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80 Tips, Rules & Examples to Text a Guy First & Start a Fun Text Conversation

You want to know how to text a guy first, but you’re worried about rejection or making the wrong move. Never fear! We have all the tips you need. 

how to text a guy first

Sometimes you’ve gotta make life happen, no matter how terrifying it might seem. If you have your eye on a sexy guy, you need to go for it and learn how to text a guy first. If you wait around for him to make the first move, you might get impatient waiting.

And honestly, there’s nothing wrong with texting a guy first. No, it doesn’t make you desperate or needy.

In fact, it makes you seem like a confident and ballsy woman – and those traits are always admirable. You have his number, Facebook, or Insta account, but nothing is happening. He’s not texting you, and you’re not texting him. Well, how do you expect things to progress if something doesn’t happen?

It’s time to take action and learn how to start a text conversation with a guy, especially if he’s not making a move. *for wherever reason – maybe he’s shy!*

Even if nothing ends up working out, that’s okay. The point is you decided not to wait around for him to make a move, nor did you waste any time playing silly games.

Why should you text a guy first?

When you know how to text a guy first, then you’re taking things into your own hands. You’re not waiting for a guy to make the first move, which could take forever. Some guys are incredibly awkward and shy, so it’s almost an impossible situation to wait for them to start texting.

Knowing how to start a text conversation with a guy is a great dating skill as it lifts the burden off the guy. Of course, you should also know when he’s not interested in you, but hey, you made the first move – that’s a start!

There’s also something admirable about a woman who had the guts to text a guy first, regardless of what anybody else might think. It makes you appear certain, confident, and totally in control.

It’s like you sitting in the driver’s seat, and asking him “so are you in or are you out? I don’t have time to waste!” How badass is that?! [Read: How to text a guy – 18 secrets to go from timid to text temptress]

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. 

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 before you let your mind wander further. 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]

Make peace with being the instigator

It might be that you’re not entirely comfortable with being the one who makes the first move, but it’s something you should embrace and make peace with. It’s likely that for the first few texts at least, you’re going to be steering the conversation. [Read: What to text a guy when you’re making the first move]

You’re asking questions and trying to think of the next thing to say. That’s fine and totally normal. Remember, the guy is probably feeling a little nervous and not sure what to say too!

This is where having a plan and knowing how to start a text conversation with a guy also helps. While we’re not trying to turn this into a brainstorming project, it doesn’t hurt to think about things before you text and come up with a few interesting things to say.

Remember, there is going to be a natural lull in the conversation, because life happens and maybe dinner is ready, or your guy needs to go out. It’s fine, and it will restart if he’s interested. He gave you his number, so that’s a good sign!

Look for clues in his messages and try and ascertain how he feels about the conversation. If you’re not feeling it, it’s fine to back off a little. Guys are guys, and that means he’s going to wonder why you’ve slowed down and want to know where you are!

When learning how to start a text conversation with a guy, you need to be brave and just go for it! [Read: Dating anxiety – what it is, 39 causes of panic, and signs and steps to get over it]

How to text a guy first and leave a great impression

Men are used to initiating everything, but that doesn’t mean it isn’t helpful to know how to text a guy first. There are many scenarios where a guy can end up impressed when you contact him first. Whether it’s a friend, a stranger, or a co-worker, you can always text a guy first without appearing weird or needy.

So if you want to text a guy first and play it cool at the same time, here’s everything you need to learn how to start a text conversation with a guy.

1. Say something other than “hi”

It doesn’t take a lot of common sense for this to be obvious. Saying “hi” is fine, but there needs to be more.

Bring up something that happened at school or work, mention a meme or video clip you saw, or ask him how he is. Texting him ‘hi’ and nothing more, is the last thing you should do when figuring out how to text a guy first. [Read: 25 very cute and fun ways to say “hi” in a text message without using the word “hi”]

2. What’s your goal of texting him?

Keep your goals in mind when texting him. If you want to hang out with him, make sure your text conversation will eventually lead to that. It’s no good learning how to start a text conversation with a guy if you don’t know what you want to come of it.

The goal of texting him should be the entire foundation of your texting relationship. If you want to land a date with him, everything you say should work toward that goal. [Read: The common texting habits of girls that push guys away]

3. Don’t text him late at night

We know it’s really fun texting at night as you tend to get more personal with one another. However, it also leads to booty-calls, which is a big no.

If you want something serious, don’t text him after nine pm. Anything later than that, you’ll give him the impression that you want something else. [Read: How to read mixed signals from a guy and interpret his real intentions]

4. Wait for him to reply

Don’t send him another text right after you send him one. Give him time to reply. This is something girls tend to do, and frankly, it’s going to ruin your chances with this guy. *if your goal is to land a date, that is.*

You need to give him time to reply and not take his silence as a confirmation to spam him with more texts. What if he didn’t receive your messages? He probably did. What if he didn’t like what you said? Don’t overthink it too much.

Just wait for a while and give him the time to respond. He will!

5. Ask him questions

If you want to get to know him, ask him questions. Now, this isn’t a job interview, so you don’t need to grill him. Don’t ask him intense questions too early on either, but stay with light but interesting topics.

Questions are always a fun way to get to know him so ask away! [Read: 110+ sexy and dirty questions to ask a guy and subtly seduce him]

6. If he ends the conversation, don’t text him

If the conversation ends, you don’t need to restart the conversation an hour later. When you’re figuring out how to text a guy first, remember to give some space for things to develop.

Smothering him or making him feel suffocated won’t grab his attention, but it’ll push him away altogether. [Read: Why did he stop texting me? 13 rules you MUST follow]

7. Don’t be glued to your phone

When he texts you, don’t reply right away. It’s okay to give it a few minutes *or even an hour or two if you’re texting back and forth all day* until you respond. In fact, this makes you seem like you have an interesting life.

Nobody wants to text with someone who’s not interesting, so don’t be afraid that you’ll lose him by texting back a second later. Everyone is busy and has things going on in their lives, and he knows that. So, reply when you have time.

8. Let the conversation end naturally

We know you like him, but if you feel the conversation is ending, don’t try to hang on to it. The worst thing is when you see someone is trying to keep the conversation alive, when it’s dead already.

The more you force the conversation to keep going, the uglier it gets. [Read: How not to be a dry texter – The signs you’re one and the quick fixes]

9. Stay away from sex-talk

Learning how to start a text conversation with a guy also means knowing what to avoid. If you’re only looking for a casual fling, you can eventually slide into some sexual topics.

But, if you want something serious with him, then avoid talking about sex right away.

This is a big no, especially if your goal is to land a date with that guy you like! There’s more to you than what’s between your legs and for now, he doesn’t need to know.  [Read: How to flirt with a guy over text – Everything you need to know] 

10. Spell properly

Listen, we don’t care how old you are; you need to spell properly. There’s no need for you to write, “brb,” “u2,” “sup” – come on. This is a huge turn-off in texting, no matter what gender you are.

It’s basic texting 101; you should know this by now.

11. Let him text you afterward

If you made a move and texted him first, from now on, you don’t necessarily need to be the one who always makes the first move. Let him text you first a few times as well.

This is a good test to know if he likes you as much as you like him. Is there mutual effort in the conversation? Is he initiating conversations as well?

If he doesn’t text you unless you text him, maybe he’s not as interested in you as you think. [Read: What it means when he never texts you first but always replies]

12. Show your personality

If you want to develop a connection, show your personality in your texts. This is one of the most important things to remember if you want to know how to text a guy first.

In a text conversation, a guy falls for your personality since he gets a glimpse of who you are. If you have a great sense of humor, don’t be afraid to crack jokes and make him laugh.

13. Keep the text short and sweet

No one enjoys reading an essay-length text message. You have to keep your text short *a few lines long unless there really is something important to say*, or you’ll automatically bore him to death.

Make it short, concise, and direct to the point. If it has to be longer, then send a voice message or better yet, call him. Your texts should be short and sweet. There’s no need to write a novel. [Read: What to text a guy that will get his attention – 25 texts that work like magic]

14. Don’t ask yes or no questions

When thinking of the right questions to ask him, make it as broad as possible. Keep it vague if you must, but avoid questions like “had breakfast?” or “are you at work?”

Make sure you’re asking questions that won’t result in one-word answers because you’re not getting the best conversation with those questions.

15. Use your humor

If you want to know how to text a guy first, use your humor to your advantage. Text him a cheesy pick-up line, use gifs and memes, or say something that sticks in his mind.

This is the best way to grab his attention and ensure that he picks up his phone to text you back immediately because he has so much fun every time you both have a conversation over text! [Read: How to be a fun texter & make them laugh while reading your texts]

16. Find common ground

If you want to develop a connection with this guy over text, find something in common. Maybe you both like the same shows, or maybe they share your passion for music.

Whatever it is, if you want to know how to start a text conversation with a guy, find something you can both talk about for hours and never get bored. It’ll keep him engaged and interested enough to keep texting with you!

17. Talk about your pet

Everyone *unless you’re an unusual human being*, loves talking about their pets. If you’re a pet owner, you can send him a photo of your dog over a text or even talk about it with him. If he also has a pet, even better!

You can share your love for your pets with one another, and it’ll be the cutest conversation ever. [Read: Do couples always have to like the same things?]

18. Use emojis but don’t overuse them

Emojis are a lot of fun, and they’re perfect to add feeling to your words. And they’re also great to use because you don’t seem extremely cold to the guy you’re texting. But if you want to know how to text a guy first, remember not to overuse emojis.

There are only so many smiles and emojis you can use, before he sees you as an immature person who only talks in emojis!

Of course, emojis are perfect for flirting, but don’t use tons of emojis in every sentence – one or two is enough. [Read: 20 flirty emojis that’ll make you a pro flirty texter in no time]

19. Mention something about how you met

If you met in a bar or dating app, make a reference to the setting or maybe his dating profile. It’s a great text conversation starter when learning how to text a guy first.

You can even tease him about how cheesy his dating profile is, and that’d make a great laugh on just the first few texts.

20. Leave him wanting more

If you want to keep him hooked to texting you, then keep the mystery alive. You can’t spill all your darkest secrets and personal details over text.

Leave some for wonder because that element of mystery is what will make him ask you on a date or to hang out with him. If you reveal everything, he won’t feel the need to ask you out. [Read: How to be mysterious without going completely overboard in the role]

21. Don’t keep asking him what he’s doing

The most common repetitive questions in texts are “what’s up?” and “what are you doing?” both of which are very dull starters. You already asked him once, and there’s no need to keep repeating this.

If you don’t have anything else to say, then stop forcing the conversation. Try again in a few hours or days when something interesting is happening.

22. Be mindful of your tone

Texting is open to misinterpretation, so be careful if you’re attempting a joke or sarcastic comment. He could take this seriously and be offended by your text, leaving him to stop texting you entirely.

Always watch your words and tone, especially if you don’t know one another that well yet. This is where an emoji can work wonders to get a point across, but remember to use them in moderation! [Read: Texting your crush – A step-by-step guide to doing it right]

23. Flirt a little

If your goal is to land a date with him, then flirting is important! This adds a little fun to the text conversation, and it gives him clear signs that you like him.

Playful banter is also a way to make a lasting impression on him. Just be sure not to go overboard in your flirting moves that can potentially make him feel off.

24. Take it off text

You’ll know when it’s time to take your conversation off of text messages. And when you get that feeling, it’s time for you to make a move.

Or, better yet, make the guy make the move and ask you to hang out or on a date! [Read: How to get a guy out to ask you out – 15 easy, sneaky, and really fun ways!]

25. 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]

26. 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.

27. Accident-proof your texting habits 

It’s always a good idea to draft your first message on your phone somewhere else, e.g., your notes app, rather than straight into the message. If you want to change it, what if you accidentally press send? There’s no way to get it back!

Drafting in your notes app means you can read it, re-read it, tweak it, and read it again before you paste it into the message box and send it. [Read: How to know when to stop texting a guy]

28. Relax

We know you like this guy, but if you’re freaking out already and you haven’t even sent a text yet, it’s not going to go well. You’ll overthink what you’re saying, and it won’t be the natural YOU speaking. 

So, just take a breath and chill out for a second before talking to him. Sure, he’s cute and all that but he’s just a guy. Repeat to yourself, “He’s just a guy.” [Read: The most common texting habits of girls that push guys away]

29. Remember that conversation is a two-way street

This is the important part when you’re talking to a guy. You need to make sure the conversation is going both ways. If you’re the only one talking, then you need to back off. Don’t be the only one talking.

If you’re asking him questions, but he’s not giving much back, then he may not be interested. If you only talk about yourself and forget to ask him questions, well, you come off self-absorbed.

30. Stick to your style

Don’t try to change the way you text to impress him. Keep to your own personal style and stay true to that. 

But this also means you need to be aware of the way he writes. You may use emojis when you speak which is fine, but if he doesn’t, don’t assume that he’s not interested. Everyone has their own style when it comes to texting. [Read: 20 flirty emojis that’ll make you a pro flirty texter in no time]

31. Throw in a couple of voice messages

Now some people really don’t like them or they’re unable to listen to them because of work. But, overall, voice messages are great. They’re another way to add a personalized touch to your texts. 

Plus, sometimes your thumbs get sore, so, give them a rest by sending a voice message.

32. Stay positive

He isn’t your boyfriend, so you’re still trying to get to know him and see where he stands with you. Keep the conversation in a light tone. 

Of course, if you have a bad day, tell him, but keep the whining and complaining down to a minimum. No one likes sitting through a conversation with someone spewing negativity. [Read: How to be a positive person and find the silver lining]

33. Keep the focus on getting to know him

When it comes to knowing how to start a text conversation with a guy and keep it going, don’t be shy to ask about what his interests are, if he plays sports, what movies he likes, etc. 

This is a good opportunity to filter out the basic information about him and see if you generally are interested in the kind of life he lives. 

Of course, you don’t have to ask him straight up if he likes the same movies, but you can ask him indirectly by commenting on a movie you watched and then see what he says. [Read: 60 deep, fun questions to get to know someone romantically as a match]

34. Do your best to keep the overanalyzing to a minimum

This is going to be hard because we all overanalyze. But seriously, try to keep it down to a minimum. Don’t read over his messages, again and again, trying to see the emotion behind them. Just leave it. 

Listen, if he talks to you, you already know he’s curious, so that’s a good start. [Read: 20 no-fail signs to know for sure if a guy likes you while texting]

35. Don’t be so quick to answer

You don’t have to always answer his messages within seconds of receiving them. Remember that people pay attention to the patterns of others. 

Get him used to you not quickly replying to messages. It gives him the idea that you’re busy and also gives you the time to think about how you reply. [Read: 50 texts to make a guy think of you, miss you and want you more]

What to text a guy to keep him hooked

Now that you know how to start a text conversation with 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?

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

3. Hey there, how was your day? [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!

5. Think of a shared interest [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?

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

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

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

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

12. What are you up to tonight?

13. Are you a coffee drinker? [Read: 14 great reasons why girls should ask guys out directly]

14. What are you binge watching right now?

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

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

17. Look at my cute animal! *and of course, send a picture!*

18. 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?

19. What is your ideal date? [Read: The secret guide to attracting men in a way they can’t resist]

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

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

22. Let’s forego the small talk. I like you [Read: How to make small talk without feeling awkward]

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

24. What are you up to this weekend? [Read: 60 get to know you questions for a new romance]

25. I’ve been so stressed out at work today, any tips on how to de-stress?

26. What’s your star sign?

27. Did you see the news today? What do you think about …. *insert interesting story*

28. What was the highlight of your day?

29. I can’t decide what to make for dinner, any ideas? [Read: Foodie dates: 15 trendy dinner ideas for new couples]

30. How did your *insert something you talked about before* go today? 

31. I’m trying to book a vacation, where do you think I should go?

32. I have a presentation tomorrow, help me calm down please!

33. Let’s settle it – pineapple on pizza; yes or no? [Read: 20 revealing questions to get to know someone better]

34. I saw your Facebook update, your photo looks cool!

35. Have you ever sent an embarrassing text?

36. Have you ever text someone and been really nervous about it? [Read: How not to be nervous for a date and feel super calm instead]

37. What is your favorite song?

38. I need a new Netflix obsession, any recommendations?

39. Describe your perfect day in five words

40. You’ve won the lottery, what will you buy?

41. Help me out – iPhone or Samsung?

42. Adulthood sucks sometimes, what do you miss about being a child? [Read: Relationship facts – The real facts of love no one talks about]

43. What is your favorite smell?

44. Wanna meet up? *just go for it!* [Read: How to ask a guy out like a real classy girl]

When to ask him out

When you have been texting back and forth for a while, and you’re pretty sure there’s a spark, when should you ask him out? Maybe they’ll ask you and you won’t have to think about it! If there is no question coming your way, be the one to do it. 

Go on, be brave! [Read: How to ask a guy out and get the answer you want]

You can do this very casually, “I’ve been going to this really cute coffee shop lately, do you fancy joining me?” Or “There’s a band on next week I really want to see, do you want to come?” If he says yes, fantastic. If he doesn’t respond in the way you want him to, shrug it off and move on.

Seriously, there are plenty more fish in the sea, and nobody has time for an uninterested guy! If the conversation has been going well so far, the chances of him refusing a meet up are extremely slim and should give you the confidence to take your texts to face-to-face meetings. [Read: The no-fail signs the guy you’re texting really likes you too]

You may think learning how to text a guy first is scary, but you will get better at it with each try. This way, you’re taking matters into your own hands and initiating a conversation with him instead of waiting forever for a guy to make the first move.

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Preeti Tewari Serai
Preeti Serai
Preeti, the founder of LovePanky, is an eternal optimist and believer in the beauty of love and life. With an exhaustive experience in love, relationships, and ...