone Houdini. Download the Transformation Kit here.

After reading this article, you’ll know what questions to ask your crush to show her your attractive and exciting side.

How to use these questions on your crush?

Better not via text

If you barely know her, better to use these questions in real life than over text. However, texting or messaging on Instagram or Facebook is a good way to ask her on a date.

Wondering how to do that? Check out this page:

>> Asking a Girl Out Over Text – 9 Ways She Can’t Reject (+ Examples)

So use these questions offline.

The best way to get to know her is on a date.

Is this going to be your first date, and you want to blow her mind? Check out my ideas:

>> Ultimate First Date Guide for Men (21 Tips That Work)

Now that you know how to use them, there are 102 questions to ask your crush.

Find what makes her get out of bed in the morning

Asking what she’s studying or where she works is overrated.

This is something you ask at a networking event, not on a date.

Of course, finding out what she does for a living isn’t a bad thing to ask.

It’s something that, on average, occupies 40 hours of her week!

But how do you keep these questions fun?

Through talking about her internal drives.

In other words, the reason she gets up in the morning

Maybe it’s money, fame, or to lower the ecological footprint of the Netherlands so she can save the homes of polar bears.

Not only is this way more fun for her to talk about, but it also gives you a better understanding of who she is and if she’s your type!

Furthermore, these questions create a deeper connection, beginning a beautiful relationship or an adventurous night under the sheets.

How does talking about her internal drive lead to sex?


Talking about her goals and everything she wants to accomplish makes her super excited. And ready for an adventure 😉

Anyway, here they are!

  • What does your ideal day look like? (If she finds it difficult to answer, ask for three or five activities that complete her day)
  • From all the things you’ve done in the past year, what are you most proud of?
  • What do you prefer, a well-paying job but no spare time, or a low-salary job but you get to do whatever you want in the afternoon?
  • What do only a few people know about you that you wish to share with the whole world?
  • Do you want kids? (Don’t ask this on the first date but during a light conversation at a party or so)
  • What gives you satisfaction in your work?
  • What is your ultimate career goal? (If she doesn’t give you a concrete plan, then a career isn’t that important to her. In that case, you can use the next question)
  • What is the most important thing about your job? (Keep digging for answers by asking if she maybe changes lives, like in healthcare. Or if the money she makes is used for exciting trips. Or so she can keep updating her Hello Kitty collection because that’s what makes her happy for some reason)
  • If a doctor gives you one year to live, would you change anything about your life?
  • What is your most outstanding sports achievement? (Don’t ask if she works out. Everyone has a sports accomplishment, even if it was just winning a hotdog eating contest)
  • What is a bad habit you just can’t seem to break?
  • Who is your idol based on their accomplishments?
  • Name an item from your bucket list. What’s something you’ve always wanted to do?
  • What subject was the worst for you in high school? (Bridges to stories of skipping school and not following the rules mischief)
  • Would you ever jump out of an airplane? With a parachute. (If she says no, you can tease her a little)
  • What was the best day you’ve had in the past year?
  • What does our YouTube browser history look like?
  • What book left the biggest impression on you last year?
  • Who would you be happy to take care of? (Taking care of someone can feel wholesome)
  • Would you describe yourself as an introvert or extrovert?
  • What type of people do you have the best time with? And why?
  • If you could go back in time but not change anything and nothing could harm you, what year would you travel to?
  • What should I know about you that I would never think to ask?
  • If you could live anywhere, where would you live?
  • What makes a man attractive to you? (Primarily ask for the inner characteristic she likes)

She’ll probably name a few characteristics and qualities that you can further develop. You can read how to do that here:

>> 10 Proven Ways to Become More Attractive

Make her feel at ease with the following questions

Don’t ever forget this:

If she doesn’t trust you, she’ll never get into bed with you.

Shocking, isn’t it?

However, guys often forget.

Don’t launch question after question at her like a canon.

That way, the date will feel more like an interview, and she won’t get the chance to get to know you better.

That’s why you should answer the following questions yourself when you ask them.

She’ll feel more at ease and trust you with a better idea of who you are. In any case, she’ll probably answer these questions herself as well after you’ve answered them.

Here are the questions:

  • How is your relationship with your family?
  • Who do you have the strongest bond with within your household? Mom, dad, sister, brother?
  • Do you have pets, or have you had them? What did you like about them?
  • Who are your closest friends? What are they like?
  • Who took care of you when you last felt under the weather?
  • If you had to move to a deserted island, who would you take with you?
  • Who is your go-to person when you need support? (Don’t ask this question out of the blue. Tell her a story about yourself in which you looked for support from friends and loved ones when you went through a rough period. Or wait for the right moment)
  • Where do you feel most comfortable?
  • When you’re wandering around in nature, do you prefer the beach or the forest? (Most people feel calm in nature)
  • What music best relaxes you?
  • What’s your favorite comfort food?
  • What movie touched you the most?
  • If we watch a movie together, what genre would you prefer, comedy or horror? (Many women like to watch a scary movie with their boyfriends, as it enhances their feelings of being protected)
  • When did you feel the safest you’ve ever felt in your life?
  • What was the most unique, cozy, cuddly New Year’s Eve you’ve ever had?
  • Easter or Christmas? (Brings up memories of the holidays)
  • Who’s your favorite family member outside of your household? (Uncle, niece, third cousin)
  • Do you play an instrument? (This calms most people down)
  • In what city do you feel most at ease?
  • With what group of people do you feel at home?
  • What is your favorite dance? (Most dances get people feeling most at ease)
  • Who makes you laugh the most?
  • Who’s the last person you made laugh?
  • What is the most generous thing you have ever done?
  • When was the last time you received a helping hand when you didn’t expect it?

>> 145+ Must Have Date Questions to Vibe Deep into the Night

Questions to ask your crush to keep the conversation going


You won’t get anywhere if she falls asleep from boredom.

You’re doing something wrong if she gets bored during your conversation.

For that reason, you shouldn’t be too serious.

In the end, it’s less about the facts and more about the chill vibes.

You should throw in a joke here and there. If you need some inspiration, check out this article with jokes for you to steal…

No time for jokes? Then take a step back from the more profound questions and keep the conversation shallow.

Have you even been friendzoned?


Oh, then you’re not going to like this

(If you use this sentence, please do so with a playful stare and joking voice)

In any case, the following questions are here to keep her (and you) entertained.

Furthermore, they’re light-hearted and don’t take much energy to answer.

Even after seven beers and three shots of tequila, you should manage them.

  • Pizza or fries?
  • What cartoon character would you like to be for a day?
  • What influencer should be burned from YouTube, Instagram, and/or TikTok?
  • Would you prefer five tequila shots or three glasses of apple juice?
  • Do you ever do roleplay?
  • Your most incredible drug experience, go.
  • What’s the best song you’ve heard recently?
  • What was your best costume ever?
  • In what video game would you beat my ass?
  • Best movie of all time, in your opinion?
  • Do you see that cloud? Do you also think it looks like a duck?
  • Movies or series?
  • Being bright or beautiful, what would you choose if you had to?
  • Coriander, hell yes or hell no?
  • Do you prefer to read fiction or nonfiction books?
  • Who was your last celebrity crush?
  • Have you ever had a stand at a flea market?
  • Which fictional character is your idol?
  • Tell me something about your most annoying colleague.
  • How are your dance moves? (While asking this, pull her by the hand for a dance. 99% of women instantly get shy even if they are great dancers)
  • What would you do if you had an extra hour every day?
  • What’s the song that’s on repeat in your head right now?
  • What would you say if you could tell every man on earth something about women?
  • If I come by for dinner, what would you cook for me?

>> 7 Date-At-Home Idea Tips That Make All The Difference

Flirty questions that get her in the mood

Giggling and laughing is fun.

But it probably won’t get you under the sheets.

Might not even score you a kiss.

Nope. It leads to the friendzone.

That’s why flirty questions are a must.

BE AWARE Some of the following questions are sexual, which can work fantastically. However, sometimes your conversation isn’t there yet. In that case, change the subject.

Was that too much?

Yes, to be honest

Okay, no problem. Anyway, today I saw this hilarious thing (bla bla bla)

Pushback? Take a step back.

Do the jokes work well? Take it to another level.

And here they are, the questions.

  • What present would you give me for Valentines’ Day? (This question makes no sense, but it introduces romance into the conversation. Say it with a smile. Does she reply badly or unenthusiastically? Say Hah, relax. It’s just a joke. Anyway…)
  • When you get a tattoo of my name, will you place it on your arm or butt?
  • If we were married, would you cook for me every day?
  • You’re funny. Would you stay like that if we grew fat and old together?
  • What are the most romantic things you’ve ever heard?
  • What is the clumsiest date you’ve ever had?
  • Tell me your best kiss-gone-wrong story.
  • What romantic comedy has made you cry the most?
  • What’s the most romantic thing someone has ever done for you?
  • What is the most adventurous thing you’ve ever done for a man?
  • What man from Game of Thrones did you find most attractive? (It would surprise you how many women watch the series for that reason)
  • How would your boyfriend/date make you the happiest? With something exciting or something sweet?
  • What is the most exciting clothing item you own?
  • What is the weirdest place you’ve ever kissed?
  • Tell me your first love story.
  • Did you have a crush on someone as a kid?
  • What singer was your teenage crush?
  • Suppose you had to choose between loveless sex or sexless love. Which would you pick? (Paradoxical calls this question associations to love as to sex)
  • What was the best sexual experience you’ve ever had?
  • What’s something you still want to try out in the bedroom? (Be aware: these types of questions are best asked if you’ve already been together or if you both really feel that you can trust each other. Take a step back before it gets uncomfortable)
  • In your opinion, what is the most romantic language?
  • What song makes you feel warm?
  • What vacation destination do you still want to go to with your new lover?
  • Do you prefer to end a fantastic date with a kiss or sex?
  • Do you like gentle or rougher touching?
  • What is the weirdest place you’ve ever fallen in love with?
  • What physical characteristics do you find most attractive in men?
  • What was your most arousing experience ever? (You are asking for sexual tension here, not the deed itself. The answer might surprise you)

>> Sexual Attraction – 15 Things She Wants You to Know, But Will Never Tell You

Best questions to ask your crush

These were 102 questions that get your crush in love with you.

Even though these questions are rock solid, they might have the impact of a feather.


This is because questions are only as strong as the energy you put into them.

So, you have to say them playfully and confidently.

A great way to learn that is with my free Transformation Kit.

Get it below by clicking the big button and get all kinds of tips on how you could make your crush yours by tonight.

Good luck.

Your bro,
Dan de Ram.

Stop awkward conversations
and painful rejections

My free Transformation Kit will make you irresistible to women.

  • 12 Opening Lines that Actually Work
  • 5 Date Generating Texting Tips (Plus Copy-Paste Lines for Tinder)
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