100 Questions To Ask Your Crush To Keep The Conversation Going

Funny questions to ask your crush

Are you running out of things to ask your crush? Don’t fret. We’ve got you. Yes, we know how excited you are that your crush finally replied to your DM and is eager to chat with you.

And we also know that you don’t ever want the conversation to end. If anything, you would want the conversations to spill out of the inbox into face-to-face convos.

But then there is the issue of knowing what to talk about. You may not be great at bringing up topics for discussion, and that is why we are here for you. In this article, we will supply you with a vast array of questions you can use to ensure those DMs from your crush keeps coming.

 

 

Funny Questions To Ask Your Crush

truth questions to ask your crush

Take a look at some funny questions to ask your crush

 

1.  What Is The Funniest Joke You’ve Ever Heard?

This should top the list of things to ask your crush to make them laugh. If they have a joke, they consider the funniest, retelling it will crack them up.

 

2.  What Is The Dumbest Pick-Up Line Someone Has Used On You?

This is another question that will bring smiles to your crush’s face, especially if they are beautiful and have many admirers.

 

3.  What Will You Do If You Can Change Your Gender For 30 Days?

Listening to your crush answer this question can be really fun. It will also give you insight into how your crush sees people of your Gender and, perhaps, how they see you.

 

4.  Most Embarrassing Moment In College?

Admittedly, embarrassing moments are not funny when they happen. But they are when you recount them later.

 

5.  What Is the Worst Prank You’ve Ever Fallen For?

Most people have been pranked at one time in their life, and the realization that you had been pranked is pricelessly funny.

 

6.  Who is Your Favorite Skit Maker/Comedian?

This question can lead to you playfully arguing, especially if your favorite comedian differs from theirs. It can also be an avenue for you both to bond if her favorite is yours.

 

7.  What Naughty Thing Would You Do If You Will Never Get Caught or Seen?

Asking them this question will reveal to you their guilty pleasures.

 

8.  What Is The Most Annoying Nickname You’ve Ever Had?

When you ask your crush this question, you are handing yourself a ticket to their memory lane.

 

Truth Questions To Ask Your Crush

Truth or dare is one of the things to ask your crush to keep the conversation going. But sometimes, you two can’t do dares because you might not be together physically. So, the best option is playing truth. So, here are some true questions to ask your crush in that regard.

 

1.  When Was The Last Time You Lied About Your Age?

It is common for people to lie about their age. For younger people, they increase their age to look mature, and for the elderly ones, they reduce their age to fit in.

 

2.  Which Parent Is Your Favorite?

Everyone has a favorite parent, even though they might not want to admit it.

 

3.  Which Celebrity Would You Like To See Naked?

Many people have celebrity fantasies; it wouldn’t hurt to know your crush.

 

4.  Will You Go Back If Your Ex Comes Calling?

Many people are looking for a chance to return to their former lover. This question will help you know if you stand a chance or not.

 

5.  Whose Call Can You Not Answer On Loudspeaker In Public?

We all have that one friend who doesn’t give a rat’s ass about what anyone thinks, the one that can put you in trouble by just opening their mouth.

 

6.  Last Time You Went Down?

You have to evaluate how close you have become with your crush and the boundaries of what you two discuss before you ask them this.

 

7.  What Would You Do If I Walked In On You Naked?

Like the question above, evaluate your closeness and boundary of discussion before asking this raunchy question.

 

8.  Have You Ever Lost A Fight?

This is another question that will take you down memory lane.

 

Questions To Ask Your Crush To See If They Like You

Here are some of the things to ask your crush to see if they like you:

 

1.  What Was Your First Impression About Me?

The goal is to know what they think about you. What better way to start than this?

 

2.  Is there anything You’d Like To Know About Me?

Asking this is an avenue for your crush to ask their question, too, in case you have been the one asking. If your crush is interested in you, there would be many things they’d want to know. If they are not interested in you, they might say no.

 

3.  If You Had The Means, Where Would You Like To Take Me?

The answer to this question shows how much they think about you. If someone has a place they want to take you to see, chances are that they have been thinking about it a lot; they have been thinking about you a lot.

 

4.  Do You Enjoy Spending Time With Me?

When you ask them this, you discover where you stand with them. They won’t think or say you are too much if they like you.

 

5.  What Is Your Favorite Picture Of Me?

So, you two met online, and you asked this. Should they produce a picture, that means they have been checking you out.

 

6.  Would You Be Mad If I Kiss You When We See?

This question will put them on the spot but will also show if they like you. If they do, they’ll say an outright yes or maybe blush. But if they ask you, “Why Would You Kiss Me?” that means they don’t like you that much.

 

7.  Would You Want To Visit Me?

Oh, if they like you, they’d definitely want to be around you.

 

Things To Ask Your Crush Over Text

Ask your crush these questions over text to keep the conversation interesting.

 

1.  What Is Your Best Way To Spend A Weekend?

If you ask your crush this, it gives you insight into some of their hobbies even without asking.

 

2.  What Is Your Favorite Movie?

This question can lead to you two talking about movies and giving each other hints about other great movies you have not seen.

 

3.  Which Social Media Platform Is Your Favorite?

Many people have different platforms that they prefer. If you and your crush met online, then there is a chance they have a favorite platform.

 

4.  E-books Or Hardcopy?

If your crush is bookish, this is one question you can ask them.

 

5.  Can You Tell Me The Things In Your Bucket list?

Knowing the things on their bucket list tells you the kind of person your crush is.

 

6.  Texting Or Phone Calls?

This question will tell you how to approach your crush. If they say they prefer calls, that means you have to switch to get their attention.

 

7.  What Is The Saddest Thing You’ve Heard This Week?

Life is a mix of the sad and the happy. This question will show if your crush is deep or superficial.

 

Cute Things To Ask Your Crush

1.  What Song Can You Sing From Start To Finish Without Mistakes?

This question will show if your crush is a music person and to what extent.

 

2.  Do You Think You Are Attractive?

The reply you’ll get from this question will show if your crush is proud, has a healthy self-image, or has low self-esteem.

 

3.  What Is The Sweetest Thing Someone Has Ever Told You?

This question gives you a chance to know what makes your crush tick.

 

4.  How Many Kids Do You Want To Have?

This is a cute question if you both are hoping for something long-term.

 

5.  What Was Your Favorite Cartoon?

This gives you an insight into how their childhood was.

 

6.  Do You Find Bearded People Hot?

You can sneak in this question if you are bearded and hoping to see what she thinks about your kind of people.

 

7.  Can You Send Me Your Goofiest Picture?

If they send this, then they actually like you.

 

8.  If You Won A Lottery Now, What Would You Do With The Money?

This gives you a chance to know how financially literate your crush is.

 

Interesting Things To Ask Your Crush

1.  Which Country Would You Rather Be Born Into?

If given a chance, most people would switch nationalities. Maybe your crush too. Remember to ask them why, as this would make the conversation more interesting.

 

2.  Do You Think We Share Any Similarities?

This is one question that could lead to your crush introspecting. If you like quality conversations, you should ask them this.

 

3.  What Is One Place You Would Love To Visit?

This will unearth your crush’s wanderlust.

 

4.  What Is One Thing Most People Don’t Know About You Easily?

Asking them this will cause them to unravel themselves to you, that is if they like you.

 

5.  Do You Like Planning Or Spontaneity?

This will give you a clue on how to relate with them. If they like planning, a surprise date may not really wow them as you would think.

 

6.  What Is One Thing You Spend Much Of Your Money On?

This question lets you know the indulgences your crush engages in.

 

7.  Are You A Superstitious Person?

You may need to have this detail to know exactly how to behave around them, what to take seriously and what to joke about.

 

8.  That Thing Do You Think Is Overrated?

This will make an interesting line of conversation no matter where the answer goes. If you agree with them, you two get something to bond over. Do you disagree? You two have more things to discuss, like why you think they are wrong.

 

Things To Ask Your Crush To Get To Know Her

Want to know things to ask your crush so she doesn’t get bored talking to you? Here are some of those questions to ask her:

 

1.  Do You Like Working Out?

You could ask her if you are big on health and exercise. Who knows? You can get a crush and a gym buddy all in one.

 

2.  Are You A Morning Or Night Person?

This will give you a clue about her habits.

 

3.  What Are Your Hobbies?

Asking her this will let you in on things she enjoys doing. You could see one or two that you also like doing from her answers.

 

4.  What Can You Do Perfectly Without Practice?

This question will let you know her superpower.

 

5.  What Name Would You Rather Bear?

When you ask her this, it tells you how satisfied she is with herself.

 

6.  Do You Have A Fondest Memory Of Your Dad?

This question will hit home if her dad is her favorite parent. It will also take you down her memory lane.

 

7.  What Are You Most Passionate About?

If you are a team living with a purpose, this is an excellent question to ask someone you have a spark for.

 

8.  What Do You Think People Like About You The Most?

If she answers this, cross-check if that tallies with what you like most about her. If they are the same, you can tell her. If it is different, you can tell her your opinion as well.

 

9.  Favorite Ice Cream Flavor?

This will come in handy if you intend to surprise her with ice cream and pies.

 

10.  In A Relationship?

You’ve got to ask her this early so you don’t go on a wild goose chase.

 

11.  What Is The Most Romantic Thing Someone Has Done For You?

You ask her this to get a clue about what she thinks romance is. You’ve got to speak her love language, you know.

 

Things To Ask Your Crush To Get To Know Him

1.  Do You Have A Girlfriend?

Knowing this early enough is better so you don’t water someone else’s vegetable.

 

2.  What Is The Silliest Thing You’ve Done For A Girl?

People do silly things when they are in love sometimes. So you can have a good laugh listening to your crush recall something he did.

 

3.  Would You Rather Your Girlfriend Be Attractive or Smart?

Most guys would say they want an intelligent girl till it comes to choosing between bright and pretty. So please sit back and watch him do the battle between choosing hot or clever.

 

4.  Ever Kissed At First Date?

Some guys can get down to it on the first date; some can’t. This question will show which side of the divide your crush belongs to.

 

5.  What Is Your Favorite Sports Team?

You may not be into sports, but there is a high chance your man would be. Most men are. Asking him this will make him realize that you are interested in knowing more about him.

 

6.  Still In Touch With Your Childhood Best friend?

This question shows how much he is invested in keeping old relationships.

 

7.  Do You Like Cooking?

Some guys still think cooking is a woman’s job. If you are a feminist, this might be a good question to ask.

 

8.  Who Was The Last Person You Broke Their Heart?

Asking him this would make him chuckle for sure. But, it will also tell you if you are a player.

 

9.  Do You Live Alone?

Oh, come on, you know why you should ask that, don’t you?

 

10.  Dream Job?

Most people don’t eventually end up doing what they want to do. Life seems to make us play different roles other than the ones we had auditioned for. This question might reveal those hidden dreams.

 

Deep Things To Ask Your Crush

things to ask your crush over text

Some people like deep conversations and may not want to dwell a lot on the superficials. You prefer thoughtful questions that can cause one to push the limits of your mind. If you are in this category, don’t worry. We’ve got you too. Here are a collection of deep questions to ask your crush:

 

1.  Do You Like Where You Are In Life Now?

This question will lead to serious introspection that could continue days after the question has been asked.

 

2.  What Would You Do Differently If You Could Go Back In Time?

Most of us grow and rue the chances we missed. This is an opportunity for you to see these missed opportunities from their point of view.

 

3.  Who Is Your Go-to When You Need Advice?

Mentors, families, and friends are there to guide us when we are confused. This is a chance for you to meet the authority figures in your crush’s life.

 

4.  What Scares You The Most?

Everyone has a fear that gnaws ever so silently. There are lots of what-ifs that could keep an adult awake. Asking this will introduce you to some of those fears.

 

5.  What Will You Do If Your Significant Other Cheats?

This will give you insight into how your crush takes cheating.

 

6.  Who Is The Most Important Person In Your Life Now?

This question is a necessary one to ask. It shows you where his heart is.

 

7.  Do You Think We Are Here For A Purpose?

Some people think there is a reason humans are here; some people think otherwise. This question will show which part of the divide your crush belongs to.

8.  Any Relationship Red Flag?

It is vital to note red flags for you and your crush. So that both of you would know when to break into a run should the other person start flying the red flag?

 

9.  Do You Believe In The Afterlife?

Some people believe it all ends here. Others believe there is another place beyond the grasp of mortals where we go when we die. You can explore this theme with your crush. It makes for an exciting conversation.

 

10.  Are You A Logical Or An Emotional Person?

This question is a must-ask so you know how to treat them. An emotional person may take things to heart easily. Therefore, it is always good to guard what you say around them.

 

Things To Ask Your Crush To Keep The Conversation Going

questions to ask your crush to see if they like you

Here are some other questions you can ask your crush to keep the conversation going.

 

1.  Do You Care What Others Think Of You?

Some people may care about what others think, and some may don’t. Knowing the side your crush belongs to will help you understand how to relate with them.

 

2.  Are You Religious?

Definitely one of the things to ask your crush. We think it is appropriate to ask this so you don’t go assuming. For example, inviting your crush to a religious music concert or sharing religious content with them would be awkward.

 

3.  Books Or Movies?

This is vital as it would help you plan dates or know what you can get as gifts.

 

4.  How Do You React When Angry?

Yes, we know you are not planning to piss your crush off, but sometimes, life happens. You’d want to know what your crush looks like when they are mad. To avoid surprises.

 

5.  What Is Your Favorite Food?

Have you talked with your crush if you don’t at least know their favorite food? Have you?

 

6.  What Is Your Choice of Pet?

It won’t be bad if you get your crush that cute little cat they’ve always wanted to have, would it?

 

7.  Do You Have Any Phobia?

Yes, you need to ask if you don’t want to make a mistake that might tick your crush off.

 

8.  Are You A Team Player Or A High-flyer?

You need to know this because if the crush blossoms into a relationship, you may need to put in more effort for the high flyer.

 

9.  Choose One Forever: Movies Or Music?

This allows you to know the preference of your crush. For example, if they are pro-music, then you know that getting a ticket for them to watch Adele perform life is more important than seeing the Avengers premiere.

 

10.  When Did You Have Your First Kiss?

The cheesy question, alright, but you have to know. You have to spice up the conversation.

 

11.  Are You A Foodie Or A Junkie?

Yet another question that asks of preference. With this question, you get to know if your first date would be at a Domino’s Pizza or Starbucks, or KFC outlet. Or if the date would be at home, with huge food bowls.

 

12.  What Weird Smell Do You Like?

There are popular ones like the smell of gas, the smell in the air after rain on parched soil, the smell of old books, etc. You’d be surprised at other weird smells you might hear from your crush. You can as well share yours if you have.

 

Questions To Ask Your Girl Crush

questions to ask your crush to see if they like you

Here are some questions to ask your girl crush:

 

1.  What Is Your Idea Of A Perfect Date?

You can bring out your pen and paper and take notes. Then, try implementing the ideas on your first date with her.

 

2.  What Is Your Relationship Dealbreaker?

It would be nice to know this so you don’t mess it up and lose her.

 

3.  Did Your Parents Ever Make You Wear Something Terrible For Prom?

This question can help you to explore how she was as a child and what her upbringing was like.

 

4.  Can You Sing?

This is one question you can ask your girl crush. It is an excellent conversation starter. If she says yes, you can tell her to sing for you. If she says she can’t and you also cannot, you two can revel in your inability. If she says no, but you can sing, You can sing for her. That might be the way to win her heart.

 

5.  What Is The Most Embarrassing Thing That Has Happened To You In Front Of A Guy You Like?

Brace yourself for this one; it is going to be hilarious. Those kinds of stories usually are. If you are feeling up for it, you can share one that has happened to you in front of a girl you like.

 

6.  When Last Did You Lie To Someone And Why?

Everyone has lied one time or the other. What could be more interesting is the reason why she lied. That is where the meat of the conversation lies.

 

7.   What Do You Think About Casual Lovemaking?

Asking her this is quite important, so you know how to manage your expectations from her.

 

8.  What Matters Most To You In A Relationship?

With this, you know the things she holds dear and cannot accommodate.

 

9.  What Do You Think About Cohabitation?

Again this will help you manage your expectations from her if you eventually end up together.

 

10.  What Is Your Greatest Achievement So Far In Life?

If you are big on purposeful living, you can ask her this.

 

11.  What Is One Thing You’d Never Try Again?

This question is perfect to know the lines she has decided never to cross.

 

Conclusion

So, now that you have a list of things to ask your crush, use them wisely. These are conversation starters that you can use depending on the situation. This set of questions will also help you get to know this person you are attracted to all the more.

Save this for later!

questions to ask your crush to see if they like you

Author: Relationship Culture

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