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50+ Questions To Ask To Keep The Conversation With Your Crush Interesting And Fun!

50+ Questions To Ask To Keep The Conversation With Your Crush Interesting And Fun!

You know those butterflies you get in your stomach when you bump into your crush? Yes, they are the best. You can’t concentrate on anything and all you do is daydream. You find yourself wanting to know more and more about them and ask them a million questions to understand them better. And while it might be tempting to be super direct, when it comes to questions to ask your crush, you might want to pace yourself!


So how do you do it subtly? Well, we’ve made a list of questions you can ask your crush to help you get to know them better. It wouldn’t seem like you’re making too much of an effort, as these questions can very easily be a part of daily conversation and help maintain (and advance) the flow of conversation! But be prepared, some of these questions are likely to boomerang back to you! All in all, our list of things to ask your crush will make for a great way to get to know each other and build a good foundation for your future (fingers crossed) relationship! Not just that, we’ve even listed a few tips to keep the conversation flowing easily with the boy of your dreams!  


How To Keep Conversation Interesting


While talking with your crush, it is important to remember that the key is to avoid awkward pauses. Since you’re both relatively unknown to each other (at least in most cases), sometimes you’ll find that there is a lull in the conversation. Don’t worry ‘coz we’ve got you covered, sister! Here are tips to ensure that any and every conversation you have with your crush is interesting and fun!


In Person


    1. Choose The Correct Time And Place: A lot of the the awkwardness can be avoided if you’re mindful of when you’re walking up to them to start chatting. Make sure you’re not interrupting them when they’re in the middle of something, they’ll just pay less attention to you and that isn’t going to help anyone. Also, ensure that both of you have some time to spare. A conversation lasting for two minutes isn’t going to make any impact and you wouldn’t get to know them better either.

    2. Don’t Treat Them Like A Stranger: We’re not asking you to be over friendly or over familiar with them. But the key to being comfortable and holding a good conversation is to avoid treating them like a complete stranger who gets your heart to skip a beat. Instead treat him like a friend you’re catching up with! Just be calm and go with the flow!

    3. Use Your Friends To Your Advantage: What are friends for if not to help you talk to your crush? In case you two have common friends, you can always ask them about your crush’s likes, dislikes and interests. This will give you a conversation starting point and you can take it on from there. But, you don’t have to necessarily pretend to like everything they like. It’s okay, actually advisable, to be you!
      Things To Talk About With Your Crush wingman 

    4. A Little Humour Makes A Lot Of Difference: No matter what your sense of humour is like, you can always use it to score a conversation with your crush. If you two are stuck somewhere together or in a weird situation together, you can always pass a few funny comments on the same. That can work as an ice breaker!

    5. Start With Opinions: Another way to start a conversation is to ask their opinion about something. But make sure it is something of relatively less importance and ideally not about politics or religion. There is no need to open up the potential to make your first conversation your first fight. Food may be a good place to start and so is music and artists.

    6. Really Listen: People enjoy conversations where they are actually heard. So keep aside your phone for a few minutes and avoid all distractions when he is talking. You’ll understand him much better and he will actually feel appreciated. Another little trick? Listening to him carefully will give you a reference point for the next conversation. It can always start with “remember when you told me…”

    7. Leave Something For The Next Time: Always end the conversation on a cliffhanger but a good one. When you feel the conversation is going well, just end it on a happy note with something along the lines of “I gotta run now but let’s meet tomorrow and you can tell me all about your…” This way they’ll be excited to meet up with you the next time too!  



On Call


    1. Ask For His Number Calmly: Don’t make a big deal out of asking for his number or make it awkward for either of you. Casually slip it into whatever conversation you’re having at the time. Once you’ve gotten the number, don’t make a big deal about it. Continue talking as if it isn’t a big deal and you were only asking as a friend. You don’t want to creep them out. Sharing phone numbers can be a big deal so be cool about it.
      Things To Talk About With Your Crush number

    2. Start Out Low-Key: Find legit reasons to call them. A good reason to call can be to ask for help. Something like “Hey, I saw that you have the class as me, could you help me out with the notes, please?”. Sounds effortless and genuine. Once you’ve become comfortable with calling each other, you can always call them to just catch up.     

    3. Share As Many Anecdotes As You Can: A simple way to keep the conversation going is to share anecdotes. Tell him something hilarious, weird or unexpected that happened to you in the day that reminded you of him or that you couldn’t wait to share with him. This will make him feel like an important part of your life.

    4. Talk About Your Passions: Did you just see a show on Netflix that you’re totally obsessed with? Heard a new song you can’t get out of your head? Have an activity on your bucket list you’re dying to try? Tell them all about it. This way, not only are you able to have long, meaningful conversations with him, it’ll also help him open up to you and share the same with you.

    5. Use Conversation Threading: Conversation threading is quite an interesting technique of keeping the exchange going. For instance, if your crush says “I’ll be going to the USA for work,” - you can either steer the conversation towards his work or to places you’d love to see/have already visited in the USA or just travel in general. This will help you to talk for longer and discuss more than you originally intended.

    6. End It On A Good Note: Instead of an abrupt goodnight or bye, try ending the telephonic conversation on a more pleasant note. “It was so much fun to talk to you! Have a goodnight, you.” - is a much better alternative instead.
      Things To Talk About With Your Crush phone



Over Texts


    1. Mind Your Words: The risky thing about texts is that the person on the other end may have a difficult time understanding your tone. This is why it’s important to be a little mindful of your words. Maybe add a few emojis to clearly express what you’re saying?

    2. Don’t Play Games: Nobody likes mind games while texting. Just because they responded after thirty minutes does not mean you’ll respond after thirty one. A text conversation is only good when it is flowing. However, if you’re genuinely busy, don’t drop everything else to respond right away!

    3. Have A Plan And Start Simple: For the first few conversations, before you two get friendly, have a plan in place. Think about what you’re going to text and how you want the conversation to go. But also remember to make it simple. “Hey, what’s up? It was nice seeing you today!” is a much better conversation starter than “Hey, tell me everything about how your day was!” Geddit?

    4. Read Into Their Messages: While you’re literally reading their messages, do it figuratively as well. Assess how your crush is responding to your texts! If they’re replying in crisp, single word texts, it is possible that they are too busy and are just being polite. In that case, end the conversation with something simple like ‘catch you later’.
      Things To Talk About With Your Crush start

    5. Memes Are A Godsend: We need to be thankful for social media because memes are a godsend. I cannot even tell you the sheer number of conversations I’ve started thanks to a funny little meme. Just send them one with something like ‘this reminded me of you’ or ‘I couldn’t help but share this with you’ and pick up from there!   

    6. Go Off-Topic: If you feel a certain topic isn’t taking the conversation anywhere, feel free to change it. Continuing to talk about the same thing isn’t a great idea if it isn’t helping you.     



Things To Talk About With Your Crush


A Family Affair


Asking questions about his family will allow you to gain more insight into the person he is at home and the kind of family he comes from - it’s never too early to ask questions about the people he loves!


  1. Are you close to your parents?

  2. Do you have siblings?

  3. How did your parents meet?
    Things To Talk About With Your Crush family

  4. What’s your nickname at home?

  5. How often do you see your extended family? Do they all live in India?


Interests And Hobbies


Figuring out what his hobbies are will allow you to see what kind of things you two have in common! Plus, it’s a light-hearted way of finding out more about him and the stuff that makes him happy.


  1. What’s your favourite quote from a movie or a TV show?

  2. Are you into sports?

  3. What kind of music do you like?
    Things To Talk About With Your Crush music

  4. What’s the last book you read and were blown away by?

  5. When’s your birthday? What do you know about your sun sign?

  6. If there was no money involved, what is the one thing you’d love to spend your time doing?

  7. What kind of movies do you like?

  8. Who is your favourite actor/actress and why?
    Things To Talk About With Your Crush movies

  9. What do you love to do in your free time?

  10. Do you like sports? Which is your favourite one?

  11. What is your guilty pleasure?


Love Is In The Air


Some of these questions are the ones you will be dying to know the answers to, because they are the ones that will help you figure out if you should be looking at a relationship or not and what his past relationships have been like. However, don’t indulge too much in the information you receive about the past - look forward instead, and appreciate that he does have a romantic side to him!


  1. What’s the most romantic thing you’ve ever done?

  2. Why did you and your ex break up?

  3. Have you ever been in love?
    Things To Talk About With Your Crush love

  4. What did you think of me the first time we met?

  5. What’s your idea of a perfect date night?

  6. Do you believe in the idea of soul mates?


Dreams And Desires


These questions are great to see what kind of person your potential beau wants to become. It’s a nice way to see what his ambitions and aspirations are, and also to see if you want similar things out of life!


  1. If you could be anyone for a day, who would it be and why?

  2. What’s the one thing you want to achieve in life?

  3. If you could sum up your philosophy/mantra for life in one sentence, what would it be?

  4. If you could live in the city of your choice, where would it be?
    Things To Talk About With Your Crush city

  5. If a genie came to you and granted you three wishes, what would you ask for?

  6. If you could just take six months off from your daily routine, what would you do in that time?

  7. What’s the accomplishment you’re most proud of?


Memory Box


Getting to know someone’s past means them having to dig through their mind to answer your questions - it will act as a bonding exercise for both of you and establish a certain level of trust!


  1. Where did you grow up?

  2. Are you still in touch with a lot of your school friends?

  3. What’s your most vivid/first memory as a child?

  4. What’s the naughtiest/most embarrassing thing you did as a kid?
    Things To Talk About With Your Crush naughty kids

  5. Do you ever wish you had done something differently?

  6. If you could turn back time and go back to one phase of your life, what would that phase be?


Daily Dilemmas


Ranging from the mundane to the existential - questions like these force your crush to think and respond. It will allow you to get some insight into the way his brain thinks and will act as a good conversation starter for more abstract discussions, instead of having to talk about the tangible everyday life!  


  1. Do you like dogs or cats?

  2. Would you rather be rich or famous?

  3. Do you think it’s better to beg for forgiveness or ask for permission?

  4. If you won the lottery, what’s the first thing you would do with the money?
    mehendi games tambola

  5. What do you think the future is going to be like?

  6. Chicken or the egg, which one do you really think came first?


Flirty Things To Text


If you think your crush is even a little bit into you, you can always flirt. Don’t worry about being the first one to make a move. So here are some cute things to text your crush to make him smile.


  1. I don’t have anything to say but I really wanted to talk to you, so… Hey!

  2. My pet wanted you to know that he’s missing you!

  3. If you want to make a move on me, now would be a perfectly good time to do that.

  4.  Hey stranger, can you stop being a stranger?
    Things To Talk About With Your Crush flirting

  5. You’ve been on my mind a lot today and it’s only 10 am!

  6. Hey, I’ve been having hiccups. Can you stop thinking about me so much?


Work Work Work


Work is an important part of everyone’s life. After all, you spend half of your day at work/college. So to get to know them, it’s always a good idea to ask them about their work. They’ll also be excited to tell you about the same!


  1. Is your job mentally satisfying?

  2. What are the people at your workplace like?

  3. What did you like studying the most? Is that linked to your job?
    Things To Talk About With Your Crush studying

  4. If not this, what else can you see yourself doing?

  5. What are your long term plans, career wise?


The Importance Of Boundaries


While you may be really into a guy and sure that they’re the one for you, it is important to respect the boundaries they’ve set as well. Sending your crush flirty texts or starting up a conversation in the corridor with them is fine as long as they’re cool with it. But it is also important for you to be mindful of the non-verbal cues and make sure that you’re not intruding on their private space or making them uncomfortable. Also, if they’ve clearly told you that they’re not interested in you romantically and would only like to be friends, then do not pursue them relentlessly hoping they’d change their mind because consent matters. Having a crush may be a heady feeling for you but for them, having a stalker (for the lack of a milder word), is no breeze! 


GIFs: Giphy


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Published on Jul 15, 2015
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