How to Start a Conversation With Your Crush for the First Time (21 Tips + Expert Insights)

Let’s be honest, starting a conversation with your crush can be intimidating. You might worry about saying something embarrassing, running out of things to talk about, or getting rejected. These fears are totally normal, and we’ve all felt them too.

But you can’t let your fears stop you from taking a chance. Every great relationship starts with a simple conversation. And who knows? Your crush might be just as nervous and excited to talk to you as you are to talk to them.

If you’re ready to face your fears and take that first step, this article is for you. I’ll share practical and easy-to-use strategies for starting a conversation with your crush.

Introduce Yourself Confidently

Meeting your crush for the first time can be nerve-wracking, but a confident introduction shows that you’re comfortable in your own skin. Confidence isn’t about being boastful or over-the-top but it’s showing that you’re happy to meet them.

Here are some tips for a confident introduction:

  • Make eye contact and smile.
  • Speak clearly and avoid mumbling.
  • Stand tall and maintain a good posture.
  • Keep your introduction simple and direct.

Confidence comes from within, and even if you’re shaking on the inside. Believe in yourself. Everyone appreciates someone who is genuine and self-assured, not someone who is trying too hard to impress.

"When you see your crush, give yourself no more than five seconds to walk up to them and to say something… A good mind-trick is to count backward from 5, and when you get to 1 just take action without thinking…

The point here isn’t so much to have the perfect conversation or to know exactly what to say. It’s to get comfortable with approaching your crush."

— Steffo Shambo | Relationship Expert | Founder, Tantric Academy

Offer a Genuine Smile

Never underestimate the power of a genuine smile! It’s one of the simplest yet most effective ways to put your crush at ease and show that you’re friendly and approachable.

When you see your crush, make eye contact and offer a warm smile. I’m not talking about a forced or overly enthusiastic grin, but a sincere smile that reaches your eyes and radiates kindness and openness.

A genuine smile can help break the ice and make your crush feel more comfortable. Plus, smiling has been shown to boost your own mood and confidence, so it’s a win-win!

"A smile goes a long way when trying to talk to anyone for the first time. It immediately makes you seem more approachable while putting the other person at ease. 

If you smile and make eye contact, there is a good chance your crush may start the conversation before you even get the chance to."

— Alexis Wolfe | Dating Guru & Founder, NYC Date Nite

Make Them Comfortable

Making your crush feel comfortable is important for having a successful first conversation. When they’re at ease, they’re more likely to open up and engage with you. So, how can you create a comfortable atmosphere? Here are a few tips:

  • Choose a relaxed setting: If possible, start the conversation in a place where you both feel at ease, like a quiet corner of a coffee shop or a bench in a park.
  • Use open body language: Keep your arms uncrossed, maintain eye contact, and lean in slightly to show interest and receptiveness.
  • Listen actively: Show that you’re engaged in the conversation by nodding, smiling, and responding appropriately to what they say.
  • Avoid controversial topics: Steer clear of heavy subjects that could make your crush uncomfortable. Stick to lighter, more neutral topics at first.

Your goal here is to create a warm and inviting space where your crush feels safe and heard. By prioritizing their comfort, you encourage a meaningful connection and an enjoyable first conversation.

Find Common Interests

One of the best ways to start a conversation with your crush is by finding common interests. When you share something in common, it creates an instant connection and gives you plenty to talk about.

To find out shared interests, pay attention to your crush’s social media profiles, the clothes they wear, or the books they carry. You can also ask their friends or listen for clues in group conversations.

You can exchange opinions, share recommendations, and even plan future activities together. Knowing that you have something in common can make both of you feel more at ease. It’s always exciting to find someone who enjoys the same things as you do.

"The best way to connect with someone is to find common interests. You'll have endless things to talk about if you both talk about the things you're passionate about. 

Find a common ground between you and your crush, even if it's something trivial like your favorite ice cream flavor. It's a good starting point."

— Robin Sutherns | Relationship Expert | Editor, Galtelligence

Bring Up a Shared Experience

Shared experiences can be anything from attending the same class or event to growing up in the same hometown. When you bring up a shared experience, it creates a sense of familiarity and belonging.

  • Talk about a popular event or happening everyone’s buzzing about.
  • Maybe you sat through the same weird assembly at school? Or worked on the same project?
  • Even something as simple as the weather can tie you together (‘Crazy rain today, right?’).

Referencing a shared experience shows that you remember them and you share similar interests or habits. This familiarity can make the conversation flow more easily, reducing the awkwardness usually associated with talking to someone new.

Ask Open-Ended Questions

Unlike yes-or-no questions, open-ended questions encourage more meaningful responses. They give your crush the opportunity to share their thoughts, feelings, and experiences, showing who they are as a person.

When asking open-ended questions, avoid interrogating your crush or prying too deeply into personal matters. Instead, keep the questions light, fun, and relevant to the topic at hand. For example:

  • Ask things like “What’s your take on…” or “How do you feel about…”
  • Avoid closed questions that start with “Did you…” or “Do you have…”
  • Encourage stories or opinions to get the conversation going.

As your crush responds, listen actively and ask follow-up questions to keep the conversation going. Share your own thoughts and experiences when appropriate, but make sure to keep the focus on your crush and their interests.

"Use "how" and "why" questions. Doing this will encourage your crush to open up to you. Avoid questions that can be answered with yes or no, it would be difficult to keep the conversation going if you do that. 

It would also feel awkward if your crush was left with nothing to say to you because of the rough flow of conversation."

— Chris Pleines | Dating Expert, Dating Scout

Be an Active Listener

Active listening shows that you’re genuinely interested in what they have to say and value their thoughts and opinions. Being an active listener means giving your full attention to your crush, without getting distracted by your own thoughts or surroundings.

To practice active listening, focus on maintaining eye contact and using non-verbal cues like nodding and smiling to show that you’re engaged in the conversation. When your crush is speaking, resist the urge to interrupt or jump in with your own stories.

Instead, allow them to finish their thoughts and then respond thoughtfully, building upon what they’ve shared. Your crush will notice your interest in their words, which can make them feel special and respected.

Stay Positive and Upbeat

Talk about things you are passionate about and ask them what excites them too. Avoid dwelling on negative or controversial topics, especially in a first conversation where you’re both still figuring out comfort levels.

  • Share positive experiences or funny anecdotes.
  • Smile and laugh—not forcibly, but to convey a relaxed vibe.
  • Steer the conversation towards uplifting topics if it starts to veer into anything heavy.

I personally find that starting with a funny story or joke can help set a positive tone from the beginning. Your aim is to leave them with a good feeling after your conversation. People are naturally drawn to those who can uplift their spirits and make them laugh.

"You won’t be able to start a conversation with your crush without the right conversation starters. Sometimes you ask questions and the answers are just a yes or no. Never do that. Start with topics that you know will drive the conversations deeper and longer."

— Robin Sutherns | Relationship Expert | Editor, Galtelligence

Give a Sincere Compliment

When you give a compliment, do it naturally. Don’t force it or overdo it, as it might come off as insincere. A well-placed compliment can be a great conversation starter too.

Effective ways to give a sincere compliment:

  • Mention something you genuinely admire about them (like their laugh or style).
  • Be timely and context-appropriate (like praising a recent accomplishment).
  • Avoid overloading—one honest, well-placed compliment is worth more than a dozen that could overwhelm them or make them uncomfortable.
"The best way to start a conversation with your crush is to focus on something about that person. You find something about your crush and pay him or her a compliment. Everyone loves a genuine compliment."

— May Bugenhagen | Certified Professional Matchmaker | Owner, Matchmaker May

Use Humor to Break the Ice

Using humor shows that you don’t take yourself too seriously and are comfortable enough to laugh even in new situations. This can make your crush feel more at ease with you.

Just a gentle reminder, avoid jokes that might be offensive or too sarcastic, as these can create discomfort. Instead, a short story of an amusing personal experience or light-hearted observations about your surroundings can work.

"Act confident until you feel confident. If you have a funny sense of humor, use humor to start off a conversation. Make a joke about something in the present. 

Be careful with sarcasm though, because that might put you in a negative light and make a bad first impression."

— May Bugenhagen | Certified Professional Matchmaker | Owner, Matchmaker May

Maintain Good Eye Contact

When making eye contact, aim for a balanced approach. You don’t want to stare intensely at your crush, as this can come across as intimidating or creepy. Instead, maintain gentle, steady eye contact, glancing away occasionally to avoid appearing too intense.

A good rule of thumb is to make eye contact for about 50-60% of the conversation, particularly when your crush is speaking. Remember to:

  • Make sure your eye contact feels natural and relaxed.
  • Pair your eye contact with a warm smile and friendly facial expressions.
  • If you struggle with maintaining eye contact, practice with friends or family members.

Pay attention to your crush’s eye contact as well—if they’re consistently making strong eye contact with you, it’s a good sign that they’re interested in the conversation. But if they seem uncomfortable or are avoiding eye contact, it might be a cue to give them a bit more space.

Comment on Your Surroundings

Commenting on your surroundings is an easy and non-intrusive way to break the ice, especially if you’re in a shared space like a café, park, or event. Plus, it shows that you’re present and attentive to what’s going on around you.

Here are a few examples of how you might comment on your surroundings:

  • If there’s something funny or unusual, mention it with a light touch.
  • Use what’s happening around you to ask a relevant question (like, “This DJ’s great, what’s your kind of music?”).
  • Draw parallels to something interesting, “Doesn’t this cozy coffee smell remind you of waking up to a weekend morning?”

Make sure to keep your observations positive, friendly, and relevant to your shared situation. By commenting on your surroundings, you’re creating an instant connection with your crush and giving them an easy way to jump into the conversation.

Ask Their Opinion on Something

People generally like to share their opinions, especially on subjects they care about. This makes asking for their opinion a fantastic strategy to initiate a conversation with your crush. Start with something light and relevant to the setting.

To effectively ask for their opinion:

  • Be genuinely interested in their response rather than just about filling the silence.
  • Encourage elaboration with follow-up questions or by expressing interest in their reasoning.
  • Choose a topic that is relevant to your shared situation or that you know they’re interested in.

Share a Fun Story

Personal stories often reveal a lot about your character, sense of humor, and interests. They can make you more relatable while also providing a glimpse into your life and experiences.

Tips for sharing a fun story:

  • Choose a story that reflects a positive aspect of your personality or highlights your hobbies.
  • Keep it brief and relatable. A long story might lose their interest.
  • Incorporate humor to keep it light-hearted.

Once you’ve finished your story, ask your crush if they have any similar experiences to share. This will help keep the conversation flowing and give you a chance to bond over your shared stories.

"[...] it's important for you to prepare two or three go-to stories, things that you feel comfortable talking about with anyone and you can talk in-depth about without feeling nervous, afraid, or just messing up what you're talking about."

— Steffo Shambo | Relationship Expert | Founder, Tantric Academy

Reference Something They Like

One of the best ways to start a conversation with your crush is by referencing something you know they like. It could be a hobby, a favorite band, a TV show they enjoy, or even a place they love to visit.

Here are some ways to reference something they like:

  • Mention their favorite TV show, book, or band.
  • Encourage them to talk more about their passion.
  • Ask them for recommendations based on their interests.
  • Share your thoughts or experiences related to what they like.

When you bring up something they like, it makes them feel understood. It gives them a chance to talk about their passions. And who doesn’t love discussing their favorite hobbies or interests with someone who shares their enthusiasm?

"For your first conversation with your crush to not be awkward, start the conversation by talking about something that you know he or she is interested in. This will ease the flow of words both for you and your crush because there is a topic to talk about.

However, you have to make sure that you are knowledgeable about the topic—you wouldn't want to stutter or pretend you know a lot when the reality is that you don't."

— Chris Pleines | Dating Expert, Dating Scout

Keep the Conversation Going

Once you’ve started a conversation with your crush, it’s important to keep it going. You don’t want to let the discussion end abruptly. The key to keeping the conversation flowing is to show genuine interest, ask follow-up questions, and share your own thoughts and experiences.

If your initial topic starts to fade, have a couple of backup questions or topics ready. For example, if you started talking about a movie, you could transition by asking about other genres they like or if they have any movie recommendations.

But if you find yourself struggling to keep the conversation going, don’t be afraid to circle back to an earlier topic or ask your crush a new question. The most important thing is to stay relaxed and enjoy the process of getting to know each other better.

Respond to Their Social Media Story

Social media has become a great way to connect with your crush and start a conversation when approaching someone in person feels scary. One effective approach is to respond to their social media stories, particularly on platforms like Instagram or Facebook.

When responding to your crush’s story, keep a few things in mind:

  • Be genuine and specific in your comment or reaction.
  • Avoid generic responses like “cool” or “nice”—instead, mention something specific that really caught your attention.
  • Use the story as a springboard for further conversation by asking a related question or sharing your own similar experience

By replying with your crush’s story, you’re slipping into their circle, making it easier to start a conversation the next time you see them in person.

Send a Funny Meme or Video

Sending your crush a funny meme or video is a great way to start a conversation showing you have a sense of humor and can be a fun, easygoing person to talk to. Plus, if your crush finds the content amusing, it can create a positive association with interacting with you.

When choosing a meme or video to send, consider your crush’s interests and sense of humor. You want to select something they’re likely to appreciate and find funny, not something that might offend or confuse them.

Then, ask what they thought of it, share your own reaction, and see where the discussion takes you. Just remember to keep it casual and fun—the goal is to create an enjoyable, stress-free interaction that leaves your crush wanting more.

"Starting a conversation on a funny note sets the light-hearted tone that you’re looking for in that first-ever conversation. If you can find a funny meme that somehow relates to your crush, that would be ideal."

— Alexis Wolfe | Dating Guru & Founder, NYC Date Nite

Bring Up a Memory You Have of Them

Mentioning a shared memory can be a great way to start a conversation with your crush. It shows that you remember and find your previous interactions significant enough to recall. 

When choosing a memory to bring up, opt for something positive and lighthearted. It could be a funny moment from class, a shared experience at a school event, or even just a brief exchange that left you feeling happy and connected.

The key is to keep it casual and avoid anything too personal or intense, especially if you don’t know your crush very well yet.

Ask for Help With Something Small

Asking for assistance is a subtle sign of trust. It shows that you value their opinion and expertise, giving them a chance to feel helpful and needed. Plus, it creates an opportunity for further interaction and follow-up conversations.

When asking for help, choose something specific and manageable. You don’t want to overwhelm your crush or make them feel like you’re taking advantage of their kindness. Instead, opt for a small favor or piece of advice that aligns with their interests or skills.

  • Simple things work best—think about borrowing a pen, asking for directions, or needing advice on a simple matter.
  • Express genuine gratitude afterward—it’ll make your crush feel appreciated and significant.

This small exchange can easily transition into more topics of conversation, like what they’re good at or their experiences around the help you sought. It’s a great way to show your crush that you value their input and want to learn from them.

"If you want to strike up a conversation with your crush, ask them for help with something. Asking them for the WIFI password at a cafe, for example, is an easy way to start a conversation. 

If they’re also interested, they’ll jump on the opportunity to talk to you… Asking for a small favor, such as helping you with a work problem, gives you an excuse to talk to them."

— Cierra Loflin | Chief Marketing Officer, Zodiac Guides

Suggest a Casual Hangout

Suggesting a casual hangout is a bold yet effective way to start a conversation with your crush and take your connection to the next level. It shows that you enjoy their company and want to spend more time getting to know them outside of your usual interactions.

When suggesting a casual hangout, keep it low-key and pressure-free. You don’t want your crush to feel like you’re coming on too strong or expecting too much too soon. Instead, frame it as a friendly invitation to explore a shared interest or experience something new together.

Remember, the goal is to create an opportunity for further interaction and connection in a comfortable, easygoing setting.

More Insights from the Experts

“Remember not to let your nerves get the best of you. It takes a good amount of courage. Don’t be afraid to be rejected because it’s always part of the experience. What’s important is that you remember to have fun and be yourself always.”

— Robin Sutherns | Relationship Expert | Editor, Galtelligence

“When we talk about getting into the right mindset to do anything, at the end of the day, what it all comes down to is practice. Putting yourself through different experiences so you can learn how to handle them.

So when you actually go for what you want, you’re ready, but how exactly do you practice for talking to your crush?

If talking to them is the thing that you’re scared of, how do you practice talking to them? Instead of talking to your crush, what you’re gonna wanna focus your attention on is talking to girls or guys that you’re less intimidated by.”

— Steffo Shambo | Relationship Expert | Founder, Tantric Academy

“Well, first thing’s first: you need proximity. Hard to chat your crush up from across the room… The good news is a lot of times crushes are reciprocal, and your crush may just get close to you too! So sometimes this part handles itself. If not though, you’re going to need to find a reason to get close.”

— Chase Amante | Founder, Girls Chase

“The easiest way to start a first-time conversation with your crush is to be ‘at the moment.’ What this means is you don’t want to overthink a conversation and just use whatever is around you as a conversation starter…

Firstly, you want to be aware of the environment because your current location provides you with a conversational topic… Next, you want to be aware of what’s taking place around you because that will provide the content of the topic.”

— Maxwell Kamlongera | Freelance Writer | Personal Trainer

Frequently Asked Questions

How can I overcome my nervousness when talking to my crush for the first time?

Nervousness is common and can be managed by preparing mentally beforehand. Practice speaking with others to build your confidence. Also, remember that it’s okay to be a bit nervous—it shows you genuinely care about the interaction.

Is it okay to use humor when talking to my crush for the first time?

Yes, humor can be a great way to break the ice, provided it’s appropriate and well-timed. Make sure the humor is light-hearted and not at someone’s expense, which could create a negative impression.

How can I make a memorable impression during our first conversation?

Be yourself, show sincerity, and express genuine interest in what they have to say. A sincere compliment, a thoughtful question, or sharing a small but interesting anecdote about yourself can make the conversation memorable.

How can I make a memorable impression during our first conversation?

Be yourself, show sincerity, and express genuine interest in what they have to say. A sincere compliment, a thoughtful question, or sharing a small but interesting anecdote about yourself can make the conversation memorable.

What if my crush doesn’t seem interested in talking?

If your crush seems uninterested, don’t take it personally. They might just be having a bad day or not in the mood to talk. Be polite, end the conversation gracefully, and give them space. You might have a better chance at a different time.

Final Thoughts

Starting a conversation with your crush for the first time can be challenging, but it’s also an exciting opportunity. By using the tips and strategies in this article you’ll be on the right track.

Everyone feels nervous when talking to someone they like. The most important tip is to be yourself, stay positive, and focus on building a real connection. With a little practice and courage, you’ll be starting amazing conversations with your crush in no time.

Be brave, and see where your words can take you!

How useful was this post?

Click on a star to rate it!

As you found this post useful...

Share it on social media!

We are sorry that this post was not useful for you!

Let us improve this post!

Tell us how we can improve this post?

Photo of author

Erika Maniquiz is a certified teacher and librarian with a Library and Information Science degree. She cherishes the calm moments reading books as much as the dynamic discussions she has in her classroom. Beyond her career, she is a fan of Kdrama and loves Kpop's lively beats.