How to Start a Conversation With Your Crush for the First Time

It can be hard to strike up conversations with people, even if you might want to – especially when it’s someone you like.

That being said, here are a few tips from relationship experts to help you start a conversation with your crush for the first time.

Chris Pleines

Chris Pleines

Dating Expert, Dating Scout

Reference something he or she likes

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.

Show genuine interest

When we talk to the person we are attracted to, we tend to get nervous, fumble on our words, or worst, come out as aloof. The other party might dismiss you as someone uninterested or boring.

The best way to come across as interesting is by being interested yourself. Don’t ask the standard questions such as “Where are you from?” and leave it at that. Ask questions that generate more conversations such as, “What is it about that place that you like?” This allows your crush to give answers that propel you to other non-superficial conversations. The important thing is, to get the ball rolling right away.

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.

Robin Sutherns

Robin Sutherns

Relationship Expert | Editor, Galtelligence

Sometimes, when we’re crushing on someone, it can be a struggle to approach and talk to them. Our nerves get the best of us. We stutter. We never know what to say or what to do. It can be hard to approach and start a conversation with your crush, but with the right guide, anyone can do it.

Here are 3 tips to start a conversation with your crush:

Use the right conversation starters

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.

Don’t overthink

We get nervous because we overthink the exchange. We get ahead of ourselves. Don’t do it if you want to be successful. Don’t overthink anything and just go with the flow.

Find a common ground

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.

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.

Steffo Shambo

Steffo Shambo

Relationship Expert | Founder, Tantric Academy

Warm-up: Practice talking to people you’re not scared of

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.

Come up with stories you can easily fall back on

Once you’ve kind of broken that ice and have warmed up and asked some questions and talked to people you’re not scared of, talking to your crush will seem a little bit easier. You might be thinking “okay, cool! I can approach them and talk to them, but I don’t really know what to talk to them about.“

This is why 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.

It might help if you treat your crush the same way you treat your family member and close friends. You don’t have any issues being comfortable talking to your grandmother, and you don’t have any issues coming up with what to say to your grandmother. See if you can pretend your crush is your grandmother!

Only allow a maximum of 5 seconds to approach them

When you see your crush, give yourself no more than five seconds to walk up to them and to say something. If you stand around thinking about what you’re gonna say, you’re gonna freeze up.

A good mind-trick is to count backward from 5, and when you get to 1 just take action without thinking. You’re gonna come up with a million reasons as to why you can’t do it, but if instead, you’re focusing on that countdown, and you’re getting ready to just propel yourself, once you’re in motion, you’re doing it.

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.

So even if you just say something like “Hey, how’s it going?” or “hi” in general, that’s a success already. If you practice talking to people, if you have go-to stories that you can rely on, and then you push yourself to not overthink things at the moment and give yourself no more than five seconds to approach them, you’re gonna feel way more comfortable talking to your crush, especially when you’re nervous, especially when you don’t know what to say, especially when you think everything’s gonna go wrong.

You have what it takes to do this. Stop holding yourself back, and go for it.

Related: 7 Physiological Signs of a Crush

Alexis Wolfe

Alexis Wolfe

Dating Guru & Founder, NYC Date Nite

Smile and eye contact

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.

Start with a question

Don’t just say hi and have the other person take it from there. Start with a specific question that is easy to answer and gets the conversation going. Even something silly such as “what is your favorite NYC pizza spot” gets the other person thinking and can quickly turn into a seamless conversation about food, restaurants, cooking, etc.

Show or send a funny meme

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.

Respond to an IG story

This is an easy, safe, and more low-key way to show you’re interested while still making them work for it. You just made the subtle first move, let’s see if he/she takes the bait.

Chase Amante

Chase Amante

Founder, Girls Chase

Proximity first

Well, first thing’s first: you need proximity. Hard to chat your crush up from across the room. And it’s awkward doing it online (I know it feels less intimidating… but you really want to do it in person).

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.

Or you may not need one; ever notice how sometimes your crush just ‘appears’ next to you? Well… you can do that too. Grab a seat nearby, or post up in a spot real close. Act like you’re looking around a little bit and just ‘happened’ to find that spot.

Situational relevance

Once you’re there, you’ll need a reason to start a conversation.

Make a comment about the environment. Ask her how she did in that last test if you’re in class. Ask him if he’s figured out what he’ll order if you’re in line at the coffee shop. Ask her if she’s going anywhere exciting if you’re waiting for the bus or train.

Genuine compliment

You can either open with this, or add it after your opener. But often it’s helpful to make a genuine compliment. What’s a genuine compliment? It’s a compliment you give someone about something you genuinely like.

Does he have legitimately stylish hair? Tell him he’s got the trimmest hair you’ve seen all day. Did you take one look at this girl the way she’s dressed and go “Wow”? Tell her you love her fashion sense, and pick a piece, in particular, she has on you really enjoy.

Choose items your crush chose, rather than things your crush was born with. Don’t comment on facial features or hair type, for instance. But do comment on clothing choices, hairstyles, cool walks, neat accessories, and so on.

If all else fails, remarking on your crush’s “really nice smile” is always a good one (and my go-to backup for when nothing else springs to mind, personally).

A situational opener followed by a genuine compliment is often all you need to get into a really great conversation.

Cierra Loflin

Cierra Loflin

Chief Marketing Officer, Zodiac Guides

Ask for help

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. Another classic example is asking someone for a lighter, then following it up with another question.

Asking for a small favor, such as helping you with a work problem, gives you an excuse to talk to them.

It takes out the awkwardness of introducing yourself for no reason. It can also lead to a natural conversation when you follow up with another question such as, “How long have you been working here?”

May Bugenhagen

May Bugenhagen

Certified Professional Matchmaker | Owner, Matchmaker May

Be confident and start a sincere and genuine conversation

When you have a crush on someone, you might be tongue-tied or nervous. Keep in mind, there are more insecure people out there than you think.

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.

Sarcasm can make you seem like a negative person. One sure way to get the attention of someone you’re crushing on is this; start a sincere and genuine conversation.

How do you do that? Easy enough.

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. It’ll make you stand apart from others. It can be something casual about their hair.

If you like the way her hair looks, say so. “Your hair looks really nice. Is that your signature look? It should be.” If you like his sports jacket, say so. “That’s a really nice jacket on you. You have good taste.” And then smile for five seconds and hold eye contact.

If he or she is intrigued by you, they will continue the conversation. Then ask questions in the conversation. Everyone loves to talk about themselves!

Maxwell Kamlongera

Maxwell Kamlongera

Freelance Writer | Personal Trainer

Be “at the moment”

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.

To be “in the moment” you only need to keep in mind two very simple things:

  • Be aware of your environment.
  • Be aware of what’s currently taking place

These two things are necessary because they’re all you’ll ever need to start a conversation no matter where you are or what situation you’re in. Now, here is how they work and how you string them together:

Firstly, you want to be aware of the environment because your current location provides you with a conversational topic. This way, you don’t need to wrack your brain in thinking up a good ice breaker; your location is the ice breaker!

Next, you want to be aware of what’s taking place around you because that will provide the content of the topic.

Now, to put them together in an example. Let’s take a generic and boring location because it’s more challenging to make conversation out of a boring place and anyone can see/find themselves in a boring/generic location (the more unique a location is, the easier it is to use it as your ice breaker). So let’s use a grocery store.

Assume you bump into your crush at the grocery store. When this occurs you want to get your crush’s attention and there are two ways to go about this. You can either speak to the crush directly by saying “hi” followed by a simple observation that relates to your situation, or you can make a loud, outspoken comment meant to catch their eye and attention; if the crush looks at you, you use the opportunity to strike a conversation.

For example:

  • If you bump into the crush in an aisle, perhaps block the aisle with your trolley and yourself and when they need to pass by, apologize and make conversation about how much of a klutz you tend to be when you spot things on the shelf that grab your attention.
  • Or if you bump into the crush in a queue, loudly comment how people who check out so much grocery are just the worst (bonus points if you or the crush is currently guilty of this so you can use it as a cheeky way to start a conversation);
  • Or if the crush has on them a store item that you have a strong opinion on (preferably a positive, unique opinion), openly comment on what you think of such people who use the product and why – this should illicit a reaction and you go into conversation from there.

What all the above scenarios have in common is that they rely on what’s currently taking place in front of you, hence the mantra to be “in the moment”. It’s as simple as that, and it doesn’t need overthinking.

And if you’re nervous, give this a test run on random strangers when you go out and use those moments as opportunities to practice so you’re fresh and ready when you eventually try with your crush.

With all this said, you can make an encounter with a crush 10x easier and less nervewracking if you already have a location you typically spot your crush at. This means you don’t need to think on your feet when trying to start a conversation as you already know what about the environment you can use to start your conversation!