What to Text a Guy To Start A Conversation: 29 Tips to Hook Him Hard

Want to know what to text a guy to start a conversation with him, or ask him out on a date subtly? Here are all the tips and examples you need to hook him!

How can you be sure if you like him if you can’t actually talk to him? Learn what to text a guy to start a conversation and go from there! 

Gone are the days of waiting for a man to approach you and make a move. Women are becoming more and more confident in their abilities to ask a man out when they want to. Women are making all the first moves nowadays, and we have to say, it rocks! But that doesn’t make it easy. You might still need some help knowing what to text a guy to start a conversation.

Even the most confident women can struggle to come up with something clever or cute to say. Something that makes this a lot easier is doing it over a text message, but that doesn’t take away the hardship.

You want to be flirty but not overly so. And you want to be clever but not too sarcastic. How do you find the balance and decide what to text a guy to start a conversation?

[Read: The 35 best text conversation starters for the shy and socially awkward]

Why that first conversation is so important

Let’s take the crushing part out of it for now. Forget that you want to go on a date. Try to push aside the idea of asking him out. First, see him as a person that you want to start a conversation with and get to know. Because, you never know, maybe after talking to him for a little while, you decide that you really don’t want to embark on that first date after all!

So, you need to try and start a conversation full stop. You need to text him, get chatting, and see where it leads. Sure, that can be hard when you’re super attracted to the guy, but remember, it’s about personality more than anything else.

If his conversation is no good, the rest is not going to be any good either. [Read: How to talk to people in a charming way no matter who they are]

What to text a guy you have your sights set on

With texting becoming the primary means of talking to someone, it only makes sense for you to make your move via texting – especially if the two of you already have a nice dynamic going. But the trouble is finding just what to text a guy so he knows how you feel without scaring him away.

Before we get to what to text a guy when you want to start a conversation, we should first go over some texting ground rules. [Read: How to start a conversation over text with anyone and kick off the flirtiest banter!]

Rules of texting

It might seem like you should just text them whatever you want whenever you want, but there are some unspoken rules of texting a guy that you should know about before diving in for the first move.

Without these guidelines, you could make some mistakes and end things before they even start.

1. Never send multiple unanswered texts

Nothing screams “CLINGY” like sending text after text when he hasn’t even replied yet. We get that you’re eager to talk to him because you like him, but this makes you look desperate. If you want to know what to text a guy to start a conversation, it shouldn’t be a double text – ever. [Read: 12 common texting habits of girls that push guys away]

2. Never text him after 12am

Some people may know of these other unspoken rules, but this one might be new to you. We say you should never text a guy after midnight because most guys take that as a booty call sign – something you most definitely don’t want to be seen as if you’re looking to date him.

Try to keep your texting to normal waking hours. [Read: 18 things you accidentally do that make guys think you’re an easy lay]

3. No sex-talk

You can most definitely be flirty and fun without having to talk about sex with a guy. While you may get his attention with sex, it will be the wrong type of attention overall if you’re looking for something deeper. You can make sexy jokes, but keep it PG-13 for now.

4. When he says he has to go, don’t text him

This is a big mistake that most girls make, and it comes off as super clingy in a guy’s eyes. When he says he has to do something and can’t talk anymore, don’t send him texts while he’s away.

If he has his phone on him, it’ll be really annoying, and if he doesn’t, it’ll be overwhelming when he finally does look at his phone. [Read: 21 clear signs of a clingy girl and how to avoid being one]

5. Don’t let the conversation die

Conversations that go flat quickly never result in a good relationship. Knowing what to text a guy is about consistency.

You want to keep things flowing naturally and never force it. Think of topics to talk about, and if you find something he seems chatty about, stick to it for a while.

What to text a guy to start a conversation with him

Now that you know what to avoid when texting a guy, we can get to the good stuff. You know the how, but here comes the what.

When you want to start a conversation with a guy over text for the very first time, try these text examples and ideas. For sure, striking up a brand new conversation can be nerve-wracking, but at least you’re not face-to-face!

[Read: How to talk to anyone – Master the art of a real conversationalist]

1. Hey there, remember me?

This is a cute and funny way to start a conversation. It will make him smile or it will confuse him but either way, it will cause him to text you back! That’s exactly what you want when starting a conversation.

2. I wanted to say something witty, but my mind went blank

Sometimes, you just have to be honest! Being upfront about the fact that you wanted to text him but couldn’t think of what to say could be all it takes for him to take the heat off you and start the conversation himself!

3. Hey there, how was your day?

We know, many people say that you shouldn’t be predictable when texting someone but everyone likes to be asked how their day went, right?

If you really can’t think of what to text a guy to start a conversation and everything else seems forced to you, just go back to basics. [Read: How to hold a conversation and make people love talking to you]

4. Did you see the game last night? I can’t believe it!

Obviously, this one will only work if there was an actual game the night before and something dramatic happened, but if that is the case, use this example!

5. Think of a shared interest

This one is useful if you already know something that he likes because you can use that as a shared interest. However, only do that if you literally do share that interest otherwise it will come over as fake.

Something like “I went to see the new James Bond film last night, it was amazing!” Hopefully, the conversation will naturally continue from there. [Read: How to text a guy first – 24 ballsy examples that’ll leave him wanting more of you]

6. Let’s settle this – Were Ross and Rachel on a break?

It doesn’t have to be this exact example, but by using a very common pop reference you can connect and start a fun conversation. It’s witty and fun and it’s far away from the usual “hey” text.

7. I enjoyed meeting you and wanted to talk to you again!

It might be borderline flirty but it works! You probably met up with him otherwise you wouldn’t have his number and if you’re messaging him through social media, you’ve obviously met before. Use that meeting as a catalyst towards starting a new conversation through text.

8. Send a funny GIF or meme you’ve seen

Send it and then comment saying “how funny is this?” Remember to make sure it’s nothing offensive however, you don’t know him that well yet!

If you can find a meme or GIF that is related to something you both know, that will work really well. [Read: How to be a fun texter and make them laugh while reading your texts]

9. I was thinking about today and I can’t believe what …. said

Again, you don’t have to text this word for word because it could be that you didn’t have that encounter to talk about, but you can use this as an example and adapt it however you like.

For instance, if you were both in a class together and someone said something funny, remind him of that and start the conversation from there.

What to text a guy to ask him on a date

These examples are ideal for when you’ve already spoken to a guy and you just want to get straight to the date-asking side of things.

1. I’ve got a bottle of wine, a great movie, and no one to keep me company. What are you up to tonight?

This text is perfect if you’re hoping to start a conversation with a guy in person. It’s perfect because you’re not too blunt, but you’re also letting him know that you don’t have company and want some and that you’re ready for a relaxing evening. [Read: How to ask a guy out like a classy girl and leave him wanting more]

2. Have you heard the latest from *your favorite band here*?

Talking about music is an easy way to break into a conversation. You aren’t getting too deep or invested, but people love to share their favorites. This is a great way to get to know someone, but you can have fun banter about your opposing musical tastes. This is especially great if they’re performing in your city, or there’s some kind of show involving their music.

3. What are you up to tonight?

We know this sounds like the world’s most boring text, but it can be a great way to start a conversation with a guy. You text this, and if he answers with something other than nothing much, you will ease your way into more. If not, he may not be interested. And it is best you find that out now.

4. Are you a coffee drinker?

This might just be a yes or no question, but it can carry you into a discussion about your favorite diner, how you take your coffee, and maybe even where you’ll go on your first date. Never underestimate the power of a coffee date! [Read: 14 great reasons why girls should ask guys out directly]

5. What are you binge watching right now?

We are all watching something on some streaming service at the moment. There will be a good conversation here, whether this guy is into sports, dramas, or sci-fi.

You can text a guy about your favorite shows, what you watched growing up, and what new show you’re looking forward to. Maybe you can get together to watch it.

6. You’re a lot of fun through texting, but how much fun are you in person?

Guys are competitive creatures. If you hit him with this text, it’ll seem like that much more of a challenge for him. He’ll definitely want to prove to you that he IS just as fun in person, and you’ll get a date! [Read: 20 witty ways to ask a guy on a date–that he’ll love]

7. You’re really not killing it with the texting banter

If your text conversations with a guy seem to die down quickly, start by putting a little pressure on him. Let him know that he needs to put in the effort too. Texting is a two-way street. If he wants to flirt with you in person, he’ll need to do it over text first. [Read: 40 cute texts to make him smile and miss you more]

8. There really isn’t anyone else that I like talking to this much

This is a really sweet text that will definitely make him smile. Not only will he be flattered, but he’ll also get the hint that you’re into him.

Hopefully, he’ll feel the same way and this text gives him the opportunity he needs to ask you out.

9. Look at my cute animal!

Don’t say it exactly like that but send a cute picture of your pet. Suppose it is funny, even better. People love talking about animals. They will ask you their name, how old, and more. Maybe you can even offer for him to meet your fur baby soon. [Read: 14 reasons why girls should ask men out directly]

10. The party invite

“So, there’s this party I got invited to but I think it’s going to be pretty lame. Do you want to come with me so at least there’s one fun person to hang out with?”

It may seem counterproductive to ask someone to go with you to a “lame” party, however, this really does work. You’re flattering this guy by not only inviting him, but also saying that he’ll be the only fun person at a lame party. It gives him the incentive to go and you’re also revealing how much you like him.

11. What is your ideal date?

Asking about a guy’s dream date via text is great. Are they more into adventures, or do they like to be more casual? This answer can help you plan the first date and let you tell him what kind of dates you like. [Read: The secret guide to attracting men in a way they can’t resist]

12. Why don’t we talk about this over dinner?

If you two are having a really great conversation and you’d rather be in person, just send him this text. As long as he’s not busy and you could be ready pretty quickly, this is a perfect way to go from texting to in-person easily and without too much hassle.

13. You know what, let’s go out sometime

Another very direct approach that doesn’t put too much pressure on a guy. When you’re having a fun conversation with him, just throw this in mid-conversation.

You’re clearly stating that you would like to go out with him, but by avoiding the word “date” you’re making it less formal and easier for him to agree to.

14. Let’s forego the small talk. I like you

If you prefer to be blunt, get right to it. You don’t want to waste your time talking about TV or movies when you really want to ask them out. Be straightforward.

A lot of people prefer that to the slow burn. And if they like you back, this could really be the perfect thing to text a guy to start a conversation. [Read: How to make small talk without feeling awkward]

15. I’ve had a boring day, surely yours was more exciting?

This is a great way to start a conversation with a guy over text because it’s so open-ended and will surely lead to a longer conversation. If you want to go for the big date question, you can then say something along the lines of “well, my day would be better if we could meet up for a coffee.”

Date or general conversation, it’s easier than you think!

Whether you’re texting a guy to straight-up ask him out on a date or you just want to start a basic conversation, these tips will see you through.

It’s probably best to start a general conversation and feel your way into asking him out. That way you can work out whether you actually like him or not. If you already know him a little, then go ahead and get straight into it, but otherwise, remember that he might not turn out to be all that!

[Read: How to flirt with a guy over text – Every little secret you NEED to know!]

Knowing what to text a guy to start a conversation can be difficult, but you just need to know where you want things to go. That first text will guide you there.