How to Start a Conversation with a Guy (IRL, Text & Online)

Starting a conversation with a guy you like can feel super awkward, whether it’s in-person or online.

In general, you might be quite a confident person, but when it comes to opening a conversation with your crush, you turn into a nervous wreck.

You’re not sure how to approach that first conversation, and you’re not even sure that guys like it when girls make the first move. These doubts have been putting a real dampener on your dating life.

But do you want to know the good news?

Men who were asked what they thought about women reaching out first had only positive things to say. In fact, they admitted that they love it when women are direct and open about their interests from the get-go.[1]

With this reassurance, let’s get into some tips for how to start a conversation with your crush in person and over text. Think of this article as your guide to go from nervous and awkward to confident, flirty, charming, and fun in no time.


  1. How to start a conversation with a guy you like in real life
  2. How to start a conversation with a guy you like over text
  3. What not to do and say over text.
  4. Common questions.

How to start a conversation with a guy you like in real life

Is there a handsome stranger you’ve been eyeing up for a while? You’d love to talk to him, but you haven’t been able to think of a great conversation starter. Maybe there’s a guy you like and have known for some time, but you don’t know what to say to let him know you’re interested. Or maybe you just want to know what to say when you cross paths with any cute guy in the future.

The great thing is that if a boy is into you too, it won’t take much effort on your part to keep the conversation going once you’ve made the first move. The exception is if your crush is more on the quiet side. But don’t worry, because when we answer some common questions, we’ll tell you how to talk to quiet guys, too.

Here are our 8 top tips for how to start a conversation with a guy you like in real life.

1. Ask him for advice or for his opinion

This tip can work whether you’re starting a conversation with a guy you like for the first time or with a guy you already know.

If you’re asking for advice from a guy you haven’t spoken to before, use your environment to help you think of what to ask him. If you’re at the mall and you’re both looking at home decor, ask for his advice on a new rug you plan on buying.

With a guy that you like and already know, you could ask for his opinion on something that you know he is passionate about. If he loves fitness, ask him for advice on the best protein supplement to buy.

2. Ask him a favor

This is an easy way to open up a conversation with a guy you like in a subtle way. If you want to talk to the boy you like but you’re scared he will reject you, give this a try.

For a guy that you are talking to for the first time, you could ask him for something very small, like what the time is, or to help you operate the self-service coffee machine.

For a guy you know a little better, you could ask a bigger favor. If you know the guy you like is a statistics nerd and you have been struggling in your statistics course, you could ask him to tutor you.

3. Use the environment

Take advantage of what is going on around you as a way to start a conversation with a man you like. When you zone into your surroundings, you will find that there are so many things you can talk about.

If you’re at a coffee shop and waiting in the queue behind a cute guy, make a comment on a new beverage or pastry that’s advertised and ask him if he’s ever tried it.

If you’re out and about, you can use the tried and true topic: the weather. Is the sun finally shining after many days of rain? Then you could open up the lines of communication with something like, “Aren’t you glad the rain has finally cleared up?”

4. Ask him about his puppy

If you want to use an easy conversation opener with a cute guy, then head to the park and see if you can spot a cute guy with a dog!

Starting a conversation with someone about their dog is one of the oldest tricks in the book, and people love talking about their pets.

Be super curious about his dog. Ask him things like the dog’s name and breed and how long he’s had the dog for. If you have a dog too, you could let the dogs sniff each other out. If they seem to like each other, use that as an opportunity to organize a doggie “play-date” and as a chance to meet up with your crush again.

5. Compliment him

It is charming to have someone notice something about us and bring it to our attention. Being on the receiving end of a compliment makes us feel good inside, no matter which gender we identify with.

So if you’re feeling bold and brave, complimenting a man is a great way to open up a conversation and show him that you like him.

A less intimidating way to give a compliment to a man is to compliment him on something he is wearing. You could tell him that you really like his Converse sneakers. If you want to be even more direct about your attraction to him, compliment him on a unique physical attribute like his gorgeous smile or his dimples.

6. Introduce yourself

It may sound simple, but it works! Simply treat the guy you like as you would any other new person you would introduce yourself to.

Approach him with a warm and friendly smile and say, “Hello, my name is ______. What’s your name?” you could even add, “I’ve seen you around here quite often, so I thought I’d introduce myself.”

If he likes you back, he will be more than happy to carry the conversation from the first introduction.

7. Revisit a previous conversation

Revisiting a past conversation works well if you have already spoken to your crush before.

Here’s an example:

Perhaps the last time you spoke to your crush, you were exchanging notes about what series you each like to watch. Let’s say he told you about an interesting documentary that he had watched and he recommended that you watch it, too.

If you watched it, then the next time you see him, go back to talking about the documentary as an opener. Let him know whether you agree that the documentary was great or whether you hated it!

8. Accept that rejection might happen

Maybe the fear of being rejected by your crush has been preventing you from making the first move. Rejection hurts, so it’s normal to feel anxious about putting yourself out there.

One way to solve this problem is to look at the costs versus the benefits. If you don’t make a move, the cost is that you could miss out on developing a great relationship. The benefit of not making a move is that you definitely won’t be rejected.

What is more important? Discovering a potentially great relationship, or the risk of rejection?

Try reframing how you view rejection. Think of each rejection you get as leading you one step closer to the person you’re meant to be with.

How to start a conversation with a guy you like over text

Is there a guy you like who you are already connected to through social media apps like Instagram, Snapchat, Twitter, or Facebook? Maybe you have liked him for a while, but he’s always had a girlfriend. You’ve decided now would be a great time to reach out and start a conversation over text, but you’re not sure how.

Or perhaps you’re using an online dating app, like Tinder or Bumble. You’ve already matched with a few cute guys, but you don’t know how to initiate the first conversation or what to say to make the conversation flirty and fun.

Here are our 7 top tips for how to start a conversation with a guy you like over text:

1. Be creative

In the online dating world, rejecting someone is as easy as swiping your finger left or right or clicking the “block” button. There’s no accountability when you’re behind a screen.

When connecting with other singles is this easy and this accessible, and passing on them is just as easy, it’s important to think about how to stand out. Saying a simple “hey” might work wonders to catch the attention of a boy you like in real life, but over text? BORING.

Instead, use a clever conversation starter that engages the guy you like enough to make him actually want to reply.

For example:

  • “If you could be an animal, which one would you be and why?”
  • “Are you a pizza guy or a pasta guy?”

2. Comment on something from his profile

There must have been something you noticed in the dating profile of the guy you like that piqued your interest to begin with. Besides his good looks, of course.

Commenting on or asking questions about what appeals to you from his profile will show him that you’re interested in getting to know him better. It’s also a great way to bond over common interests.

Maybe you were intrigued by his traveling photos taken all over the world. Or perhaps you liked something he wrote about himself.

Here’s what you could say:

  • “Is that photo taken in Munich? I’ve always wanted to go. How was it?”
  • “You wrote that your spirit animal is a dolphin – that’s mine too!”

3. Send a funny GIF or meme

If you’re texting a new guy who you’ve matched with on an online dating site or app, send him a funny meme or GIF along with an engaging question or comment. This will make him laugh and will show him that you have a sense of humor and that you’re fun to be around.

You could send a meme with the caption “current mood,” encouraging him to ask for details. Or you could send him a GIF and say, “Am I the only one who finds this hilarious? LOL.”

If you know the guy a bit better, send him a meme or GIF that relates to his interests. If he likes golf, you could send him a funny GIF of a golf swing gone wrong.

4. Ask open-ended questions

If you want to start a conversation that does not end before it has a chance to begin, then you should ask the man you like an open-ended question.

If you ask closed-ended questions or questions that just require a “yes” or “no” response, like “Do you like sports?” or “How was your day?” then the conversation can die out quickly.

When you use open-ended questions, the other person is forced to expand on their answer. So, you end up talking to them more, and the conversations get much more interesting.

Try some of these:

  • What kind of sports do you enjoy?
  • What was the highlight of your day?
  • If you could take a vacation right now, where would you go?

You might like to take a look at this list for more examples of open-ended versus close-ended questions.

5. Be playful and flirty

Guys are very responsive to playful banter. If you want to let a guy know that you like him as more than a friend, then use a cheeky conversation opener that makes it clear you’re being flirty.

Here are some example texts you can send to let the guy you like know that you’re interested:

You can use this one-liner on a guy friend who isn’t aware that you like him: “You actually looked really good tonight, you should take a shower more often!”

And here is one you could use on a guy you matched with online to encourage him to finally ask you out: “I’m really craving some chocolate ice cream…and a cute guy to eat it with!”

6. Be intentional

Getting the same “what’s up?” or “how are you?” text every day can become old very quickly. If you want to keep the guy you like interested and intrigued, you should start conversations that are more meaningful.

You can do this by thinking about what the point of the conversation will be before you text the guy you like.

How about sharing something exciting that happened in your day to build closeness.

Or you could ask him “would you rather” questions to spark an interesting debate.

Here are two examples:

  • “Would you rather have a pause or rewind button for your life?”
  • “Would you rather travel 200 years back in time or 200 years into the future?”

7. Refer to pop culture

A safe and reliable way to start a conversation with a guy over text is to talk about pop culture. Almost everyone has a favorite TV series they like to watch, movie genres they prefer, and books they enjoy reading.

So, open up your next text conversation by asking him, “Are you watching any good series at the moment? I just finished watching the last season of Stranger Things, and I’m looking for some new recommendations.”

Now he has an idea of the kinds of series you like to watch, and you can find out more about what he likes, too. What started as a simple question could start a larger conversation around what each of you like when it comes to pop culture.

What not to say and do when texting a guy you like

It’s just as important to know what you shouldn’t say and do when texting a guy you like as it is to know what you should say and do.

Here are 3 top mistakes to avoid when talking to your crush over text.

1. Avoid very serious questions

It’s tempting to start a serious conversation over text when you’re excited to get to know your crush on a deeper level.

But it’s important that you don’t start a conversation over text by asking him a loaded question. Avoid asking him things like what he thinks about the meaning of life or about his biggest regret in a past relationship.

It is difficult enough to convey our thoughts about such deep topics in real life, never mind over text. Communicating over text about complex topics increases the risk of misunderstandings.

So be wise and reserve personal questions for in-person meetings.

2. Don’t hide behind your phone

It might feel safer talking to your crush from behind a screen, but using text only to communicate will not deepen your connection. Besides, waiting around for a guy you like to finally ask you out can be frustrating.

Here’s how to drop a hint and get him to make the next move:

If he asks you a question that requires a longer answer, you could say, “I think this answer deserves a call, are you free in the next hour?”

Or, if you want to be even bolder, you could say, “Interesting question, I’d love to tell you all the details. Actually, I have a few questions for you, myself. How about we have this discussion over coffee?”

3. Don’t ask lots of questions

It’s important that you don’t make the guy you like feel smothered with loads of questions. Getting to know someone we’re interested in can be very exciting, and we want to know everything about them! But remember, getting to know someone is a process.

If you ask him too many questions, it will start to feel like more of an interrogation, especially if he is not asking questions back.

When he answers one of your questions, don’t immediately ask him another one. Instead, respond with a comment, and give him some time and space to ask you something next.

Here’s an example of what an exchange may look like:

You: Are you reading any books at the moment?

Him: Yes! I’ve been reading a book called “The 7 Habits of Highly Successful People.”

You: That sounds very inspirational. I’m a big fan of personal development books, too.

This comment gives him something to be curious about and puts him in the position to ask you a follow-up question if he wants. If he is interested in you, he will probably want to know what kinds of personal development books you have read.

Common questions

How do I start a conversation with a quiet or shy guy?

Make him feel comfortable by introducing yourself to him with a warm smile. Ask him for something small, like whether you can borrow a pen. Keep the first conversation short. The next time you talk, find out what his interests are. He will feel more confident talking about the things he likes.

Do guys like to be texted first?

Yes. Because guys are traditionally the ones who have had to text girls first, many of them like it when a girl takes the initiative and shows her interest by texting first. They like this direct approach.

Should you text a guy everyday?

It depends. Has there been an equal amount of back and forth texting between you? Does he ever text you first, or is it always you reaching out first and sending multiple messages a day? If you get into the habit of texting him everyday and he is not matching your efforts, it can look clingy.

Why do guys start texting less?

He may have a lot going on, or he may have lost interest. Gently nudge him and say, “You’ve been quieter than usual lately, are you okay?” If he responds, take his word but give him space and let his actions speak for themselves. If he really likes you, he will not stay silent for long.

How do you know if a guy isn’t interested through text?

You won’t see much effort from him. He may not respond, or he may take over 24 hours to reply. When and if he does respond, his replies are short and curt and lack any flirty, funny, or charming undertones. He never asks you any questions back, and he only texts you when he needs something.

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Kirsty Britz has a Master’s degree in Psychology from the University of New York in Prague, Training in Person-Centered Counselling, and a Career Coaching Certification. Read more.

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