335 Deep Personal Questions to Ask Your Crush

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Have you fallen for someone? Great!

So, you have a crush on this guy or girl, but you don’t know much about them. You don’t know if they are already in a relationship, what were their past relationships like, what they like, what they don’t like, what are their thoughts about their future, what are their career goals, and the list goes on and on. Right?

In that case, the best thing you can do is to ask them directly. This will give you an idea about how this person is actually, their dreams and aspirations, and the most important part – what they think about you.

You know, even after five years of marriage, sometimes, I feel like I still don’t know my husband properly! Yes. After all, there is no end to knowing someone. And the more you get to know someone, the more you fall for them.

And who knows, in the process of knowing your crush, they may fall for you too!

Now, are you a shy person and don’t feel like asking questions to your crush when they are sitting right in front of you?

Well, you can send these questions as texts too!

Here comes the most important question, do you even know what to ask?

To help you with that, I have come up with some deeply personal questions to ask your crush. The questions range from random and career-related to love-related and beliefs-related – everything!

Deeply Personal Questions to Ask Your Crush

When I talk about knowing someone well, there are so many questions that you can ask. And once you start asking questions to your crush, you will feel like there is no end to it!

So without further ado, let’s get started!

Personal Questions to Ask Your Crush About Their Past

When you are getting to know a person, you will feel the urge to know about their past too. And that leads to this section of questions!

Are you comfortable talking about your past?

What is the best memory you have of your past?

What is the worst memory you have of your past?

How was your childhood? I give you four words to describe it

How many dates have you been to till the present?

Are you okay with your past?

If you were given a choice to change something in your past or let your life be how it is, which option would you choose?

Were you fond of anyone in your past?

Was there anyone you were in love with in your life?

What is the best memory you have with your crush?

Have you ever wanted to be your ex forever?

Have you ever thought of breaking up with your ex while in a relationship?

How was your previous relationship experience?

What is the stupidest thing you have done on your date?

Have you ever felt embarrassed on a date?

Did you ever make your ex feel embarrassed because of you?

How was your life post-breakup?

How did you deal with your breakup?

Have you been able to move on, or do you still have feelings for your ex?

What did you fear the most when you were a child?

Is there anyone that you admired the most in your childhood?

Did you have any childhood crush?

Did you ever have a crush on your school teacher?

Who was your favorite teacher?

What was your favorite subject in school?

How good of a student was you in school? If I ask you to give yourself a rating between 1 and 10, what would you rate yourself?

What is the biggest mistake you have made in love?

Did you have any family traditions that you followed when you were a child, no matter what?

Who is the one person that you respected the most when you were in school? Is there any specific reason?

In your childhood days, when you were asked what would you become when you grew up, what was your answer?

What were your dreams when you were a kid?

What is your hard-earned lesson from your previous relationship?

What is the name of your first ever crush?

What is the name of your first ever boyfriend or girlfriend?

What is the one thing that you did while being in your first relationship that you now think was one of the stupidest acts of your life?

Did you like going to school?

How were your college days?

You have been to a lot of places during your holidays. Which one is the best according to you?

What is the scariest relationship experience you have, if any?

What was the longest time you have been in a relationship?

What was the shortest time you have been in a relationship?

Which is your best relationship to date?

Is there any of your exes that you still have feelings for?

Have you ever given up an opportunity and regretted it a lot afterward?

What is the craziest thing you have done to impress someone? Were you successful in doing so?

How much have you changed since your childhood?

Is there any decision that you made during growing up that is the most rebellious one?

How was your equation with your parents during your childhood?

Which phase in your life is the best one till now?

Personal Questions to Ask Your Crush About Love

So, you want to be in a romantic relationship with your crush, right?

But do you know what their thoughts are on love? Or if they are ready to be in a new relationship?

Ask them these questions!

How old were you when you lost your virginity?

Do you think one-sided love turns into mutual love after a time?

If you get the chance, would you choose to date your ex again?

Who do you think you had a greater chance to click with of your exes?

How deep were you invested in your past relationships?

Have you ever met someone and thought that “s/he is the one?”

What in a girl makes your turn on?

Has it ever happened to you that you had just heard the voice of someone, and you fell for them?

Does sexy voice work for you?

Can you describe how you get turned on non-physically?

Have you ever broken up with your ex and then regretted it a lot?

What qualities do you want your partner to have?

What, according to you, is the best trait your partner can have?

What are your thoughts on dating someone who is still not completely over their ex?

Have you ever been in a relationship just for the physical aspect of it?

Have you ever regretted being in a relationship with someone?

Do you think that if love is true, there has to be a sacrifice?

How are you as a boyfriend or girlfriend?

How much do you rate yourself on a scale of one to ten as a partner?

What is the best kissing memory you have?

With whom do you have the best kissing memory?

With whom did you want to spend the rest of your life, but it didn’t work out?

How would your date be like if you had only $20 in your pocket?

How old were you when you had your first kiss?

When was it that you had your first romantic relationship?

What is the longest time you have taken to forget someone?

What do you fear the most about being in a relationship?

What is your dream date like?

Would you like it if your date made the first move?

How would you feel if your date never called you back after your first date? What would you think went wrong?

Do you believe in soulmates?

What is the weirdest place that you want to make love?

What is the craziest place you want to kiss your partner?

Are you more of a butt person or a boobs person?

Do you think you will realize that your date is “the one” the moment you meet them?

What makes you feel attracted to someone?

Do you like girls with beauty or girls with brains?

Do you prefer sex on the beach? What are your thoughts on it?

Do you prefer casual hookups or serious relationships?

Has it ever happened to you that you have fallen for someone on a blind date?

Have you ever been on a blind date? How was it?

Have you ever created a profile on a matrimonial website?

Have you ever joined any groups or forums on social media for a romantic relationship?

Have you ever kissed on your first date?

Have you ever done anything stupid on your blind date just to make your date go away?

Have you ever made a fool of yourself in front of your date?

Have you ever thought of getting intimate with someone just after meeting them?

Have you ever felt only the physical attraction toward someone without any feelings?

Have you ever fallen for someone without knowing that they have been taken?

Have you ever had a one-night stand with someone already taken?

What are your thoughts on a threesome?

Have you ever watched videos of people of the same gender having sex? How did you feel? Did it excite you?

What is the first feeling of love, according to you?

Have you ever been cheated on by your partner?

Have you ever ditched your partner for someone else?

Have you ever thought of cheating on your partner while you are already in a relationship?

How must trustworthy should your partner be according to you? Do you want them to let you look at their phone?

How important is sex in a relationship, according to you?

Do you think there can be no platonic relationship?

Do you think you can give up some of your bad habits for the sake of your love? Name three bad habits

What is the one thing that can make you fall for someone if you see them doing that?

How did you feel when you said your first “I love you” to someone? Were you nervous?

What does your dream proposal look like?

You May Also Read: 234 Deep Relationship Questions to Ask Your Boyfriend

Questions to Ask Your Crush About Their Personal Beliefs

If you want to be with a person for the rest of your life, you need to know about their beliefs, values, and principles. After all, you don’t want to end up with someone who has issues with your principles, right?

You need all these personal questions to ask your crush about their beliefs!

What motivates you to achieve your goals in life?

Would you like to have a happy life on earth, or would you like to have a happy afterlife if given a choice?

Do you believe there really is a divine power that controls the universe?

Do you believe in Karma?

Do you believe in forgiveness? For example, would you forgive someone who has done some of the worse things to you?

Would you give a second chance to someone who has done bad to you? Do you think a second chance should be given to everyone no matter what they did to you?

What, according to you, is the meaning of life?

Is there something that adds meaning to your life?

Do you believe that there is really heaven and hell?

How much faith do you have in astrology? Do you really believe it?

What principles do you have in life?

Do you always follow your principles?

Do you believe in always speaking the truth, or do you think it is okay to lie sometimes?

Has it ever happened to you that you said a lie because you were extremely afraid to tell the truth?

Is there anything that made you change your views on life?

Do you like to live life as it comes, or do you like to plan everything beforehand?

Do you think God has made someone, especially for you?

What is your life’s philosophy?

What kind of life do you expect to have after your death?

Do you think the afterlife is real?

What are the four things that you cannot live without?

Do you believe in your religion?

Do you believe in some other religion?

Do you think one should obey one’s religion?

What do you mean by spirituality?

What, according to you, is fate?

What-If Questions to Ask Your Crush

Give your crush these what-if scenarios and see what they reply! This will help you a lot to know about them.

What would you choose if you were to choose between day and night and stay like that for the rest of your life?

What would you choose if you had the option to be Superman or Batman?

If you could change one bad habit of yours, what would you change?

What would you choose if you could do one job for the rest of your life?

If you could have one relationship in your whole life, with whom would you like to spend the rest of your life?

What would you choose if you could swap one of your bad habits with a good one?

If you could permanently change the color of your eyes, would you go for it?

If you could be a genie or a wizard, which one would you be?

What would you choose if you could live for one season as long as you are alive?

Who would you choose if you had to choose between your parents or your siblings?

If you had the power to grant the wish of someone, whom would you choose?

Would you like to know if there was a way to find out the day of your death?

If you could live only on drinks, which one drink would you choose?

What would it be if there was one incident in your past that you could go back in time and change?

If given a chance, would you like to time travel, or would you like to get the power of invisibility?

If you could change one part of your body for the rest of your life, which part would it be?

What would it be if you got the power to keep only one part of your body not age at all?

What would you say if you could go to your past and say something to yourself?

What would you choose if you were given the option to choose between hell with your close ones or heaven with your foes?

If you had to post one of your dirty secrets on social media, what would you post?

If you were to choose between a loyal but average-looking partner or a super hot but disloyal partner, which one would you go for?

If you were to choose between one partner for the rest of your life or one new and beautiful partner every day for the rest of your life, what would you go for?

What would you do if you had the power to redo one of the incidents in your past?

What would you choose if you could choose between the partner of your dreams or a rich partner?

If you could choose your wedding decoration – no matter the cost- what would it look like?

What would be your choice if you could choose your dream honeymoon destination without paying money?

If you could swap your siblings with someone else, would you go for it?

If you wrote a song about your past relationships, who would you like to listen to it first?

If your life was a movie, what would be the title of it?

If your life was a dream, would you ever like to return to reality?

If your life was a song, what kind of song would it be?

What would be its title if you could write a book on your life?

If you get the chance to appear in one of your favorite reality shows, which one would it be?

Personal Questions to Ask Your Crush About Their Last Time

These questions are super exciting and interesting! Don’t believe me?

Read them for yourself!

When was the last time you had a relationship with someone?

When was the last time you kissed someone of the opposite sex?

When was the last time you lied to someone to impress them?

When was the last time you had sex?

When was the last time you got cheated on?

When was the last time you cheated on someone?

When was the last time you went on a date?

When was the last time you went on a blind date?

When was the last time you dropped someone at their home?

When was the last time you took the opportunity of impressing someone without even thinking twice?

When was the last time you cried?

When was the last time you felt heartbroken, and for what reason?

When was the last time you traveled to a different country?

When was the last time you believed someone but later found out that they were lying?

When was the last time you spent the night with someone else?

When was the last time you hooked up?

When was the last time you got drunk and did things reminding you that only embarrassed you?

When was the last time you wanted to have sex with someone, but things didn’t work out?

When was the last time you laughed hard because of some embarrassing situation?

When was the last time you listened to your friends and did something miserable?

When was the last time you trusted someone?

When was the last time you went to a party?

When was the last time you helped someone?

When was the last time you cried for the person you loved?

When was the last time you farted?

When was the last time you tried something that you didn’t want to at first but then did and enjoyed a lot?

When was the last time you watched a sad movie that made you cry?

When was the last time you had second thoughts about your career?

When was the last time you asked someone a favor only to get rejected?

When was the last time you went to the theatre to watch a movie and with whom?

Personal Questions to Ask Your Crush About Their Career

A career is one of the essential aspects of a person’s life. Don’t you agree?

And so, you need to ask your crush the following questions about their career.

How close are you to your colleagues?

Do you consider your colleagues your friends?

Are you happy with the salary you are getting?

Do you think you are getting the right salary, or do you think you deserve more?

Do you want to learn new skills so that you can upgrade yourself, or are you happy with the skills you already have?

How good are you at salary negotiation?

Do you think you will get promoted this year?

Are you dependent on anyone at work?

How much do you like your job? Are you happy with it?

Do you love your job more or your workplace more?

Has it ever happened to you that you rejected a high-paying job offer just because you didn’t want to go to a new workplace?

Has it ever happened to you that you rejected a great job offer and regretted it a lot later?

Are you happy with all the decisions you have made so far related to your career?

If your job requires you to go to a place far from your house and work from there, will you be okay with that?

If your job requires you to learn new skills, will you do that, or will you look for another job that doesn’t require you to upgrade your skills?

Do you wish to stay in the same job for the next five years, or would you like to change?

Where do you see yourself in the next six years?

What are your career goals for this year?

What is the worst experience that you have had at your workplace?

Are you a workaholic?

How serious are you at work?

Do you trust your colleagues?

Has it ever happened to you that you did some exceptional job at your work, and someone else took the credit?

Have you ever felt betrayed by any of your colleagues?

Do you become another person when you are at work?

How far are you willing to travel for work?

What do you think are the top four qualities that make a boss good?

What lesson have you learned from your first job?

How many jobs have you changed to date?

What is the biggest lesson you have learned from all your jobs to date?

If I ask you for career advice, what advice would you give me?

What do you think about freelance?

Do you think one should have a part-time job apart from a full-time job?

What, according to you, is job satisfaction?

Are you happy doing your current job?

Also Read: 10 Thoughtful Questions to Ask Your Crush

Random Personal Questions to Ask Your Crush

When you want to know the person you love, there are so many questions that come to your mind, right?

So, here are some random questions that you may want the answers to!

When you were a kid, which cartoon did you like the most?

Do you prefer having a partner but no baby or baby but no partner?

If someone wants to see you happy, what are the four things that they need to do?

What comes first in your life: your family, love, or career?

Do you think that in order to fall in love, the person has to be right, or the time has to be right?

Do you write journals?

Do you believe in god?

What are the things that you look for in a relationship?

Do you have any setup in mind that, according to you, is the perfect kind of date?

What do you generally like to do when you are on a date?

Is there any book that inspired you the most?

Who is your biggest inspiration in life?

Whenever you have any issues in life, who is the one person that you go to for advice?

Is there anyone special in your life?

Have you experienced something that has changed your life forever?

Are you a night or a morning person?

How important is social media for you?

Do you post all the events in your life – no matter how big or small they are – on social media?

Do you share your love life with your parents?

Have you ever taken your partner to your home?

Have you ever gone to any of your partner’s homes?

What are your thoughts about infidelity?

What, according to you, is the greatest invention by humans?

What is your favorite body part?

Have you ever fantasized about someone you hate in real life?

Have you ever fantasized about someone you shouldn’t have?

What is one important lesson that life has taught you?

Have you ever fallen for your teacher in college?

Do you think telepathy works?

What is the one thing that you are manifesting right now?

Have you fallen for someone recently?

Is there anyone that you find attractive?

Have you ever broken the law? What did you do?

Have you ever gone to jail?

Do you follow the law strictly, or are you casual about it?

Who is your favorite colleague? And why?

Is there anyone in your friend circle that you share a special bond with?

Do you like beaches or mountains more?

What, according to you, is the perfect kind of vacation?

Do you like to travel? How much?

What would you say if I gave you five words to describe yourself?

Do you believe in mythology?

Are you a religious person?

Are you into giving or taking?

When you were a kid, did you ever wish you had superpowers?

If God gave you a superpower, what would you ask for?

Are you more of a DC person or an Avengers person?

Who is your favorite Marvel superhero? What do you like the most about them?

Who is your favorite family member, and why?

Have you ever lied to your parents about something and then got caught?

What is the biggest punishment you received from your parents when you were a kid?

Do you have any secret hobbies? Why is that a secret?

What is the first feeling that you get when you meet someone new?

Are you good at making friends? How good?

What was your favorite subject in school?

In which subject did you use to get the highest marks in school?

Are you fonder of your mom or dad?

What would it be if you were to choose the one place on earth where you could live the rest of your life?

Do you believe in astrology?

If you find out that you are wrong and that the mistake is yours, do you accept it, or do you keep quiet?

What are your passions in life?

Have you ever fallen for the wrong person?

Have you ever found out that your partner had been cheating on you?

If your partner cheats on you with your best friend, will you ever be able to forgive them, forgetting everything they did to you?

Do you take revenge if someone does bad to you, or do you leave it to karma?

What is the most embarrassing memory you have of yourself in school?

Has it ever happened that you ate someone else’s tiffin in school?

What do you generally do when you find yourself in a stressful situation?

Do you stress out often, or are you more of a cool person?

Do you remember the first movie that you ever watched in a theatre?

Have you ever slept outdoors?

Have you ever taken a trip with your friends?

What is the most memorable trip you have had to date?

Have you ever planned a surprise for someone?

Have you ever got a big surprise from someone?

Is there anything that you are proud of yourself?

Do you want to own a house someday and have a family?

Is there anyone whose influence is on you?

Are you a bathroom singer? What is your favorite song for your shower time?

Do you wish to have your own car someday?

Do you like cars?

Are you a movie buff?

Do you like to read books?

Is there any character from any movie that you find similarities with?

Is there any musical instrument you know how to play and are pretty good at?

Have you ever felt frustrated because of your career?

What would you choose if you were a supervillain and got to choose your powers?

Do you think of any qualities a woman should have if they wanted to be a perfect wife?

What kind of partner do you prefer? Do you have anything in mind?

Do you know how to cook? How good are your culinary skills?

Is there any novel that inspires you?

Can you remember the most embarrassing incident of your life?

What, according to you, is the definition of a perfect life?

What fashion item, according to you, makes a woman prettier?

What is that one dream that you want to make a reality?

How would you live your life when you know that you have only two days to live?

Do you like to listen to the advice of experienced people, or do you like to figure everything out on your own?

What is your all-time motivational quote?

What is the one movie that inspired you the most?

Conclusion

Did I miss any personal questions to ask your crush?

Feel free to let me know in the comments!