How to Start a Conversation with Your Crush (With Examples!)

If you’re done watching your crush from the shadows, then you must be wondering how to start a conversation with your crush.

A simple “hello” might do the trick. But, what would you say next?

Since not everyone is a good conversationalist, going with the flow might not help you keep the conversation going.

However, you know for a fact this must be done and I agree with you. 

How else would you get to know your crush better? How else would you give them a chance to fall for you as well?

At this point, talking to them is essential. Who knows, maybe your crush already likes you and all you need to be is be confident and to break the ice.

Or, maybe they don’t even know you exist. So, you have to do something to be on their radar.

In this regard, effective communication is your best friend. It helps build healthy relationships right from the start.

There’s no need to try and deceive them or hide your purpose. You don’t have to appear as someone that you’re not. 

Introducing yourself and expressing your interest in them is a basic way to start a conversation.

However, I understand how scary that may be for you and that’s why I want to go through every step with you.

Let’s jump straight in!

Here’s How to Start a Conversation with Your Crush:

Below, I’ve shared 3 steps guide to start a great conversation with your romantic interest to get things moving in your dating life.

Part A: Before You Start a Conversation With Your Crush In Person

1. Make sure you’re prepared to approach them

Especially if you’re a shy person, you will need to have a solid plan in place before you approach your crush.

This will help boost your confidence.

You’ll feel ready to face every situation that might occur, including an awkward one, but more about that later.

On top of that, you won’t come out of this situation feeling as if your expectations were met or unmet.


Because the first thing to keep in mind is this: You shouldn’t have any preconceived ideas about how your crush will respond to your approach and how the first conversation should go.

Don’t spend time imagining a situation that’s probably going to be a lot different in real life. That’s not going to be helpful because you’ll compare reality with an ideal situation created by your mind. 

And that’s not fair. So, try to expect nothing and just be yourself. Also, take the following steps into consideration.

2. Pick a time and a place when you’re both free

Starting a good conversation with your crush IRL involves a little planning.

You can’t talk to your crush when they’re with their friends or when they’re literally running to catch a train. 

In this regard, the time and place you choose to approach them matter a lot. It may increase your chances to have a pleasant first conversation with them, or not so much…

For example, if your crush is a schoolmate or coworker, maybe you see them often in the hallways or in the lunch/break room. Most often than not, these are crowded and noisy places.

They don’t encourage communication. On the contrary, they hinder it and that’s far from what you want.

But if you meet at an afterschool get-together or a random social event, then the time and the place could be right.

They should be in a good mood and open to socializing considering the environment they are in.

So, if you’re aware of an upcoming event or something similar, don’t hesitate to go and look for opportunities to talk to them.

Or, if you see your crush one day sitting alone, reading something, take that chance and start a conversation with them. You can be spontaneous, too!

Seizing the moment is another one of your options. However, the perfect moment might never come, so I encourage you to take action sooner rather than later.

3. Try to find out more information about them

Here’s another pro tip: The more you know about them, the better.

I know this sounds a little bit like stalking, but it isn’t.

Trust me.

You need to know more about your crush’s interests, hobbies, and favorite activities because that’s how you’ll find your conversation starters. 

Also, you may find out about shared interests, a fact which should increase your chances to have a great first talk with them.

In this regard, you can use social media. Search your love interest’s profiles on various SM platforms and gather the info you need.

You want to learn more about what they like.

What else?

If you have the chance to observe how they behave with others and around you, by all means, do it!

Watch how friendly/reserved they are with others. Also, see if they react in any way when you’re around. 

For example, if they smile when they see you, you have the green light to talk to them. Their smile is pretty much an invitation to talk.

Other positive body language signs are when your love interest makes eye contact with you.

If you discover that they’re generally reserved, don’t expect them to act differently with you. You might have to make more effort to get their attention.

Part 2: Starting & Having The First Conversation

4. Pick & Use The Right Conversation Starters

Are you prepared to start talking to your crush?

If you’ve learned more things about them and analyzed their behavior lately, you should be ready to go.

You can break the ice by asking them open-ended questions, giving them compliments, making observations, and sharing experiences.

Pro tip: Research shows that pets play a role in human courtship and dating. To be more precise, if you have a pet, you can use it as an opening line. 

You can show them a picture of your pet and let things flow from there. In case they also have a pet, they’ll definitely share details about that and their experience with them.

Below, I’ve shared a few way to start the small talk with your crush.

5. Ask Your Crush Open-Ended Questions

Do people still read? What is that book about?

I noticed you’re wearing a T-shirt with a dog. What do you think about owning a pet?

I saw you sitting alone. What were you daydreaming about?

I keep seeing you here. What do you like about this place?

I was wondering something… How do you know when you like someone?

Here’s the list of questions to ask your crush.

6. Give Your Crush Compliments Based on Genuine Observation

I just wanted to say how much I love your style. You don’t look like the other guys/girls.

Congrats on your presentation. I learned a lot from it and I have a couple of questions.

No way! You have an X T-shirt. I love this band so much. What’s your favorite song?

Your attitude in front of the teacher/boss really caught my attention. You are a bold person.

I noticed your dance moves. You are a talented dancer.

Here’s the complete list of…

7. Ask Your Crush About Their Person Experiences or Events:

I saw you at the get-together last night. How was it for you?

Do I know you from the last teambuilding activity?

I saw you checking out the art class. I don’t recommend taking it. 

How is life treating you? Are you having fun?

I can’t believe what X did! Did you see that?

Part C: Keeping The Conversation Flowing

8. Get involved in your conversation with them

Immediately after you start a conversation with the person you have a crush on, you should get involved one hundred percent to get past the initial small talk phase. 

Regardless of how shy you are, you have to make an effort and maintain eye contact with them when they reply to you.

Eye contact conveys your interest in what they’re telling you. 

At the same time, it’s recommended to keep the conversation light by cracking a few jokes or making some witty remarks.

Remember: you don’t have to try really hard. 

Just act like yourself without getting too serious. However, also keep in mind to listen actively and avoid being chatterbox.

This means that you should really listen to what your crush says and ask them follow-up questions. Also, it means that you should be mindful of their answers and adjust yours based on them.

You see, most people think about what they’ll say next when another person is talking. They don’t listen without judging or formulating something to say in return. 

This makes communication a lot harder because we don’t really listen. So, don’t be that kind of person. Listen as if you care and things will take a turn for the better.

If this conversation is happening online then I would recommend you to go through these two articles:

9. Handle awkward situations with humor

Look, regardless of how prepared you are to start a conversation with your crush, you can’t predict everything. 

The truth is that there will be moments of awkwardness or uncomfortable silence during your first and next talks with them. 

So, it’s important to know how to handle them. The best way? Respond with humor!

Say something silly or make a joke if you feel things are not progressing in any direction. Acknowledging awkward moments alone is a reason to laugh.

Or, you could simply touch on a different topic and move past that moment of uncomfortable silence. This is where you can use the info you know about them or ask open-ended questions.

If nothing comes to mind, just look around you. There must be something you can make a remark about.

Try your best not to freeze if something like that happens. You and your love interest don’t know each other. So, it’s only natural for awkwardness to sometimes occur.

This doesn’t mean that you should end the conversation and flee. It would be best to move past that moment and leave your crush with a good impression. 

A popular technique is to say: “Let’s start over! I’m X, nice to meet you!


There is more than one way to start a conversation with your crush. If they don’t know you at all, you’ll have to introduce yourself and break the ice with a casual remark. 

However, if you’re already on their radar it should be simple enough to approach them directly when the time and place are right. 

After you start talking, keeping the conversation going could be ever trickier. However, if you do your research well, you’ll be prepared for that, too. 

One more thing you should be ready for is to feel awkward. Awkward moments are almost inevitable but you can use them to your advantage and make humorous comments about them. 

As long as you’re aware of all these aspects, you should succeed at having pleasant interactions with them.

You can also implement the openers I shared earlier on a dating app.

There’s also the possibility that they don’t respond positively to you. If that happens, follow Helepoli’s advice: just move on with your life.

Daniela Duca Damian
About Daniela Duca Damian

A journalist by profession, Daniela has been sharing her knowledge and personal experience in the psychology of love and relationships for the past 5 years. Her work is based on facts, practical advice and is meant to help everyone achieve their romantic goals. When she isn’t writing, she challenges her friends with meaningful questions about life.

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