How to start a conversation with your crush without it being awkward

This article was co-authored by Eddy Baller. Eddy Baller is a Dating Coach based in Vancouver, British Columbia, Canada. Coaching since 2011, Eddy specializes in confidence building, advanced social skills and relationships. He runs his own dating consulting and coaching service named Conquer and Win, the only BBB accredited dating coaching business in Vancouver. Conquer and Win helps men worldwide have the love lives they deserve. His work has been featured in The Art of Manliness, LifeHack, and POF among others.

If there’s someone you can’t stop thinking about or you get butterflies when they walk by, you probably have a crush. Approaching your crush is nerve wracking enough, but it can be even harder when you and your crush are a little shy. Thankfully, there are a few ways you can break the ice and have a fun conversation with the person you like without feeling awkward.

How to start a conversation with your crush without it being awkward

Eddy Baller
Dating Coach Expert Interview. 7 February 2020.

  • If your crush likes art, you could talk about your artistic skills and which mediums you’ve been using.
  • If you know your crush is into music, ask them if they’ve seen any live bands lately.

We all have crushes, don’t we? Whether you are in your 20s or still in your teens, there is bound to be a crush now and then who is too cute to not even try to approach. But how do you talk to him without it being super duper awkward? So, being the good women that we are, here are 10 easy ways to talk to your crush!

1. Know thy audience

Before you actually go and talk to him, try to pick up a few things about him. You can subtle stalk him on Facebook or Insta, just to get a rough idea about what exactly to talk to him about and the things that he is interested in.

2. Ask for his opinion

If you follow step 1, then it’s gonna help you figure out what he likes and dislikes. So, you can start a casual conversation by talking about something he likes (he doesn’t have to know that you know) and asking his opinion on it. Obviously he will be excited about it and who knows, you might find something you both love. *Wink*

3. Questions to the rescue!

This one’s a gem of an idea, especially for people who are not big talkers! By asking him questions, he will do most of the talking and you will get to know him better in the process. Also, asking questions will lead to more open-ended conversations, instead of the awkward ‘ummms’ and ‘ohhs’ and ‘yes and ‘no’ answers!

4. Sit close by…

If you are in the same class or have gone out with friends, try to sit next to him or somewhere close by. It’s natural for any person to talk to people around him/her, so, you most likely will be able to start a conversation with him one way or the other.

5. Invite him for a casual outing with friends

If you have some mutual friends, make a plan with them and ask him to come along. The two of you going alone for the first time may feel awkward, but this definitely won’t. You guys can go out for lunch, bowling or maybe a movie?

6. Social media cheat code!

Social media has made things so much easier. So, go ahead and use it to talk to him. Start a casual conversation with him on Facebook and follow it up with some more chit-chat the next day. It will simplify things and there will be no awkwardness either!

7. Offer and lend

Offer to help him out with a problem he might be having. Or if he is looking to borrow a book or anything else that you have, lend it to him. It usually makes for a good conversation starter.

8. Ask him for help, even if you don’t particularly need it

If he lives somewhere around your place or if you go to the same class or share a workplace, ask him for help. It could be as simple as asking for directions or helping you understand something work related. It’s a very effective idea!

9. Compliments work like magic

And even better if you give him a not-so-obvious compliment. For instance, ‘Hey, I love that book you are carrying. It is so interesting’ would work way better than a simple ‘You look nice today’. It will get you talking about something you both are interested in, and needless to say, it will be a more interesting conversation!

10. Put truth and dare to good use

If you run out of all kinds of options, use the truth and dare excuse. Go up to him and ask him out for coffee saying that it was a dare from your friends. If he says yes, then yay! If he doesn’t say anything or just laughs off the whole thing, you can use that opportunity to have a genuine conversation with him. Once the ice is broken, you won’t feel awkward talking to him anymore.

It is normal to have a crush. Every one of us has experienced that. However, what is hard about having a crush is when you don’t know how to start a conversation. Of course, talking to your crush is different from talking to someone that you don’t have feelings for.

You will feel awkward and shy. Sometimes, you start to stutter because you’re the whole body is shaking when you try to talk. However, you need to save a lot of confidence in you so that you’ll come out with meaningful conversations that your crush must remember after.

Don’t think about it too much! You can get away from shame and awkwardness if you learn the six tips we’ve compiled below! Save yourself from that sweaty feeling when talking to your crush, and you will surely get the excellent result that you always wanted by following the questions you can start to ask your crush today. Check them out below!

1. Ask about your common interests.

It is a big advantage if you and crush share the same interests, whether it has something to do with school or your hobbies. Of course, it will be easy for you to open up about a topic that you know a lot of information. For example, if he loves to play video games, you can ask for an update about his level on the game and his favorite heroes to use. This will make the conversation more engaging because you are asking him a question about something that he loves to do best. Surely, he will ask you if you are also into it, so it’s your time to utilize that to keep the conversation going.

You don’t have to tell him that you are also into the same hobby because he might think that you’re bragging about it. Make sure to wait for him to ask questions before you overshare. If you’re not that closes, please don’t make it too obvious that you know everything about his whereabouts. It will be weird for him if he feels like you’re a stalker who is just trying to be friends with him. Ask to follow up questions but not too many. Let him answer the first one the proceed to the next. It will also help if you introduce yourself as someone who has attended the activities that he has attended. Use those activities as proof that you are interested in his hobby too.

2. Ask a favor.

Asking a favor is also one of the effective tips to start a conversation with your crush. Make sure that you’re kind enough to greet him, so you should also learn the different ways to say good morning and pick one that you think suits best as a greeting. Your crush must be kind enough to do your favor. Just don’t ask a favor that is too hard for him to do if you don’t want him to drop the whole conversation. For example, you can ask him simple questions like, “Have you seen Mrs. Reyes?” or “Can I borrow your Math book?”. If he asks you what it is for, the better. Again, always remember that favor must be something that he can do easily for you.

3. Compliment him.

Well, complimenting someone is easy, and it starts a good conversation. Compliments can flatter the person you are talking too, which makes the conversation engaging. And because you’re doing it to your crush, it might be hard for you to compliment him without him thinking that you are flirting with him. You don’t have to be afraid. You have to be sincere. For example, if he does something exceptional, send your congratulations with cute words for him that will make him more flattered. If he responds to your compliment, you might want to add another statement or question that relates to the topic that you’re complimenting to him.

4. Ask his opinion about a certain topic.

There are a lot of happenings around, and you can use any of it to start a conversation with your crush. For example, if there’s news about the banning of cellphones in the classroom, you can ask him about his opinion about it. In that way, he will have to explain his side and might ask you about your opinion too. So, make sure to back up yourself with the following questions that are related to the topic.

Furthermore, in order for your conversation to not be boring, make it more fun and engaging. It doesn’t have to be as controversial as politics and religion, as long as he can talk about his stand, the conversation will get going. Although the topic is simple, he might mention something that you can ask about, which leads you to a new topic that you both can talk about.

5. Ask more related questions to keep the conversation going.

Talking to your crush is like studying a school report. You must know the topic very well so that you can ask related questions to keep the conversation going. For example, if you like to tell him that you love to draw, you can still ask him first about his favorite anime character. It is a bonus if you have already sketch that anime character so that you can show it to him right away. In this way, he will stay interested in what you’re talking about because you also have a sketch with you.

Once the conversation has started, it will be easy for you to share other things that you love doing. You have to start it with questions that will lead to the topic that you want to introduce to him. You don’t have to directly tell him that you’re into drawing most, especially if he’s not asking about it. Learn the beauty of gradually introducing the topic with a series of questions.

6. Start by making funny jokes.

Everybody wants to have a good laugh. So if you have a sense of humor hiding within you, it’s time to unleash that. Start the conversation with your crush with a joke. Make it creative enough that even a smart person can laugh about it. It is good to joke around things when the whole squad is serious. It will recreate the mood around and even the mood of your crush.

Use it as an ice breaker. Observe the whole situation and use the things you noticed around you. Bear in mind to not joke around things that might offend him and the people around. For example, if you get a very low score in your exam, you can start a joke by kiddingly ask about an available home to stay after your exam. Surely, that will create a good laugh on his side, and you can ask about his score too. If he says he got a low score too then, you can tell him to go with you and find a new home. Or if he got a high score, you can kid around asking him to tutor you.


Make sure to bear in mind the tips we have mentioned above for you to have a good conversation with your crush that will not end with just a yes-no answer. Remember that these are just the starter packs for you to talk to your crush. If you improvise and talk about endless things, you won’t have any problem at all.

How to start a conversation with your crush without it being awkward

Whether you’re his acquaintance or a total stranger, there are dozens of ways to approach your crush. Some are bold, while others only require a small amount of bravery. Whatever method you choose to use, you’re sure to get his attention. Decide which of the following ways to approach your crush would be best for you, and then put it to the test. You have to try in order to succeed.

Table of contents:

1 Question after Question

If you work with him or have a class together, ask him for his opinion on an upcoming project. If you always see him while riding the train, ask him directions to a certain location. Unless he’s antisocial, any question from you will receive an answer. In order to keep the conversation going, have additional questions to ask after the first is answered. One of the best ways to approach your crush is by posing a question, because it won’t be hard for him to respond. Just don’t question him so much that he thinks he’s on a quiz show.

2 Honesty’s the Only Policy

“Hey, you’re in my chem class, right? I’m not sure how we haven’t spoken yet. I’m Elizabeth.” It’s as simple as that. Of course, you should substitute the generic ‘chem class’ with wherever you actually know him from and ‘Elizabeth’ with your actual name. It’s nothing fancy, but it’ll get the job done.

3 I Spy

If you see your crush reading a certain book, wearing a band shirt, or listening to music, start up a conversation about it. He’s obviously a fan of it, so he should be happy to have a chance to talk about it. If you’ve never heard of the author he’s reading or the band he’s listening to, don’t pretend that they’re your favorite. A lie will be easily found out. It’s better to say that you’ve been looking for new books to read, and ask him if he recommends the one in his hands.

4 Help, I Need Somebody

If he lives in the apartment across from yours, you can be bold and ask him for help with your car. If he’s studying from the same textbook as you, ask him if he can explain a certain concept to you. The task doesn’t have to be complex. It could be something as simple as asking if he’ll hold your coffee for you while you tie your shoe. Whatever works.

5 Consumer Compliments

You don’t have to compliment a physical feature, like his beautiful blue eyes or muscled arms. It’ll feel more natural to comment on something that he’s carrying with him. If your crush is on his phone, compliment him on the case. It can lead to a conversation about new upgrades and your favorite apps. When it comes to technology, there are so many things to discuss that you’ll be talking to him all night.

6 Collide with the Guy

If you’re leaving the same building, try to time it so that you hold the door open for him. After a brief exchange of ‘thank you’ and ‘you’re welcome,’ you can continue the conversation. If you’re on a bus together, you can choose the seat next to him. Since you’re already nearby, it won’t be weird for you to begin talking. In fact, it would be even more weird if you sat there quietly.

7 Common Complaints

It’s not good to be pessimistic, but it helps to vent a little. Bonding over something that you both hate can be simpler than finding something that you both love. If you’re in the same line at the supermarket, you can complain about the long wait or the prices. Just be careful, because you run the risk of having him disagree with you. If he’s optimistic and upbeat, this could backfire.

Be brave and go talk to that special boy! Are you on speaking terms with your crush? Do you think your relationship is going to go anywhere?

You finally did it—you got to the texting stage with your crush.

Only, things didn ‘ t quite go as planned. You were going strong for a little while, but over time the conversation slowly fizzled out. How do you start things up again without making it awkward for everyone involved?

We may have the answer. Keep scrolling for our tips on how to rekindle a conversation with your crush.

Reference a Joke

Rekindling a conversation with your crush doesn ‘ t take a linear path. Since you ‘ ve already established a connection, you can use numerous methods to relight the texting fire. One tried and true technique simply requires that you reference a joke from your past conversation. Whether it was something you used to tease each other for, an inside joke you developed or a hilarious meme you both loved, a witty text communicates your interest in chatting with them again in a laid-back, casual way. It ‘ s the perfect opening to restart the convo on a positive note, instead of making things uncomfortable for the both of you.

How to start a conversation with your crush without it being awkward

(via Unsplash)

Acknowledge the Weirdness

If you can ‘ t think of a joke that would elicit a reply from your crush, there ‘ s no shame in acknowledging the weirdness. You guys used to talk all the time and now it ‘ s radio silent? C ‘ mon, it is a little odd. Of course, you can ‘ t be overbearing or passive aggressive with your text. A simple ” Hey, stranger! ” or ” We haven ‘ t caught up in a while, what ‘ s up? ” gets the point across beautifully. By acknowledging your lapse in communication in a non-threatening way, you eliminate the need for either of you to feel bad about it. If you end up dating down the line, then you can ask them why they disappeared on you for two weeks straight. It happened, but for now you can move on and talk about other things.

Skip the Small Talk

If things fizzled out once before, the chances of them fizzling out again are even higher. If you ‘ re tired of the endless back and forth, skip the small talk and get straight to the point—text your crush and ask them on a date. It can be as casual as asking if they want to hang out this weekend or as bold as telling them that you like them and want to pursue a relationship. It ‘ s a daring move, but it will definitely push you out of the gray area and eliminate the need for another month of texting that doesn ‘ t really get you anywhere.

How to start a conversation with your crush without it being awkward

(Easy A via Screen Gems)

Start a New Convo

Probably the easiest way to rekindle a text conversation is to simply start an entirely new convo. While it can feel painfully personal when someone doesn ‘ t reply to your text message, it ‘ s not always as meaningful as it seems. Text conversations can go through ebbs and flows—a lack of response doesn ‘ t have to be the end of the world. If you ‘ re still trying to feel things out, send your crush a new text. If they ‘ re interested, they ‘ ll reply. If not, we promise no one will judge you for sending a ” how was your day? ” text.

Go in With the Compliment

Even the best among us love a little flattery. If you can boost your crush ‘ s ego a little, you might up your chances of restarting a genuine convo. Send them a simple, but sincere compliment to reignite their interest. Anything from complimenting their outfit that day to letting them know you ‘ re still thinking of them can be a sweet way to ease back into a conversation.

How to start a conversation with your crush without it being awkward

(Grown-ish via Freeform)

Know When to Give Up

Unfortunately, there is a harsh, but true reality that has to be faced. If your conversation with your crush keeps dwindling out, they ‘ re just not that into you. For your own sake, and theirs, you need to know when to give up. We recommend limiting yourself to one restart text per crush. If they don ‘ t respond, consider them uninterested in a relationship with you. You ‘ ve made your interest apparent—the ball ‘ s in their court now. By knowing when to give up, you can save your crush from a lot of awkward avoidance, as well as yourself from plenty of potential embarrassment.

How to start a conversation with your crush without being awkward? Is it really Possible? Then How can I Do this? You might have these kind of questions in your mind. And you want someone to answer these questions perfectly. Okay, I can do this for you. In this Article, I’m going to tell you 3 ways to start a conversation with your crush which will lead to more hanging out.

1- Voice Internal Questions

While we walk, talk or eat, go somewhere or doing anything, a lot of questions pop up in our mind. And we ignore them unconsciously and sometimes intentionally. And do not give voice to those questions. And sometimes search for their answers on google.

But if you ask those questions to the people you want to talk, then it will be a very effective way to start a conversation. So next time, whenever you like to know about something, ask it to your loved one. Not only it’ll provide you an opportunity to talk with them but also will make them feel important. And when you make someone feel important, they like you back subconsciously.

2- Make Statements

Conversation means two sided interaction . Where two people share their ideas. Asking more questions can make your conversation one-sided and boring. So it’s very necessary to make more statements and asking fewer questions. If you see them reading a book, just say “I love to read self improvement books, what kind of books you like? ” Share your thoughts and ideas and urge them to do so. Make them feel that they are making a choice to continue the conversation with you. So if you want to know how to start a conversation with your crush, then this is the best way to do it. GO AHEAD.

3- Introduce Yourself

Introducing yourself to the person you like is the simplest way to start a conversation with them. Just Go to them and say Hi, My name is __. And ask them about your surroundings. E.g The weather seems very bad today. Do not you think it will rain? So what do you do? And Keep the c onversation going. But make sure that when you approach them they are free and available. Don’t bother people who are busy in their work.

A lot of people feel awkward when a stranger pops up and start asking them boring questions. So before starting a conversation with someone just make sure that the person knows you. They have seen you twice or thrice in their town and street. First, make them familiar with you and then start a conversation.

So these were the 3 ways, How to start a conversation with your crush. I hope you’ll Like it and will Subscribe for more articles.

I don’t know who needs to hear this, but if you’re trying to get a convo going with your crush, you can do better than texting them “hey рџ™‚.” The best conversation starters are ones that inspire curiosity, invite a response, and open the door to other topics — and I’m sorry to say that “hey” does none of those things. If you’re in need of texts that start a conversation with your crush when you’re bored and looking to chat, then I’ve got some suggestions that are sure to pique their interest.

The best way to get a playful conversation going is to keep things light. (For example, it’s probably best not to open the conversation with “What is your greatest fear? Mine is dying alone.”) Questions are the best way to instigate a convo (because, you know, they require a response). You can ask your crush for their opinions, reviews, preferences, and recommendations on any number of topics, and sometimes, the most random questions lead to the most interesting conversations. Here are just a few questions you can use to get the ball rolling (and help you learn a little bit more about your crush in the process).

1. “Have you been watching Love Is Blind? If so, plz share your thoughts, because I honestly don’t know what to think.”

2. “I’m pretty sure I’m the only person in the city who didn’t realize it was going to rain today and didn’t come prepared with an umbrella. Is your day going better than mine?”

3. “I’m trying to pick a movie to watch and I’m curious: Is Parasite as good as everyone says?”

4. “I’m taking a poll on which is better: Disney World or Disneyland? And yes, there is a right answer.”

5. “Will you go to this rescue puppy website and help me pick out a dog? I’m not actually getting one, but I like to pretend I am.”

6. “I’m trying to plan my next vacation. What does your ideal trip involve: camping, hiking, sightseeing, lounging, or all-you-can-eating?”

7. “I took a Barry’s Bootcamp class yesterday and I’m sore in places that I didn’t even know existed. Have you ever been to Barry’s before?”

8. “Have you ever gotten a Shamrock Shake? I want to try one but I’m skeptical.”

9. “I’m about to start watching Game of Thrones. Is there anything I should know before I begin this journey?”

10. “Serious question: Do you think I could pull off a leather jacket?”

11. “There’s a spider in my apartment. Will you come over and get rid of it, or do you also have an irrational fear of bugs?”

12. “I’m ordering a pizza and I don’t know what to get. Will you pick three toppings with me?”

13. “Will you send me the best meme you’ve seen today? I need a good laugh.”

14. “I’m rewatching The Office, and I want to know what you think: Are Jim and Pam relationship goals or totally overrated?”

15. “What do you think is worse: people who celebrate their half-birthday, or people who celebrate their birthday week?”

16. “Have you ever purchased anything from an Instagram ad? I bought three different things from ads this past week and I’m concerned for myself.”

17. “What do you think is the most annoying thing a person can post on their Insta Story?”

18. “What’s your most toxic trait? Mine is waiting a week before I reply to people’s emails.”

19. “If you could be trapped in an elevator with any celebrity for 12 hours, who would it be and why?”

20. “What’s your opinion on flip flops? Unsightly or essential?”

21. “I accidentally called my professor ‘mom’ in class this morning. What’s the worst thing that’s happened to you today?”

The best part: If your crush doesn’t have an opinion on something, you then have an excuse to experience it together on your first date. Just saying!

Communication is the best way to form a bond. Through communication, you get to know them more and be close to them. But how do you actually start that journey?

In order to communicate with someone, all you need to do is a quick start. It might seems daunting and confusing because it needs to be perfect. If you are confused, all you need to do is to know how to start a conversation with your crush for the first time;

1. Know Their Interest

First, you need to know what their like because usually people can talk on and on about what they really like.

2. Know Their General Details

Whether it’s about where they live, what they do, or who they are related to, all of this can help you make a conversation.

3. Befriend Their Friends

How to start a conversation with your crush without it being awkward

Being friends with their friends is a great way to be close to them. This is because their friends might introduce you to him.

4. Be Close To Their Family

If their family already likes you, it is more likely that you will have a strong bond with your crush too.

5. Pretend To Bump Into Them

Bumping into them is a funny and great experience to open up a conversation. A simple sorry can be followed by any conversation opener.

6. Compliment Them

Complimenting them makes them blush and makes them feel like you are really kind.

7. Follow Them On Social Media

Doing this means that you can direct message them, comment on their post or like their post.

8. Ask Them About The Date, The Weather, Or Other Small Talks

Small talks can lead up to big talks and it is a way to break the ice and awkwardness before the conversation.

9. Show That You Love What They Love Too

How to start a conversation with your crush without it being awkward

Showing interest in what they love actually makes them feel closer to you which makes them want to strike a conversation with you.

10. ‘Accidentally’ Text Them

This accidental text is a great ice breaker to make other conversations in the future. This can even lead them to show the Signs Your Crush Likes You Through Texting.

11. Help Them Out With Something

Helping them out shows that you are kind and can make them show the Signs She is Into Me.

12. Say That You Need Their Help

People like to feel needed and it actually makes you bond closer with them. This is the easiest how to start a conversation with your crush for the first time.

13. Treat Them To Something

Treat them to a drink or to a food to make them want to chat with you because of your kindness.

14. Gently Show What They Did Wrong

Point out their flaw gently on the small stuff like a celery on their teeth, an untied shoe, or something else.

15. Pretend That Talking To You Was A Dare

When you make it seem like you are dared it actually makes them more eager to help you out.

16. Be The Asker Of Questions

When you ask questions, the conversation will flow easily and you will feel more rewarded.

17. Dress Better

How to start a conversation with your crush without it being awkward

Dressing better actually make you have their attention and increase the chance of you talking to them.

18. Casually Make Eye Contact With Them

Eye contacts that is kind of flirty is a Physical Signs A Woman Likes You Like Crazy that makes conversations made easily.

19. Walk Past Them

This simple act makes you be in their mind for a split second.

20. ‘Accidentally’ Call Them

Just say that you press the wrong number and then you can continue the conversation with them.

Tips To Make A Great First Conversation With Your Crush

If you are not the typical social and fluent person that can pull out a great conversation starter anytime, then you need to know these tips to make a great first conversation with your crush;

1. If Things Are Getting Boring, Change The Topic

To keep the conversation going, change the topic often.

2. Talk About Yourself A Little

This is a great topic that might make them show Signs a Woman is Interested in Me.

3. Share Your Opinion About Something

How to start a conversation with your crush without it being awkward

A debatable opinion about something can make the conversation flow easily.

4. Talk About Work

Alhtough it sounds boring, work is a general topic that could be the booster to a conversation.

5. Ask For Their Opinion On Something

When people are asked about their opinion,they speak fluently and in long interals about it.

6. Be Calm And Casual

Seeming awkward won’t make the conversation better.

7. Suppress Your Nervousness

Nervousness is a thing that kills the vibe.

8. Show That You Are Happy To Talk To Him

Excitement from you can be reciprocrated by the person you are talking with.

9. Talk Slowly With The Right Tone

This shows that you are calm.

10. Be Confident

11. Don’t Force It

Forcing it stops them from talking to you again.

Signs That They Start To Like You

How to start a conversation with your crush without it being awkward

When you have enough conversation with someone, you will see that the connection is starting to appear. You will find it too if you see these signs that they start to like you;

1. Showing The Interested Body Language

Leaning in, a smile, and a touch of arm is a few body language you should look out for.

2. Not Wanting The Conversation To End

They change the topic or say that they really enjoy talking to you to keep the conversation going.

3. Not Being Afraid To Open Up

Once they get comfortable, they even open up to you.

You need to throw away that nervousness and doubt that goes into talking to him and use the simple ways on how to start a conversation with your crush for the first time. If you do, you will see that the both of you are starting to bond at a great speed and who knows what great things will happen after that?