21 Questions to Ask Your Crush

By on January 15, 2015

Do you get butterflies in the belly every time a certain someone looks your way? Do you potentially also freeze up ever so slightly? Maybe you forget what you are about to say? Or maybe you are fully present with your guy, you just don’t really know what to ask him to have a great conversation with him and also find out as much as possible about him.

Below you will find 21 questions that work as conversation starters and that also give you an insight into your crush’s mind. You might even find out what he thinks about you whilst asking them! What’s more, you get to impress him with well thought out questions and hopefully he will ask you the same question after answering, so that he finds out about you as well.

Remember there is a certain flow to a conversations – you don’t randomly start most conversations with asking someone if they want to one day get married. Rather, let it flow and sneak in the questions whenever you can! Keep it light and keep smiling throughout.



1. What’s a Favorite Childhood Memory of Yours?

This will give you an insight into what he treasures and holds important and potentially also what shaped him to be who he is today.


2. Is There Anything That Scares You?

This can be a funny or a deep question – most of us have some irrational fears that are funny (like I still fear I will go sleepwalking as I did as a child), as well as more serious ones that we really should get rid of.


3. What’s Your Favorite City or Where Do You Think You Most Want to Live?

You can, potentially, if you live in New York for example, say something like “Is New York your favorite place to live? Do you think you’ll stay here, or would you love to move somewhere else some day?” It’s good as you figure out some of his dreams for the future, which is important if you are thinking of being in a relationship with him.

Ask him WHY he loves a certain city, favorite spots, etc. You may find similarities in what you love about a place.


Amsterdam the capital city of Netherlands


4. What Would Be Your Ideal Trip Abroad?

You can tell a lot about a person depending on how much of the world they have seen and how they would love to travel. An adventurous hike in Peru is very different from a beach vacation in Sicily.


5. What Would Be a Great Date Night / Where Would You Take a Girl if You’d Really Like to Impress Her

You will see if your sense of romance is similar and also if he ever takes you on a date, you will know how hard he is trying to impress you by comparing it to what he said.


6. What’s the Thing You Like the Most about Your Work/School?

Here you can tie it into asking about career goals and dreams for the future. Chances are you will want to date someone who is happy about their chosen profession or who is about to change into a profession they love, as they will be miserable after work every day otherwise.


7. What Do You Think the Future Will Be Like?

The Internet of Things is on its way full speed, we can soon take charter trips to the moon and life on Earth in general is changing – there’s a lot to talk about. If your crush is into tech stuff – all the better.


8. If You Could Have Three Wishes Granted, What Would They Be?

Tells you a lot about someone’s dreams and where they are at right now.



9. What’s the Most Embarrassing Thing You’ve Ever Done?

If they can’t think of anything, ask them what the cheekiest thing they’ve ever done is!


10. What Do You Think About the Concept of True Love?

Not necessarily in those words, but ask your crush if he believes in marriage, or if he prefers open relationships. A lot of people these days don’t subscribe to the idea of marrying the one person and being with them till death do them part.



11. What Are Three Things You’ve Done That You Are Really Proud of and Why?

Now you get to see if it’s helping a homeless man, or scoring high in a game of sports. A lot can be learnt from the things people are proud of.

12. What Do You Is Needed for Creating Great Relationships?

Once you know, you can give it to him!

13. What Kind of Food Do You Like?

Great to know if you are ever cooking for him, as well as if you are planning a date night.

14. What’s One Thing You Really Wanna Learn How to Do?

For some people it’s Spanish, for others it’s driving a formula one car.

15. What’s the One Thing You’d Do if You Could Change the World for the Better with a Magic Wand?

Now here’s an interesting insight into what he believes to be important for humanity and the Earth.


16. What’s Your Dream Car or Bike?

Almost all guys love talking about cars and bikes, so it’s a great way to get the conversation flowing.

17. Do You Play or Watch Any Sports?

Another one to get the conversation flowing if the guy is into his sport.

18. What’s the Craziest Thing You’ve Ever Done?

This is where you find out if he thinks it real crazy to skip one class or steal the neighbor’s car. We all have different limits in the “crazy department.”

19. Have You Read Any Book or Watched Any Movie That Truly Changed Your Life?

This question lets you find out about the things that truly move him. If he doesn’t think any books or movies were life changing, you can simply ask him

20. If You Could Be Anywhere Doing Whatever You Wanted Right Now, Where Would You Be and What Would You Do?

This gives you an insight into what his real wishes are right now.


21. What’s Your Favorite Movie Scene of All Time?

This is when you find out what makes an impression on him. The problem is if it’s James Bond throwing himself out of an airplane, you might not be able to make the same impression…



Image Source: Pinterest.com

1507760_10152392614860079_8379465670289960282_n copy 2By Maria Montgomery – Maria is a freelance writer, director and social entrepreneur. She’s also the spokesperson for The Little Angels Community Center and an avid blogger. You can find her somewhere between Cape Town, London and L.A., where you will most likely find her in the hills, looking out over the city she loves. @OhMyMontgomery



  1. Avatar


    May 27, 2016 at 2:07 pm

    Where are the questions

    • web admin

      web admin

      June 3, 2016 at 1:15 pm

      Did you try scrolling down? The questions are numbered and in bold–they should be fairly easy to see. Perhaps your computer/mobile phone browser is acting up? I just checked and everything is fine on our server, so you should be able to see it.

  2. Avatar

    Gloria Abok

    April 17, 2016 at 6:36 pm

    I need some advice please.
    My boyfriend and I have been together since one year. We’re nice to each other. We shared interests together. We listen to each other correctly. He always tell me that he missed me, and wanted to get married to me right now. Actually, he and I have the made the plan for the future and we both agreed about it. Secondly, I still don’t understand him anymore. He loved me, but whenever he missed me, he said that he wanted to have sex with me. Beside we are in different cities. I went to see him for the first time, he was madly in love with me. He hugged me so hard and said he missed me so much.

    Later, again he asked me to come see him. But since I’m a college student, things are hard for me to focus. If he needed sex, he’d sent me another women’s naked pictures saying that &even would have sex with him
    This made me so upset, if I’m at home studying or busy, he would say I’m with another guy. He just pretending only without seeing where I’m. Ithe hurts me so much. And he still don’t believe me. I don’t feel like I can trust him anymore. If he make a plan to see me tomorrow, he gives up..all the times. I’m like I’m the one who care about him. I’m still don’t understand him anymore . We’re nice since we met. But sending me another women naked pictures, and pretend that I’m with someone, doesn’t make sense to me. I don’t know what to do anymore. I’m not sure if he really love me or not. I’m not sure that put relationship is still real. Once I send him a text message, it took so long before responding. If I took so long before responding him, he pretend that I’m with someone. This hurts me so much.

    Please help me understand this type of relationship.

    • web admin

      web admin

      April 23, 2016 at 8:00 am

      It sounds like he has some serious insecurity issues. He also seems to be fairly manipulative. When you do not do what he wants, he brings up the topic of sleeping with or dating other girls. If that does not work, he accuses you of dating behind his back. Are you really sure that you want to be with him? His insecurities and controlling behaviors are unlikely to stop ever, and it will only get worse as the relationship continues. Between stress from school and trying to deal with his insecurities, it sounds like a lot of stress to take on right now. Are you sure that you want to stay with him forever?

  3. Avatar

    Charlotte Wagoner

    April 17, 2016 at 8:20 am

    So I like this guy in my school, he’s the same age as me but I have dated him in the pass and he wants to date again. The problem is he is known to be a player and says he has changed but I don’t know if I should believe him. Should I give him a chance?

    • web admin

      web admin

      April 23, 2016 at 7:28 am

      It is unlikely that he has changed this fast. What you do is up to you–if you are open to taking a chance, then go for it. You should just realize that he is most likely still a player, and he probably has not matured or changed in just the last few months. If you do date him, be careful because it probably will not end any better than last time that you dated. Good luck, Charlotte Wagoner!

  4. Avatar


    March 29, 2016 at 4:33 am

    Help!! I like his guy and he asked me out, we’ve been talking for ages and he started sending me xs and things lead on from there. but he’s nearly 18 and I’m only 15. My parents don’t know him and I know him from cadets I don’t know weather to go through with it or so no

    • web admin

      web admin

      April 4, 2016 at 7:49 am

      What you do depends on your situation. First of all, you will probably want to check with the laws in your state regarding minors and dating. You do not want to get him in trouble, and some states do not allow 15 year olds to date 18 year olds. If that is not a problem in your area, you may also want to tell your parents what is going on. They are more likely to accept him as your boyfriend if they know in advance that you want to date him. If they find out that they are sneaking behind their backs, they will not like him and will probably end the relationship. If your parents are okay with it, then go for it. If not, wait it out and try to reconnect with him when you move out in a few years. Good luck!

  5. Avatar


    February 6, 2016 at 8:51 pm

    My crush takes many hours to respond to my texts. Does that mean they’re not interested in me?

    • web admin

      web admin

      February 7, 2016 at 12:28 am

      Although it could mean that they are not interested in you, it often means that they are just busy. It is not always possible to answer back immediately, and work or school can get in the way. It is also possible that your crush is just not very good at texting, which is actually extremely common. Your crush could also be uncertain about what to say or how to keep the conversation going, which most people experience when they are talking to someone they really care about. Although it is possible that he is not interested in you, there are many other reasons why this could be happening. Keep talking to your crush, see where things go and good luck! I hope everything works out for you, CJ. Thanks for commenting!

  6. Avatar

    Mike krolls

    February 6, 2016 at 3:43 pm

    Hi. I’ve been talking to my crush everyday through text for a few months but she doesn’t seem to really ask me any questions during our conversations. I feel like I am the one who is usually continuing and initiating the conversation and getting to know her better. We’ve been out together once and it seemed like a decent vibe. But I think she has also said that she likes being single for the time being. Should I still go for it and ask her out?

    • web admin

      web admin

      February 7, 2016 at 12:10 am

      She is probably just shy and not sure of what to say. When you really like someone, it can be extremely difficult to make a move and think of new things to say. At the same time, she may also just like being single. Go ahead and ask her on a date. If she reiterates her desire to be single, point out that you guys can date without being exclusive, although you would like to have a real relationship with her if she wanted to. She seems interested in you on some level, so it would be worth the risk to just ask her out and get it over with. With any luck, you will have a cute date or a girlfriend before long. Good luck, Mike!

  7. Avatar


    February 5, 2016 at 5:58 pm

    So, I really like this guy Caden, and we’ve been getting along really well. Every day around 4:30, we email each other for like 2 hours until one of us has to go. I’m wondering what I should do, since it’s almost Valentine’s Day and I want to tell him that I like him. What do I do?

    • web admin

      web admin

      February 6, 2016 at 9:48 am

      I would just go ahead and tell him that you like him. You have been e-mailing him every day for several hours, so chances are that he is interested. That is a lot of time to invest in just talking to a friend, so chances are high that he likes you. Go ahead and tell him how you feel and see what his response is. If he says no, it would probably only be for a reason like focusing on school since he seems to be seriously interested in you.

  8. Avatar


    January 5, 2016 at 7:44 pm

    hey, i really really like this guy, Tyler, and he likes me too, he is 2 years older than me and we’ve only really talked on the internet, he wants to hang out sometime and i don’t know what to do!

    • web admin

      web admin

      January 6, 2016 at 8:06 pm

      Pick somewhere public to hang out where you can leave easily if you don’t like him as much in person. Meeting for coffee is a good idea because you can stay for as long or short of a time as you want. If you were to meet for dinner or a movie, you would have to wait for it to be over if things do not go well. Plus, meeting in a public place like a cafe is always a good idea when you just met someone online. Good luck, Gemma!

  9. Avatar

    Kellie Noall

    December 20, 2015 at 3:57 am

    So I like this guy but I can’t tell if he likes me back! We have a few classes together and he only replies to texts in those classe . Hes replied to Snaochats. My friend says he seems shy when he’s around me but I don’t see it. Please help!

    • web admin

      web admin

      December 21, 2015 at 5:02 pm

      It is possible that your friends are right, and he could be shy around you. There is no way to know if this shyness means he likes you or he just feels awkward around you. If you like him, why don’t you try talking to him more inside and outside of class? You could also ask him if he wants to hang out after school or go on a date. If he does like you, it sounds like he would be too shy to make a move, so it would probably be up to you to get the ball rolling.

  10. Avatar


    December 14, 2015 at 1:44 am

    hey, so i really dont know if i like this boy and i asked him if he likes me and he said he doesnt know either
    i really love to talk with him and his sister is my best friend but we are not in the same school so i cant see him every single day
    i really want to know if i like him or not so pleaseeeeee

    • web admin

      web admin

      December 14, 2015 at 9:26 pm

      If you are friends with his sister, why don’t you just ask her if she knows how her brother feels? For the moment, it sounds like he is not sure if he likes you or not. This could mean he is worried about the fact that you go to different schools, the fact that you are friends with his sister or (most likely) he genuinely is not sure of his feelings. Other than trying to get some information from his sister, I would probably wait before doing anything else so that he can start to sort through his feelings and decide if he would want to pursue a relationship.

    • Avatar


      December 29, 2015 at 2:17 am

      you should ask for his number so u can talk to him everyday and maybe facetime or skype. Before me and my boyfriend got together i was scared to even look at him then one day he asked me out and i said yes. You just need to follow your heart and see where it takes you. I followed my heart and now im with the best boy ever!

      • web admin

        web admin

        January 3, 2016 at 2:02 am

        That sounds like really wonderful advice, Macy. Thanks for commenting! I am sure that Giulia will appreciate it. 🙂

  11. Avatar


    November 19, 2015 at 12:24 pm

    So this guy & I have been talking for a while now. We both like each other & want to start dating but he hasn’t made a move to ask me yet. I’m afraid he is going to stop liking me or I won’t be a good girlfriend because I haven’t dated before. The only time I can sense his feelings is through text or like little gestures towards me (smiling, joking, nudging, etc.) I don’t know what to do

    • web admin

      web admin

      November 20, 2015 at 8:24 pm

      If you are worried that he will stop liking you or lose interest, why don’t you ask him out? You already know him and know that he is interested, so this is a great time for you to ask him out and see if he is genuinely interested in you. He already shows all of the other signs that he likes you, so you just have to take advantage of this time period and the signs and do something about it.

  12. Avatar


    October 31, 2015 at 5:13 am

    I need your help !! 🙁 me and this boy have been talking for ages now and we both like eachother but I don’t know if he’s a relationship kinda of boy. He has dated a girl before but he isn’t really making a move I’m not sure if he’s just going to get with me and then leave or he’s just waiting for the right time :/ HELP!!

    • web admin

      web admin

      November 2, 2015 at 2:44 pm

      If you have been dating for a long time, then right now is a good time to ask him what he wants. Even if he is not the type of guy to normally have a relationship, he might be willing to do so if he really likes you. The best way to find out what he wants is to just ask him. If you are not dating yet, then you can always just go on a few dates with him first and see where things go. It is normal not to make a relationship official until after a few dates because both people have to see if they are dating the right person first. Once you have gone on a few dates, you can always ask him if he wants to be boyfriend and girlfriend or if he is just wanting a fling. Good luck, Holly!

  13. Avatar

    Deanne Maldonado

    October 22, 2015 at 2:59 am

    I like this boy,we’ve went out two times already but I cant get over him!I text him everyday to see if he likes me but I really dont know?and his friend told me he likes another girl and she likes him?what should I do?

    • web admin

      web admin

      October 24, 2015 at 7:43 pm

      When you text him, does he text you back? Maybe you could hold off on texting him for a little bit and see if he initiates. The next time he texts you, you could also try asking him out on another date. If he says no, then you will know that things are probably over. Although he may be interested in you and the other girl, he could also be interested in just her. The only way to really see what he wants is to ask him on another date and see if he seems into it. If he is not, then you will know that it is time to move on.

  14. Avatar

    yuliana amaro

    September 24, 2015 at 2:08 am

    ummm i like someone and he likes me back but i dont know if he is lying or not what do i do

    • web admin

      web admin

      September 26, 2015 at 4:02 pm

      Why would he be lying about liking you? Unless he is a cruel or mean person, there would be no reason to lie. The main question is, is in what way does he like you. Does he like you as a friend with benefits, a girlfriend or something else? If you wanted to find out the answer to this question, you will have to either talk to him or try to go on a date. After a couple of dates, you will be able to gauge his interest level from his mannerisms and figure out what he wants from you. He may be afraid to ask you out though, so you may want to just bring up the topic yourself. Good luck, Yuliana!

      • Avatar


        October 21, 2015 at 1:46 am

        Hi, I’m having trouble with keeping friendships with my lady friends. I’m always trying to avoid getting too attached, being in my situation I know most girls don’t mean to come off as a date-able person to another girl but most of them do. Not only is it hard when you’re not necessarily out yet but having to tell all your lady friends before getting too close is draining. I’m starting to think all girls are low key lesbians, just saying. Well my question to you. How can I use these Q’s in a day to day topic, I myself and my friends Hate feeling like we’re in an interview. So what should I do?! Say?!

        • web admin

          web admin

          October 24, 2015 at 5:09 pm

          You could always make it into a game like 20 questions or something similar. Or, if you guys are bored, you could play it like a newlywed game where you both right down the answer you think the other person would say and see if you are right. As for your problem with low-key lesbians, this will not be the first time that you have that issue. Hopefully, one of your lady friends will one day actually be interested in you as more than just a friend. Don’t worry–you will find the right girl at some point.

  15. Avatar


    July 27, 2015 at 7:24 pm

    Hello, please i always have problems keeping a conversation going with my crush or any guy. How can i overcome this?

    • web admin

      web admin

      July 28, 2015 at 6:57 am

      We actually have a number of articles like this one on the website that will help you to keep the conversation going. You can always try to draw him out and get him to talk about himself. People naturally like to talk about their own interests and desires. If you want to keep the conversation going easily, talk about stories from his past, hobbies and his goals. Good luck! Let me know if you need any more help!

  16. Avatar


    July 27, 2015 at 4:37 am

    I have been looking for some good questions to ask the boy I like and I couldnt come up with any. It helped me so much I love this website. I am going to have fun seeing if these are good conversation starters 🙂

    • web admin

      web admin

      July 28, 2015 at 5:37 am

      I am glad to hear that you enjoyed this article! We have a number of similar articles that you can check out if you have time. Take a look around and let me know if you have any questions!

  17. Avatar

    Fallon Wild

    June 24, 2015 at 12:32 am

    I was wondering if you could give me some advice on my crush. He says he likes girls with authority. Well honestly, I don’t know how to be a girl with authority, he also says he hates girls who flaunt their weaknesses. I am at a loss when it comes to him, I don’t know how to become a girl with authority, please give me some advice.

    • web admin

      web admin

      June 24, 2015 at 2:42 pm

      Hmm…I think what he means is that he likes a girl with confidence. Some guys are really turned off by girls who cannot do things on their own or constantly need help. From the sound of it, you just need to be confident in who you are and have a high self-esteem. Although I would never recommend changing yourself for a guy, becoming more confident is actually a good thing, so I don’t see why not! Good luck!

  18. Avatar


    June 1, 2015 at 5:03 am

    Well, presuming that you are gay. The first thing you absolutely need to do is confirm that he is to. Most guys aren’t and you wouldn’t want to force him into anything.

    • web admin

      web admin

      June 1, 2015 at 2:07 pm

      Oh! Archer–you have to comment directly below (in the replies) to Braedyn’s comment for him to see it. The system will only notify him that someone has given him advice if you reply to his comment using the reply button. Your advice is good though–he should definitely make sure that his friend is actually gay before he does anything.

  19. Avatar


    May 11, 2015 at 6:54 pm

    Hello I’m Braedyn I do say that this did help but I’d like to know how to ask my best guy friend out without making it awkward?

    • web admin

      web admin

      May 11, 2015 at 10:14 pm

      It is really difficult to ask anyone out without being awkward. You basically just have to get over the initial awkwardness and ask your crush out. Once you have actually asked the question, the awkwardness should go away. Try asking him to go to a movie with you or to grab a cup of coffee. Both of those options should be fairly safe bets for a first date. Good luck, Braedyn!

    • Avatar


      May 13, 2015 at 8:25 pm

      Wait ur gay???


  20. Avatar


    January 30, 2015 at 1:05 pm

    it is so great it help a lot and this question r always asked!!!!!

    • web admin

      web admin

      April 14, 2015 at 10:27 pm

      I am happy to hear that this article helped you, Jenifer. If you enjoyed it, there are plenty of other topics on HerInterest that are sure to catch your eye! Thanks for stopping by!

      • Avatar


        April 18, 2016 at 1:56 pm


        I need some advice please.

        I have been with my boyfriend a year ago, and we are really in love with each other. He loves me so much and couldn’t even say one words. I love him too, and always tell him that ” i’m so lucky to have such a wonderful man like him” and ” i love him so much” about a couples of months ago, he never shares what is going wrong with him. Even from school or work, he never had the responsibility to let me hear it out from his mouth. Other times, he shout at me, another times again, he told me if he ask me something and i do not have the ability to provide, then he will go sleep with another women. I was shocked when he said that, and obviously he surely sent me the women he wanted to sleep with by pictures. They were all naked. I screamed and was schocked and couldn’t believe what he did to me. He always plan ahead for the future. he wants to marry me and have family, he wants us to live together, i accepted it too. Lastly, he pretended to me that i’m with another guy. But it’s not really true. I’m just a busy woman like him. Please help me understand this type of relationship. I don’t understand why man prefer to cheat on his girlfriend.. I’m also not sure if we are in true relationship. Because we live in a different city. Still he couldn’t how busy i am as well. What should i do? Please help me get the answer back. Please..

        • web admin

          web admin

          April 23, 2016 at 8:16 am

          It sounds like he has some anger issues and some control problems. Telling you about the other women that he wants to sleep with, accusing you of being with other guys and telling you that he could just sleep with someone else are all bad signs. It sounds like he is extremely controlling and manipulative, and these behaviors will only get worse if the relationship continues. Your best bet is to quit while you are ahead and move on. At the very least, I would deeply reconsider your decision to be in this relationship. Good luck and stay safe, Gloria!

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