15 Ways to Start a Conversation With a Guy Over Text (+ 4 Ways NOT to)

how to start a conversation with a guy over text

So you swiped right on a dating app and matched up with a guy. Maybe you’re on Bumble, where the ladies have to start the conversation. Or you want to text a man you met through a friend. Whatever the situation, now you want to know how to start a conversation with a guy over text.

What You Need to Know About How to Start a Conversation with a Guy Over Text

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 that LANDLINE for his call?!)

Even if you consider yourself fairly savvy at texting your girlfriends (you’re known as the GIF user 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:

  • Getting the party started
  • Keeping the conversation flowing
  • 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 are a few tips to ensure that he eagerly responds to that first text you send.

1. Do More Than Say “Hey.”

You’re a smart lady, so why would you waste valuable texting real estate with a totally dumb starting line?

Nearly 30% of 18-24-year-olds are totally 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.

2. Get 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. 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? 😨

5. Time Your Text.

Realize that you might, without meaning to, communicate desperation with your text depending on what time you send it. Texting for the first time on a Friday evening at 8 pm might tell him that you’re a bit desperate for a date.

Texting first thing in the morning can be overwhelming too…or even wake the guy up. Aim for after work, maybe around 6 on a weekday, for the best shot of getting a reply.

Once You Get Rolling

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 if you’ve asked several in a row without him having a chance to ask his own.

7. Pay Attention to Whether He Asks Questions.

If he doesn’t ask many questions, he’s not interested.

It’s a red flag if you’re the only one who’s curious and asking questions. One way to make him realize that you want to feel like he’s trying to get to know you is:

“Sorry for all the questions! I’m just naturally curious. It’s your turn to ask a few!”

If he doesn’t bite after that, he probably isn’t interested enough to put any effort into getting to know you. Move on.

8. Watch That 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 Words Out.

U r nt a teen. Dn’t txt lyk 1.

Grownups spell words out. For Pete’s sake, you’ve got “voice to text”, so how lazy can you be?

Realize that if you use abbreviated words or even bad grammar or punctuation, you might be judged by the man you’re texting: 75% of men judge bad grammar.

How to Show Interest

Let him know you’re into him!

Once you realize that you’re hitting it off, make sure you let him know that you’re interested in your texts 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. Call Him By His Name.

It’s subtle, but calling this guy by his name in the text (or later, by phone or in person), communicates your interest.

You can also call him endearing terms like:

  • Cutie
  • Honey
  • Hotstuff

11. Give Him Your Number.

If you’ve been texting through a dating app, step up your game and give him your phone number. This tells him that you like him enough to move to the next step in this game. A date won’t be far behind.

12. Ask Questions That Show Interest.

Everyone feels good when someone shows interest in what they do and care about! If he told you yesterday that he was going to watch the game, ask who won.

Ask what he likes about his job.

Ask what he’d do if money were no issue.

Ask how his work presentation went.

Ask how his friend that broke his arm is doing.

Essentially, you want to show that you’re paying attention to what he’s saying and that you care enough to retain that information.

13. 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.

14. Flirt a Little.

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…

…or ask him for a photo…

…if you’ve gone out, you could tell him you can’t wait to see him again…

It may not come naturally at first, but with a little practice (give my Flirting Workshop a try), it’ll become second nature.

15. Use Emojis.

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

😚 😘

These kissing emojis makes 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.

How NOT to Start a Conversation with a Guy Over Text

Now that we’ve covered how to start a conversation with a guy over text, as well as how to express your interest in him, let’s cover a few no-nos in texting.

Bombard Him with One Text After Another.


Unless you want him to ghost you, let him respond before you send another text. It will require patience, but trust me on this.

There’s a woman in Arizona who sent a man 159,000 texts (and stalked him) after just one date! Don’t be that woman!

Pout if He Doesn’t Respond Immediately.

Clearly something is wrong if he doesn’t respond within a few seconds. Right?


You may be wrapped up in the fantasy of this guy doing nothing but thinking about you all day, but in reality he’s probably working, running errands, sleeping…or just not available. Don’t assume the worst. Again, have a little patience.

Go Too Deep Too Soon.

Work, hobbies, interests are all acceptable topics for early texts before you’ve gone out. Save the relationship history, politics, and religion for later.

Signs You Should Move On

A lot of 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.

Let me give you a few signs to look out for.

It’s All Text and No Movement Forward.

Texting is great, but if you’re doing it for a week or more, you risk turning into pen pals. Sure, some guys are slower than others, but if he’s not asking about your schedule or whether you have plans for the weekend, he might not want to meet.

You can, of course, take initiative and ask him out. That way you can at least see if he’s interested.

He Seems Permanently Unavailable.

If he can’t or won’t meet, he might be catfishing you.

If this guy travels a lot or is out of town for an indefinite period of time, you’ve got to first ask yourself why he’s on a dating app. If he can’t meet, what’s the point?

Also, realize that a man who is this unavailable may also be catfishing you. That’s not necessarily the case, but be aware that some men (and women) create fake profiles with the objective of messing with your head or just because they’re bored.

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.


Even if this doesn’t end up being your Prince Charming, you at least got practice on how to start a conversation with a guy over text!

It’s like any skill: the more you do it, the better you get at it. Just keep it light and have fun with it.

And if things do work out, you’ve successfully learned how to use another communication channel that maybe you didn’t use when you were last single decades ago. Texting can be a great asset in a relationship!

how to start a conversation with a guy over text

Adam LoDolce

Love Strategist

My true passion in life is transforming your love life by giving you specific tools and techniques that you can use to attract long lasting love. I got started when...Read Adam's Story

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1 year ago

Hi , i´ve been seeing this guy for 3 month .I asked him if he seeing other people.he told me he fills to young to be in a realationship.he still calls me want to hang out or go hikes or go to comedy show what should i do with the young guy?

1 year ago

Wow,nice one.
For some time now i think i have found a way and have learned that this guy is not interested n have to move on.
Thanks sir Adam for this article and be blessed.

1 year ago

Thanks for sharing such a good piece of information.!!

1 year ago

Wow this amazing hoping to learn more thanks

11 months ago

Meet a guy l like but he seem uninterested he does reply my messages though and sent me the most touching music however it goes no further than texts spread through days.

9 months ago

Thank you for very good advice of how to make a man chase you.by not being to available

9 months ago

Hi, thank for sharing such a nice post on your blog keep it up and share more.

8 months ago

Hi so i just started the into wanting a date for the 1st time and i don’t know how to text a guy at all can i get coached cause I’m nervous about it

5 months ago

My Friend is really nice and all but he gives me some signs. So we started to flirt but I hate making the first move. What do I do? I don’t want to mess up our friendship but I really like this guy.

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