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According to a 2024 study by Stanford Communication Lab, 78% of romantic connections that begin through digital messaging fail to convert to in-person meetings — largely due to poor text conversation skills. Yet the same research shows that individuals who master strategic texting techniques are 3.2x more likely to secure successful dates and maintain long-term romantic interest.

Gentlemen! So you want to know how to make someone like you over text, eh?

You’ve come to the right place.

I’m going to share with you some of my top tips for crafting the perfect text message that will have them crushing on you in no time.

But before we get started, let’s take a moment to acknowledge the fact that this whole process can feel daunting. I mean, how are we supposed to present ourselves in a way that’s both genuine and appealing through mere words on a screen?

Don’t worry, I promise it’s not as hard as it seems. With these proven tips, you’ll be winning them over in no time.

At its core, getting someone to like you over text messages is an extension of the banter lessons we teach at The Art of Charm.

The Key to Effortless Flirting Over Text

Whether you’re texting someone you just met or someone you’ve known for a while, the most important piece of advice is to have fun.

Keep your texts playful and lighthearted. Make someone smile and light up when they see your message and you are on your way to getting them to like you over text. (Related: texting someone you just met)

Flirting over text is like a modern dance of wit and charm, played out in digital letters. The key lies in striking a balance between playful teasing and genuine interest, all while keeping it light and fun.

It’s about hinting at your interest without coming on too strong. For instance, instead of just asking how their day was, add a twist with something like, “Bet my day was crazier than yours! Care to compare notes?” It’s playful, prompts a response, and opens the door to deeper conversations.

Again, this is about being playful. Let’s say you challenge her to a “whose day was crazier” competition. You don’t have to talk about your actual day. (Related: playful banter examples)

Say something about how you were on the verge of curing cancer when a dinosaur smashed through the lab speaking Spanish and looking for the bathroom. Playful and lighthearted.

The beauty of text flirting lies in its subtlety and timing. Timing is crucial — knowing when to send that witty reply or a cheeky emoji can turn an ordinary conversation into an intriguing exchange.

And remember, the best flirting often happens between the lines. It’s in the way you playfully challenge their opinions, share amusing anecdotes, or casually mention an activity you could do together. Just don’t make these common mistakes.

But how will you know if someone likes you or they’re just playing games?