How To Start A Conversation With A Guy (Over Text & IRL)

Maybe there’s a gorgeous man you keep bumping into in real life, or you just signed up to a new dating app, and you’re ready to kick-start your love life again. There’s only one snag. You have no idea how to start a natural, engaging conversation with a guy.

Don’t worry; you’re not alone.

This is one of the biggest blocks with the women I coach.

You want to meet new guys and start dating again, but your confidence isn’t quite there, or it has been a hot minute since you even thought about putting yourself out there again.

And I get it. Whether you’re trying to figure out how to make conversation with a guy in person or how to start a conversation with a guy online, the thought alone can fill you with anxiety—especially if you think he’s smoking hot. You want to be cool and confident and sexy, but past experience tells you it never quite works out that way for you in real life. Nerves get the better of you, and you either end up chickening out altogether or saying something that doesn’t even make sense.

Sound familiar?

But y’know what?

We all start out like this (me included).

And the only way you get really good at something is to learn from experts, practice, and repeat.

The first step to start a conversation with any guy is to embrace rejection

In my experience, the number one thing that holds us all back when it comes to pretty much everything is a fear of rejection.

But here’s the deal: if you spend your entire life avoiding rejection, you won’t do anything, you won’t have anything, and you won’t achieve anything. Because rejection is a part of life. It might stir feelings of pain and shame within us when it happens, but it won’t kill us.

Author and entrepreneur Jia Jiang actively sought out rejection for 100 days, and he discovered the magic of what happens when you put yourself out there and pursue what you want.

So if it’s a fear of rejection that is holding you back in your love life (and everywhere else), I invite you to lean into that with me.

Will it be scary?

Probably.

Will it be worth it?

Hell yes.

Here’s how to start a conversation with a guy over text or online

If you’re getting back into dating after a long break, you might be shocked at how important texting has become in dating. You’re much more likely to text someone you’re seeing than talk to him on the phone, at least early on, so be ready for that shift from the way things were the last time you dated. Remember waiting by the LANDLINE for his call?!

Even if you consider yourself reasonably savvy at texting your girlfriends (you’re known as the GIF Queen in your group), realize that you still need to know how to start a conversation with a guy over text and keep his attention. Because it’s a bit different from how you’d interact with your friends.

Let’s break down your texting into three sections:

1. How to start a text conversation with a guy
2. How to keep a conversation going with a guy over text
3. Letting him know you’re into him

That first text is so important. Whether you’re too impatient (or confident) to wait for him to text you first, or whether you have his number and he doesn’t have yours, you’re up to bat, so you want to make sure your text is engaging, witty, and intriguing so that he’ll text you back.

Here’s everything you need to know on how to start a conversation with a guy you like over text.

1. Do more than say “hey”

You’re an intelligent, one-of-a-kind lady, so why would you waste valuable texting real estate with a totally mergh starting line?

Nearly 30% of 18-24-year-olds are cool with “hey” as an intro text. But you’re not in that demographic, are you? Go with something that requires a bit more intellect and requires a response from him.

Be authentic. Be creative. Say what’s on your mind. Say something that you would want to reply to.

Here are some interesting conversation starters for texting to get you going:

• If you had to describe yourself in three words, what would they be?
• What are you grateful for today?
• Send me an emoji that sums up your day

2. Start a conversation with a guy by getting inspiration from his dating profile

If you’re on a dating site, read his profile and find something you can ask a question about (questions require an answer and keep the conversation going!).

You might see a photo of him at the top of a mountain:

“Looks like you’re into hiking like me! What’s your favorite trail?”

Or his profile might say he speaks four languages:

“4 languages, huh? Parlez-vous français? Parli italiano?”

Some dating sites have icebreakers, like having the user list two truths and a lie:

“I’m going to guess that your lie is…rescuing a baby tiger from the clutches of a bear. Am I right?!”

3. Text only when you have time to respond

Ping!

You get a notification on your phone that you’ve matched with a man. You’re eager to get the conversation started. But don’t do it unless you can instantly reply and hold a conversation should he respond immediately.

You’re more likely to launch a text conversation if you respond promptly to his reply. Otherwise, he might lose interest and find another woman to text.

4. How to start a conversation with a guy on text? Make him laugh

If you can pull off funny, it’s a great strategy to start a conversation with a guy over text.

“OMG! I was typing to ask if this was the only paid dating site you were on, and autocorrect made it ‘pain dating site!’ Oh my! I don’t think it’s that kind of site…do you? 😨”

Send a GIF or Meme along with a short caption that is guaranteed to make him laugh out loud and move the conversation in a fun direction. Or ask him what his favorite Meme of all time is.

Humor is a brilliant text opener because you’re giving him something entertaining to respond to.

5. Time your text

Realize that you might (without meaning to) communicate desperation with your text depending on what time you send it.

For example, texting for the first time on a Friday at 8 PM might tell him that you have nothing remotely exciting going on.

Texting first thing in the morning can be overwhelming, too—plus, there’s a small chance you might wake the guy up!

Aim for after work, maybe around 6 PM on a weekday, for the best shot of getting a reply.

Next up: How to keep a conversation going over text with your crush

So, you’ve mastered how to start a conversation with this guy. Now that he’s responded and you’re texting back and forth, how can you keep the conversation going?

6. Focus on getting to know him

Now is the time to ask questions so you can determine whether this guy is a good fit and potential suitor. But don’t bombard him with questions! Keep a healthy mix of questions and comments.

Try to give him a chance to ask you questions in return. While there doesn’t have to be a 1:1 ratio of text questions (women tend to be more curious than men, I’ve found), back off a little if you’ve asked several in a row without him having a chance to ask his own.

7. Start and hold a conversation with a guy by asking open-ended questions

If you’re wondering how to start and keep the conversation going with a guy via text, the secret is to ask questions that require more than a one-word answer.

A classic question to ask someone is, “how was your day?”

The problem with this is, it usually receives a response like, “okay,” or “good,” or “fine.”

This is because it’s a generic question, and it doesn’t force him to think about his answer or elaborate.

An open-ended question is a question that cannot be answered by a simple yes or no.

For example:

• What’s your biggest goal in life?
• What was the best part of your day today?
• If you could only eat one type of food for the rest of your life, what would it be?

8. Pay attention to tone

The thing about text messages is that sometimes they can be misinterpreted. What might have been a sarcastic and witty comment in your head could come out snarky and mean.

Always read your texts before you send them, and ask yourself whether someone who didn’t know you well might misunderstand your intention. If there’s even a shadow of a doubt, rewrite the text.

9. Spell like a grown-up!

U r nt a teen. Dn’t txt lyk 1.

Grown-ups spell words out. For Pete’s sake, you’ve got “voice to text,” so how hard is it to spell out words correctly?!

Realize that if you use abbreviated words or even lousy grammar or punctuation, you might be judged by the man you’re texting before he even gets to know you. Stats show that 75% of men judge bad grammar. And let’s be honest here—most women feel the same way.

Finally: How to subtly let him know you’re into him over text

Once you realize that you’re hitting it off, make sure you let him know that you’re interested so you can get that first date scheduled.

Because you’re interacting via text, it can be harder to communicate interest than it would be in person, so use these tips to get it right.

10. Text him throughout the day

Think about how you feel when a man texts you to wish you good morning each day or makes a point to say “good night” via text.

It feels good, right?

So do the same to let this man know that you’re thinking of him.

Here’s the only caveat: stop doing it if he’s not reciprocating. If you look at your text chain and see that it’s been mainly you popping in to say hi, back off. If the texts aren’t more back-and-forth, he may not be interested.

11. Flirt

One surefire way to let a man know that you’re into him is to flirt. There’s no need to go overboard, but make sure he knows you want more than just being friends.

You could:

• Send him a selfie where you’ve got a sexy smile
• Ask him for a photo
• Next time you’re delayed replying to him, say, “sorry, I just got out the shower…”
• If you’ve gone out, you could tell him you can’t wait to see him again

12. Use emojis

Emojis aren’t just for teenagers! A carefully chosen one can express more than words.

😚 😘

These kissing emojis make it clear that you’re interested!

😊

If he compliments you, you can always blush!

😍

If he says something that makes you even more gaga about him, use this one.

13. Don’t hide behind your phone

Texting is a great way to connect with someone new and see whether there’s any potential for a relationship. However, you can’t build a deep connection without speaking to someone on the phone or meeting them in real life.

So, if things are going well over text and you’re keen to take things further, ask him to call you or arrange a date.

Here’s a great way to get him to call you next time you’re texting:

“I’m kind of slow at typing… call me?”

Some guys are a little shyer than others when it comes to asking women out. But if weeks go by and he’s not willing to have a video call with you or meet up, this is a potential red flag that he’s not who he says he is, or he’s not interested in pursuing things.

Here’s how to start a conversation with a guy IRL

Although many new connections happen via text, social media, and dating apps these days, there will still be plenty of opportunities where you meet an attractive man in real life.

How to start talking to a guy in person requires a little more confidence than it does via text. There’s nowhere to hide, and you’ve got less thinking time to respond.

That being said, it’s still a brilliant way to meet new guys. What man doesn’t enjoy having his day interrupted by a beautiful stranger?

If it turns out he’s already taken or not interested, you’ve not lost anything. And who knows where it might lead?

1. Compliment him

Have you ever had a random stranger stop you in the street and tell you, “I love your outfit,” or “you look beautiful in that dress,” or “you have an incredible smile”?

If you have, you’ll know how AMAZING it feels. It’s not weird in the slightest. It’s wonderful. And you appreciate it that much more because it’s coming from a total stranger—and it took courage for them to put themselves out there like that.

This is also a great way to start a conversation with a guy in real life. Pick something you love about him—his jacket, his eyes, his headphones, his cologne, his choice of sandwich at the deli—and tell him. It is guaranteed to make him at least smile and potentially stop and chat more with you.

2. Bring up the book he’s reading

Wondering how to start a good conversation with a guy in a coffee shop, on a train, or in a bookstore?

Talk about the book he’s reading!

Of course, this only works if he is reading a book (duh), but if you’re in a library or bookstore, chances are good that he will have a book in his hands.

You might have already read it or read something in a similar genre and can mention what you thought about it. And if not, ask him whether he recommends it—say you’re looking for something new to read.

3. How to start a conversation with a guy: Ask a small favor

Ask for directions in the street, ask him to hold the door open for you if you’re carrying something heavy, or ask him to get something down from the top shelf in the grocery store.

Just be careful not to overdo it and act helpless—you don’t need to hide your strength. It’s not about acting like a damsel in distress. It’s about letting him lean into his masculine energy and feel like he’s helping you. Men are biologically wired to want to do this. And you get to tap into your feminine energy, which is part of Little Love Step #1.

If he does help you, thank him, smile, and don’t be afraid to keep the conversation going.

4. Surprise him by paying for his drink

You can do this at a coffee shop or in a restaurant or bar.

When you get to the till let the sales assistant know you want to pay for whatever that guy (ahead of or behind you) is having. Send him over a drink in a bar and tell the waiter to let him know it came from you.

Everyone loves the surprise of a stranger doing something generous for them. At the very least, he’s going to come up to you and say thank you.

5. The bold way to start a conversation with a guy: Introduce yourself

Okay, so this one’s not inventive in the slightest, but it works.

If you meet a guy in real life who catches your attention for all the right reasons, then trust in the simplicity of approaching him and saying hi, introducing yourself, and asking for his name.

If he’s into you, he’ll be excited to continue the conversation with you.

I know a few guys who have tried this out while shopping at the grocery store, and nine out of ten times, it works for them. So surprise him by making the first move.

6. Say his name (if you know it)

This tip works well if the guy is a barista, waiter, or sales assistant with a visible name tag on his shirt.

We all love hearing our names. It’s much more personal, it feels like the person knows us, and it’s just a warmer way to speak to someone.

Another cute way to get his name in a coffee shop is when he asks for your name to write it on your cup, fire the question right back at him!

7. How to start a conversation with a guy: Make his dog the star of the show

I honestly don’t know why more single women are not hanging out in parks because a man walking his dog is the EASIEST conversation starter of ALL TIME.

If his dog pads over to you, give him a stroke (as long as you’re not afraid or allergic).

Ask the guy what the dog’s name is or what breed it is. People love talking about their pets.

If you have a dog, too, this will be even easier. There’s always the option to borrow someone else’s dog and walk it—this might make you feel more comfortable about the whole thing and less of the weird-woman-staking-out-guys-and-their-dogs-in-the-park vibe.

8. Ask him for a recommendation or opinion

This one lets him lean into his masculinity again by allowing him to help you out with something.

If you’re new to the area, a great way to start a conversation with a guy would be to let him know you’re new in town and ask him for his list of the top things to do there.

If he mentions something that sounds like your thing, be enthusiastic about it, and who knows, he might ask you out.

Alternatively, you might say something like, “I’ve been meaning to check out the art exhibition on X street—do you think it’s worth a visit?”

9. Start a conversation with a guy by sharing something real with him

One thing you don’t see enough of these days is authentic conversations between strangers. We’re all so stuck in our heads and afraid to be vulnerable that we end up talking about the most mundane things that even we couldn’t care less about.

A great example of this is the weather. Why do we talk about the weather so damn much?

Do you care about what’s going on with the weather?

Because if you don’t, chances are he doesn’t either.

The secret to how to start a conversation with a guy lies in being authentic. Share something real with him. If the moment feels right, tap into your heart and be honest about what’s on your mind.

There’s a fine line between being authentic and over-sharing too soon, but when you get it right, this can instantly spark a connection.

Signs you should move on

Many women I’ve coached get frustrated that they’re not better at reading the signs that a man isn’t interested. It can be challenging to watch for those cues, particularly if you haven’t been single that long.

So, when you start a conversation with a guy but you’re not sure how well things are going, here are a few signs that he’s not that into you, and it’s time to shout NEXT.

He never texts you first

A woman making the first move is powerful. But if you initiate a conversation with him every time, it’s a sign he’s not that interested in pursuing things.

He’s hot then he’s cold

Do you have back and forth texting marathons some days, then not hear from him for days or weeks at a time?

This is classic hot and cold behavior, and it’s a MAJOR red flag. This guy is either dating someone else already, emotionally unavailable, or not interested in a relationship with you. Either way, it’s not good, and you deserve someone who wants to give you a text back.

He only texts you late at night

Late-night texts from a guy between 9 PM and 3 AM are almost always about sex. He wants pictures, he wants you to come over to his place, or he’s bored out of his brain.

If you keep receiving texts from him late at night, ask him why he never texts you in the day.

Unless he’s a vampire or works night shifts, there’s no excuse.

He’s taking the conversation sexual too fast

You’re not a prude, but jeez, you’d like to meet a man before sexting. If this guy is making you uncomfortable, block him. There’s no reason why a man should make sexual overtones too soon, especially if you’re not reciprocating.

He’s not asking you out

As I’ve mentioned already, you can only talk to a guy for so long before you either go on a date or move on.

If he’s interested in pursuing a romantic relationship, he will ask you out sooner rather than later.

So if he’s not making any plans, then there’s a strong chance he doesn’t see you that way or is already seeing someone else. Bite the bullet and ask him out yourself. Embrace rejection. The worst that can happen is he tells you he’s not interested, and you can then move on.

That’s how to start a conversation with a guy online, via text, or in-person

Learning how to start an interesting conversation with a guy you’re attracted to, and keep the conversation going, takes practice. It’s normal to feel anxious, nervous, or intimidated when you first start approaching guys this way. But the more you put yourself out there, the easier it will become, and although you might not believe me when I say this—it won’t be long before getting to know a new guy becomes fun. Outrageous, I know, but this whole dating thing is meant to be fun!

Don’t get caught up in sending the perfect text or rehearsing lines to say to a guy in real life. Relax. Focus on being authentic and playful and forget about the result. Whether he’s into you or not is not the goal here—the goal is to get comfortable and confident starting conversations with men. Because one of them might just turn out to be the love of your life.

I’d love to hear about some of the ways you’ve started a conversation with a man you didn’t know, on a dating app, via text, social media, or in real life. Let me know in the comments below.