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


    August 5, 2019 at 5:17 pm

    I really like this guy in my friend group and he knows I think he’s cute but I just met him a few days ago what do i do?

    • web admin

      web admin

      August 6, 2019 at 12:42 pm

      You think he is attractive and that has other qualities that you appreciate. You met him recently, and it is perfectly acceptable for you to reach out to him. Make a decision about what you want for the future of this relationship. Speak with him about your thoughts and feelings. Give him an opportunity to share himself with you as well. Have a great day, Leah!

  2. Avatar


    January 6, 2018 at 3:59 pm

    I need help! I really like this guy in my PE class and he is in our friend group but we don’t talk too much. People say he likes me and I’ve been getting mixed messages from him. Im not sure what I should do!! Should i just go for it and ask him out or should I wait to see what he does? I don’t want to wait too long though because then if he does like me, he might lose interest and like someone else. HELP!!!

    • web admin

      web admin

      January 6, 2018 at 6:41 pm

      Take this time to determine what you want for the future of this relationship. Speak directly and honestly with him about your thoughts and feelings. Give him an opportunity to share himself with you as well. Have a great day, Duck!

    • Avatar

      terri caylow

      September 1, 2018 at 5:21 pm

      i would say to wait for a bit like you have and then once you know more about each other then go for it cuz you want to know more about each other first before you jump right in becuz you might like him and he might not like you then yo u would be embarrising your self x

      • web admin

        web admin

        September 1, 2018 at 9:05 pm

        That sounds like good advice. Thanks for commenting, Terri Caylow!

  3. Avatar


    December 23, 2017 at 9:57 am

    I really like my best guy friend, and I don’t know what to do. My friend told me he likes me, but I can’t always trust that because last time it just ended up really bad. I’ve been in bad relationships before and I’m scared to enter a new one only for it to end up bad again. The other problem I have with liking him is that he can’t date, his parents don’t trust him and he has to hide that he has certain items from them that are the simplest things like a hat or something. They’re really overprotective of him and I don’t want to lose their trust. I’ve done stupid things that I could have gotten in trouble for, which I haven’t gotten in trouble for. I really do love him, but I don’t know if it’s even worth it at all anymore..

    • web admin

      web admin

      December 23, 2017 at 7:13 pm

      Take this time to determine what you want with this relationship. Speak directly and honestly with him about your thoughts and feelings. Give him an opportunity to share himself with you as well. Do now allow negative experiences and previous relationships prevent you from developing a new relationship. Have a great day, Lacey!

  4. Avatar

    John Brandon

    November 5, 2017 at 1:16 pm

    this girl is sending me mixed messages, how do I know if she wants to be more then friends without ruining it all?

    • web admin

      web admin

      November 5, 2017 at 8:40 pm

      Take this time to determine what you want for your future. Nourish this relationship as a friend until you are certain that she is interested in developing a stronger relationship with you. When you feel more confident that he is interested in doing so, then speak directly and honestly with her about your thoughts and feelings. Spend additional time with her in person, as this will strengthen your mutual connections. Have a great day, John!

  5. Avatar


    October 14, 2017 at 6:51 pm

    I like this guy in my grade not sure if he likes me by i like him and he kinda shows signs he likes me but I’m afraid to ask him cause we are good friend *Need help*

    • web admin

      web admin

      October 15, 2017 at 7:51 pm

      Take this time to determine what you want for your future. If you want to develop a relationship with him, then speak directly and honesty with him about your thoughts and feelings. Attempt to spend additional time with him. Give him a chance to share himself with you as well. Have a great day, Savannah!

  6. Avatar


    July 18, 2017 at 2:23 pm

    My guy Lives in america!

    • web admin

      web admin

      July 18, 2017 at 3:18 pm

      Thank you for sharing your thoughts. Have a great day, Winner!

  7. Avatar


    July 5, 2017 at 12:23 pm

    i have a crush on a boy that i have know for years,and now he is in a different country. i don’t know how to tell him i do love him.

    • web admin

      web admin

      July 5, 2017 at 1:51 pm

      If you want to reach out to him, then do so. Speak directly and honestly with him about your thoughts and feelings. This will give him the opportunity to share his thoughts and feelings with you as well. If your relationship can not function due to long distance, then simply remain friends with him. If the two of you are able to develop a relationship together, then make it happen. Have a great day, The!

  8. Avatar


    May 4, 2017 at 2:21 pm

    I’m dating this one kid in my grade but I’m starting to have feelings for another kid who I have a lot more in common with. My boyfriend won’t answer my texts and I wanna tell him about all this but I just don’t know what to say. I really like the other kid but I also really like my boyfriend. But my friend has been here for me more than my boyfriend has. What do I do?!!! Please help me!!!!!

    • web admin

      web admin

      May 6, 2017 at 1:21 pm

      It is not a good idea to try to date someone else or entertain feelings for someone else when you are in a relationship, so we will focus on the first problem: your boyfriend. From the sound of it,you feel like you do not have a lot in common and he is not always there for you in a relationship. You have two possible solutions. One is to tell him how you feel and talk about ways that he can change. Your other option is to just break up with him if you don’t think that real change is possible. Once you decide between these two options, you will then be in a better place to decide if you can or will date the other guy. Base your current relationship decision on just your relationship because a) it is more fair to your current boyfriend and b) it makes your decisions easier to make.

  9. Avatar


    February 24, 2017 at 11:00 pm

    I like this guy and he knows i like him but he is flirty with everyone and i asked him if he cares about me and he said yes and we text and talk and he hugs me when we see each other is he worth it?

    • web admin

      web admin

      February 26, 2017 at 12:32 pm

      He may be worth it. As the two of you are not in a relationship at this time, there is nothing stopping him from speaking with other people. If you want to become closer with him, then spend additional time with him. Learn about his thoughts and feelings and share yourself with him as well. This will give you the best chance of developing a relationship with him. Best of luck, Vanessa!

  10. Avatar


    February 13, 2017 at 5:21 am

    he know i love him but is taken …..what to do , should i leave him?

    • web admin

      web admin

      February 13, 2017 at 10:03 am

      If either of you are in a relationship, then do not seek a relationship. No good things can come from harming someone else. Have a good day, Lis.

  11. Avatar


    November 6, 2016 at 12:16 pm

    im a girl and I like this guy, but don’t know how we would hang out all the time. is he worth it?

    • web admin

      web admin

      November 7, 2016 at 3:13 pm

      It is up to you to determine if he is worth it. Take this time to look inward and decide what course of action that you want to take. Whatever you decide is the right decision for you to make. If you want to speak with him more so the two of you can become closer, then do so. If you want to take this time to get to know yourself and your needs better, then that is a wise decision as well. Have great day, Kylie!

  12. Avatar

    jasmin ilani

    November 5, 2016 at 8:50 pm

    Hey, so I’ve been dating the same guy for 30 years. So he keeps telling me that he’s visiting his sister like at least 20 times a weeks, sometimes daily. I looked on Facebook and she actually lives in Alaska. I wanna meet her, but he keeps giving me excuses to why I can’t like, “Her goldfish is drowning and it’s too stressful for a lot of people to be at her house all at once.” But a goldfish can only drown so many times… Anyways, I’ve thought long and hard about this and the most rational reason I can think of is that he has a teleportation device and that is how he can visit his sister so often since I live in Hollywood not in California, in Florida.SO HE IS HIDING IT FROM ME. DO you know how useful this could be? I’m really pooped because he will not show me and I want to use it. How do bring this up or ask him because I don’t want him to know that I Facebook stalked him or I will get a hard spanking. Please, please help me. I need answers…soon.

    • web admin

      web admin

      November 7, 2016 at 2:53 pm

      It seems as though you are in an unusual relationship that may or may not involve him treating you without respect. There is no reason for him to have a problem with you going through his Facebook, and there is no reason for your action to have an abusive consequence. If he is telling you that he is visiting his sister who lives across the country, then he is lying. If he is saying that her fish is drowning, then he is making a joke or lying. You should speak with him directly and honestly about your feelings. There may be something not right in your relationship. Take this time look determine what is going on and take action from that point. Best of luck, Jasmin!

  13. Avatar


    November 3, 2016 at 7:29 pm

    So i like this guy but he is dating my friend i feel like we have a lot in common but we only just started talking. its sometimes a little awkward around us and i dont know if he likes me. please help.

    • web admin

      web admin

      November 4, 2016 at 6:29 pm

      As he is dating your friend, you only have one option. Support their relationship and remain his friend. There is no reason for you to ignore him, but if you attempt to break up their relationship, then only negative fruits will come to you. You may lose your friend, you may have other social side effects, and your relationship with him may be poisoned from the start. If the two of them break up naturally, then, in time, you can seek to develop a relationship with him. For now, support them and be kind. Remain mindful, Nashaly!

  14. Avatar

    Emma Lemaitre

    October 12, 2016 at 1:18 am

    Having trouble getting the guy I like to notice. We sc each other a lot but I am scared of making it awkward and have no clue what to ask him to get to know him better. Thoughts?

    • web admin

      web admin

      October 12, 2016 at 11:30 am

      Talk to him! You will never know if he likes you back or not if you do not take the risk of talking to him. At the very least, start saying hello when you walk by him. That way, he will have an opening to keep the conversation going if he does like you back. It might be nerve-wracking, but it is better than spending your entire life wondering what could have been possible. Good luck, Emma Lemaitre!

  15. Avatar

    Just That One Chick

    October 4, 2016 at 7:45 pm

    So I have a crush on a sophomore, everybody thinks that it’s REALLY cute because I’m in eighth grade. He knows that I like him and he’s fine with me liking him, but I want to tell him my actual feelings. I’ve written down so many letters and either burned them or threw them away. I’ve kept one that I really like. We have a marching band contest this Saturday and I was wondering if I should give it to him then? It’s basically asking if he would like to get to know me better and saying that I would like to get to know him better. Is that okay? I told him (In the note) that it was his choice whether or not to get to know each other better. Is that okay or should I take out some things or add things? Help! I’m freaking out!!! AHH!!

    • web admin

      web admin

      October 5, 2016 at 9:24 am

      If he knows that you like him, then you don’t really have to do anything else–he can always make a move if he is interested. If you want to just tell him that you want to get to know him better, I don’t see anything wrong with that. He does know that you like him already though, so it may not be necessary. After all, if he is interested, he already knows that you would like to get to know him better and maybe have something more. Good luck!

  16. Avatar


    August 24, 2016 at 10:58 pm

    Ok well I still like my ex and he has told me that he still likes me I do not know what to ask him to see if he would like to get back together and I really still lovenhim what should I ask him to see if he wants to get back together

    • web admin

      web admin

      August 26, 2016 at 8:50 am

      You never know what the answer will be unless you ask. He did say that he still likes you, so he may be interested in dating again. What was the reason that you guys broke up? Whether he will want to get back together will most likely depend on why you guys broke up and what he wants out of his life now. I would just tell him how you feel. At the very least, you will get closure by learning that nothing is possible. And in the best case scenario, you will get to be with your ex again. Good luck, Serenity!

  17. Avatar


    July 31, 2016 at 5:10 pm

    Hi. So I’m just starting high school, and there’s this guy I have had a crush on since 7th grade. I got his sc and number, and we have been talking, but we aren’t really going anywhere. Plus; I am an extremely shy girl and I can’t talk to him in real life. Like the only time we talked was over FaceTime ONCE and that doesn’t really count. Can you give me some advice on what to do now? We know each other pretty well and I’m running out of things to talk to him about

    • web admin

      web admin

      July 31, 2016 at 6:50 pm

      If you want to develop a relationship with him, then you will need to take the first step. Jump out from your shyness and text him your honest feelings for him. Tell him that you want to spend some time with him to get to know him. Sometimes nature walks are the best date for shy people. Sometimes a quiet cafe can be a great place. Figure out what you want for your date and ask him out.

  18. Avatar


    June 17, 2016 at 9:09 pm

    So I’m a guy but I noticed that you actually talk to the people that need help. And I need it bad. So I told my crush upfront that I liked her and its kinda been akward. Now if I try to text or snapchat her she looks at it but never responds. What can I do to have her talk to me again.

    • web admin

      web admin

      June 18, 2016 at 3:00 pm

      Sometimes it is difficult for people when receiving the news that they have a crush. A common reaction is for people to need to take some time to themselves after being spoken to. Your crush may also be in a relationship, spending some time on herself, or maybe thinking about what a relationship with you would look like.

      For now, give her time to think about what you said. Instead of texting or messaging her over the next few days, allow her to absorb this new information. I would give her three days to allow her mind to adjust to the new information. At the end of those three days, treat her just like you did before you told her how you felt. Likely the relationship will return to normal, but the seed of a relationship has been planted. Good things come to those who wait.

    • Avatar

      Patrick bolt

      July 19, 2016 at 3:40 am

      Keep it cool say you want to be friends and start to flare things up a bit in the future it just takes all a bit of time

      • web admin

        web admin

        July 19, 2016 at 3:36 pm

        Tank you for the insight. Often times it is helpful to be patient and show your potential partner that you are caring and relationship material.

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