How to Text Your Crush Without Being Boring

How to Text Your Crush Without Being Boring

22 Min Read

Texting your crush is both exciting and nerve-wracking.

You’re sitting there staring at your phone, thinking about what to say, trying to strike the perfect balance between being engaging, funny, and, well, not boring. After all, you don’t want your texts to fall flat or, worse, for her to leave you on read. It’s easy to feel the pressure, especially if you’re not a texting pro or if you’re just starting to get to know someone.

But don’t worry – texting your crush doesn’t have to be a stressful experience. In fact, if you do it right, it’s a fun way to build attraction, keep the conversation flowing, and even set the stage for your next in-person hangout (and possibly a hook up).

The key is knowing how to text in a way that keeps things playful and light, interesting, and just a little bit flirty without coming across as too intense or, worse, dull and needy.

So, if you’re wondering how to text your crush without being boring, I’ve got you covered. I’ll walk you through some practical strategies to keep your text game strong and your crush eagerly awaiting your next message.

Tips For Texting Your Crush The Right Way

Now, I know I’ve been telling people that texting is not my strongest area when it comes to dating and seduction. But I still know a thing or two about text game and how to get someone interested in chatting with you and then meeting up.

After all, I’ve been on several thousand dates (yes, THOUSAND) and to set those up, I’ve had more phone calls and text messages than I can count. So you learn a thing or two about how to keep someone’s attention, grab their interest, and entice them to meet up with you for a great first date.

In fact, some of the time I didn’t even have to meet up girls for a date and would occasionally make them excited and horny over text. After which I invited them to come to my place to hook up. So you can even get laid by texting a girl and skip the date altogether, if you’re good enough.

In any case, let’s start with the basics:

1. Start with a Strong Opener

First impressions matter – even over text.

The way you start a conversation sets the tone for the rest of your exchange, so you want to make sure your opener is engaging, fun, and a little more creative than the standard “Hey” or “What’s up?” that women hear two hundred times a day.

Now, while there’s nothing wrong with a casual greeting, starting with something a bit more personalized or unique will instantly make you stand out from the dozens of other messages she might be getting.

Here are a few ideas for strong openers:

  • Reference a shared experience: Did you recently talk about a TV show, movie, or event? Reference it! Something like, “Did you catch the new episode of [TV Show] last night? Mind-blown!” shows that you’re paying attention to the things you both care about.
  • Ask for their opinion: People love sharing their thoughts, so give your crush the opportunity to do just that. For example, “Hey I got a question – what’s your take on pineapple on pizza? I’m having a debate with a friend!” This opens the door to a lighthearted conversation.
  • Start with humor: If you’re confident in your humor, try a playful opener like, “Hey, if we stuck on a deserted island right now, how long would it take you to go insane from my singing?” Or better yet, use some CALLBACK HUMOR if you had a previous interaction where you laughed about something together.

By using a strong opener, you’re immediately showing that you’re not just throwing out a boring “Hi,” and that you’re genuinely interested in keeping things fun and engaging.

2. Be Playful and Use Humor

One of the easiest ways to make sure your texts are far from boring is by injecting some humor into your conversation. Playfulness and light teasing are my go-to strategies and they go a long way in building strong attraction and keeping the vibe fun.

No one wants to be stuck in a conversation that feels more like a job interview than a flirty exchange.

Use Playful Teasing

I’m serious when I tell this time and time again – teasing is one of my secret weapons and probably the thing that I use the most to build MASSIVE attraction with women.

In general, a little teasing is a great way to flirt and keep the conversation lively. But if you master it, you’ll have a very easy way to engage women emotionally. And as I always say – emotions are the main currency of attraction.

For example, if they mention something about their day, you could respond with something playful like, “Oh, so you’re one of those people who drinks iced coffee even in the winter, huh? Bold move!”

Teasing, when done right, shows confidence and keeps the conversation from becoming too serious too quickly. It also shows you’re not afraid to ruffle the girl’s feathers, aren’t needy or desperate to please her and many other great things about you.

Send Funny Memes or GIFs

Memes and GIFs are another excellent way to break the ice and keep the conversation light.

If you see something that reminds you of your crush or is relevant to something you’ve talked about, don’t hesitate to send it. It’s a fun way to keep the conversation going without having to think of a full-blown text response.

3. Ask Open-Ended Questions

If you’re constantly getting one-word replies like “Cool” or “Haha,” it might be because you’re not giving your crush much to work with.

One of the best ways to keep the conversation flowing is by asking open-ended questions. Ones that require more than a simple yes or no answer. This encourages your crush to share more about themselves and gives you plenty of opportunities to keep the conversation going.

I talk a lot about this in my article on how to never run out of things to say to women.

For example:

  • Instead of “Did you have a good weekend?”, try asking, “What did you get up to this weekend? Anything exciting?”
  • Instead of “Do you like music?”, ask “What’s your favorite music to listen to when you’re working out/relaxing?”

Open-ended questions invite more detailed responses, which gives you a chance to learn more about your crush and keeps the conversation engaging and less boring. Plus, it shows you’re genuinely interested in getting to know her better, which will build attraction over time.

4. Keep the Conversation Balanced

One of the biggest texting mistakes people make is dominating the conversation.

Seriously, nobody enjoys a text exchange where they feel like they’re just sitting through a monologue. So if your texts are all about you – what you’re doing, what you like, what you’re into – it’ll quickly make the conversation feel one-sided and, well, boring.

Instead, aim for your conversation to be a balanced back-and-forth interaction.

If you share something about your day, follow up by asking your crush about theirs. If they tell you about something they love, respond with enthusiasm and share something you’re passionate about. The key here is reciprocity. Because when both sides are equally engaged, it creates a much more interesting and dynamic conversation.

5. Don’t Be Afraid to Flirt

Texting is a great medium for flirting because it gives you the time and space to think about your responses. You can be a little bolder than you might be in person, and subtle flirting over text can keep your crush interested without making things too intense.

Use Compliments Wisely

Compliments are a great way to flirt, but they should feel genuine and not over-the-top. For example, instead of sending a generic “You’re so beautiful,” try something a little more personal, like, “I still can’t get over how amazing your smile was the other day.”

This kind of compliment feels more thoughtful and sincere. Compliments that focus on specific details (their personality, style, sense of humor) tend to feel more meaningful and leave a lasting impression.

Make sure to learn how to tell a girl she’s beautiful the right way first though. Because there’s a right and a wrong way to give compliments, and you definitely don’t want to do it the wrong way.

Playful Challenges or Dares

Another way to flirt is by introducing playful challenges or dares into your conversation. Something like, “Bet you can’t guess my favorite pizza topping,” or “I dare you to send me a funny selfie” can add a fun and flirtatious dynamic to your conversation. It also invites some back-and-forth, keeping things engaging and lighthearted.

6. Avoid Texting Like an Interview

A common mistake guys make is turning the conversation into a Q&A session.

Yes, asking questions is important, but if you’re constantly asking one question after another, the whole interaction will start to feel like an interview, which is boring. Plus, no one wants to feel like they’re being interrogated!

So instead of just asking questions, mix in some statements about your own experiences or thoughts. For example, after asking about their weekend, share something fun or interesting that happened during yours. Because once again, when you do this. it makes the conversation feel more natural and balanced.

Here’s how to shift from interview mode to conversation mode:

  • Instead of “What did you do today?”, say “I spent my morning at this new coffee shop that just opened. It was so cool! Have you heard of it?”
  • Instead of “Do you like hiking?”, say “I’m thinking about going hiking this weekend. Do you enjoy hiking?”

By mixing in your own experiences, you make the conversation more dynamic and less of an interrogation.

7. Don’t Overthink Your Texts

Overthinking your texts is a fast way to kill your confidence and make you sound robotic.

Yes, you want to be engaging and interesting, but if you’re spending too much time crafting the “perfect” text, you’ll come off as stiff and unnatural.

It’s VERY important to keep your texts relaxed and in the moment. So don’t worry about crafting a flawless message every time. Because sometimes, it’s better to just let your personality shine through, even if that means sending a message that’s a little goofy or imperfect.

Plus, it shows you’re not overly invested in the outcome and that you’re just shooting the shit, having fun.

This means you can and should just let your texts fly without much filtering. Without over-correcting your grammar. And without even using proper punctuation.

I often send texts like “hey whhat u doing lets go get coffee” or some dumb things like that and it works REALLY well. Because it shows you don’t give a shit about impressing the girl.

I use “lols” and “wtfs” and similar phrases liberally – so don’t think you have to be on your best behavior.

The point is to HAVE FUN WITH WOMEN if you want them to like you. And you can easily do that through text.

Also, if you’re finding yourself stuck, keep it simple. Something as casual as “hey just saw this and thought of you” with a funny meme or interesting article attached can work wonders for keeping the conversation going without putting too much pressure on yourself.

Point is – no one gives a shit if the message is finely crafted. Just shoot the shit with her and have fun.

8. Leave Room for Mystery

One of the biggest mistakes guys make when texting their crush is overloading them with information.

You don’t need to tell them every detail about your day or respond immediately to every text. Part of what keeps a conversation exciting is a little mystery and anticipation.

I’m serious about this – anticipation and suspense are two REALLY great tools to learn and use when talking to women, both in real life and when texting. I might write an article later about how to use them properly.

Don’t Always Be Available

You don’t have to respond to every text the second it comes in. Sometimes, taking a bit of time before responding adds an element of anticipation and makes your crush wonder what you’re up to. Of course, you don’t want to play games or wait too long, but giving the conversation a bit of breathing room can make it feel more natural.

End the Conversation on a High Note

Finally, another great way to leave room for mystery is by ending the conversation before it gets stale. If the chat’s been going well and you’ve had some laughs, you can wrap things up by saying something like, “I’ve gotta run, but let’s pick this up later – this was fun!”

Leaving on a high note keeps them wanting more and sets the stage for future conversations. It also makes them start MISSING you. And when that happens, they’ll start thinking about you when you’re not available to chat.

Two Big Mistakes To Avoid When Texting Your Crush

Now let’s talk a bit about some of the biggest mistakes men make when texting women, especially ones they have a crush on.

If you avoid the following things, your text conversations will become MUCH better.

Texting Too Much Or Way Too Often

Don’t text your crush constantly because it will come off as clingy and kill any mystery you might have created about you.

When you text way too much, it basically shows you have nothing better to do with yourself and your time. Especially if you keep responding IMMEDIATELY to her every single time.

This is bad because her interest in you will wane if she sees you’re always available and don’t have anything else to do but wait for her text and reply right away.

This also includes the clingy and cringy daily Good Morning and Good Night texts. Sure, some guys may think they’re being cute and sweet when they do this. And yeah, the first few times you do it is probably okay. But these kinds of texts get way too boring, predictable and annoying really quickly. And the WORST thing you can do is become someone who’s very boring and predictable. Especially during texts.

This means you should also stop it with the constant “Hey, what’s up?” and “So how’s your day going?” and “Want to meet up?” texts. Because they offer no intrigue, no suspense and just make your messages dull, routine-like and anything but exciting.

Finally, don’t double and triple text before she replies, or she’ll think you’re desperate and needy.

Being Too Logical

Another massive mistake guys make when texting girls is becoming way too logical. Especially if you bombard them with logical questions.

That’s because girls want to connect with you emotionally and to HAVE FUN WITH YOU. And if you’re being all logical and dull, it’s not going to be a fun experience for them.

Sure, it’s okay to ask some logical questions to get the conversation going. But it’s IMPERATIVE to transition as quickly as possible to something more flirty, playful, lighthearted.

Incidentally, teasing and role-playing are great ways to affect girls emotionally, and not just over text but in person as well.

Other than that, push/pull is always a great thing to do, to make your conversations more emotionally charged. So don’t be afraid to take some risks in conversations, as women like men who are bold. (But not brazen, crazy or obnoxious!)

So remember, if you want to have a great time with women, both in person and during text, you should always focus on having fun. And leave logical/dull/boring conversations out the door.

So when you’re texting your crush and she asks you, for example, “So what do you usually do during your days?” Instead of texting her something like “Oh I go to school, hit the gym, hang out with friends, maybe go shopping” or something equally boring, uninspired, dull and something she’ll hear from hundreds of other guys. Text her something like “I travel around the country collecting whiskers from cute and cuddly cats so I can later handcraft them into make-up brushes to secretly sell to girls who are allergic to cats :D” or something equally ridiculous, zany and out of the blue. And then just watch how that inspires a wild and unpredictable conversation.

The point isn’t to be edgy or to say random stupid and ridiculous shit. The point is to have fun, joke around, say something that’s GENUINELY AMUSING TO YOU. And you’ll be unpredictable, memorable, fun and DIFFERENT when you do stuff like that.

Final Thoughts

Again, texting your crush doesn’t have to be a source of stress.

By using the tips above – starting with a strong opener, being playful, asking open-ended questions, and knowing how to flirt without overdoing it – you’ll keep your texts engaging and fun.

Remember, the key to texting your crush without being boring is to stay relaxed, keep it light, and let your personality and humor shine through. And when you learn to mix that up with some flirting and creating sexual tension, you’ll go really far.

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