How to Flirt Over Text Without Being Creepy

There’s both good and bad that comes with flirting over text (and sometimes the downright ugly too!). With dating apps now a staple part of our daily lives, it’s often the first way you start communicating with a potential partner. Because there are still loads of questions concerning how to flirt over text, especially how to avoid coming across creepy, we’re going back to basics and demystifying this classic conundrum.

On the positives first, there’s simply less pressure via text. You’re not standing in front of someone worrying about face-to-face rejection. Yes, you’re hoping to get a response, but there are other things you can focus on aside from your phone. There’s less strain to hold up a conversation and, if you’re worried about a specific text, you can even ask a friend to review it before you press that scary send button.

But on the flip side, and somewhat ironically, you’re not standing in front of someone. It can be hard to make a deep connection when you can’t look someone in the eye. You can’t read their expressions and body language, so you can’t know 100% if someone is into the conversation or not. If you were standing face to face with someone and they looked bored, you’d know and you could walk away.

Flirting over text is, in a lot of ways, similar to flirting with someone at the bar. You should wait to approach someone until they seem to be interested in you and, if they aren’t, you should leave them be. You should try to start a conversation instead of dropping some cheesy, or even creepy, pick-up line on them. Get to know them and spend time learning about them instead.

So without further ado, here’s how to flirt over text the right way, instead of scaring off a potential date. Trust us, it’s not as hard as you might think!

  • Do: Open the conversation in a direct but not over the top way
  • Don’t: Open the conversation with a “hey” or a pick-up line

If you start a conversation with “hey”, here’s how it’s going to go: “Hey.” “Hey.” “What’s up?” “Not much, you?” “Not much.” See how that conversation went nowhere? But unfortunately, that’s how a lot of conversations over text open up. If you’re trying to figure out how to flirt over text, this is a quintessential way not to do it. No one wants to text when they don’t have to text anymore.

Similarly to how you wouldn’t call someone on the phone unless you had something to say, you should follow the same guidelines for texting. Opening up your phone to see “hey” is not going to convince someone that you have something worthwhile to share with them. 

The same thing goes for a pick-up line. Although we typically associate men with being the ones who use pick-up lines, it turns out that both men and women really hate receiving them. The best way to open up a texting conversation is actually different for either gender. 

Women tend to prefer more friendly opening lines, like asking them about their interests which can help start a conversation about mutual interests. Men tend to like more direct approaches, like when they are told upfront that someone’s interested in them. 

This isn’t to say that you should text, “You’re so hot” as an opening line. It’s more to say that you should text, “Hey, I can’t stop thinking about that cute guy I met at the bar.” It’s upfront to show that you’re interested, but it’s also a bit of a tease. Guys like it when a girl is direct and confident, but there’s something to be said for a chase too.

  • Do: Offer a compliment
  • Don’t: Go overboard or gross

According to flirting expert Rachel Dealto, a big part of flirting is really making the other person feel good about themselves. No one wants to go out with someone who either makes them feel bad or who  constantly talks about themself.

That’s why paying a few compliments is an important part of how to flirt over text. Just be careful about the kind of compliments you pay. It’s nice to pay a couple of physical compliments, but if that’s the only thing you’re saying, you’re going to convince the other person that you’re only interested in them because of their appearance. 

When you do pay a compliment on someone’s physical appearance, keep it above the neck. Saying, “Your eyes are beautiful” is a lovely sentiment, if a bit cliché. “Your lips are beautiful” is a little sensual but not over the top. Saying, “Your butt is beautiful” is not quite so pretty. Other compliments, like “Your hands are lovely” are neither lovely nor gross, but they do sound pretty weird and are best avoided.

  • Do: Ask questions
  • Don’t: Avoid their questions

It’s great to show that you care about what your potential partner has to say and about what their life is like. Showing an interest in their interests is similar to complimenting them because it makes them feel good and appreciated. That being said, you should also offer up some information about you too. 

It’s a tough line to tread. On the one hand you’re annoying if you talk too much about yourself. On the other, you’re a little creepy for not offering up any information about yourself. There’s something to be said for having an air of mystery about you, but if you’re avoiding all their questions, they’re going to think you have a potentially bad reason for doing so. 

When you ask a question about them, try to ask things that can uncover mutual interests. Maybe ask them about a particular type of music. They’ll share their thoughts on it and then, when they’re done, you can share yours. You may uncover a band you both like and then you can share your favorite songs by that band. In this way, you’re not offering up a bunch of facts about yourself that have nothing to do with what they say. Instead, you’re both offering up stories that intertwine and show a connection.

  • Do: Keep it light
  • Don’t: Ask about their future relationship plans

While you’d like to know if they’re on the same page as you as far as what you’re looking for in a relationship, it’s best not to have that kind of conversation over text, especially not when you’ve just started to get to know each other.

Questions like “Do you want kids?” are better left to face to face conversations and also shouldn’t happen very early in a relationship. You wouldn’t ask something like that on a first date so it shouldn’t be asked when you’re first starting to text each other either. 

Don’t offer that information up on your own either. It can easily scare someone off if you’re talking about something so far in the future like that when you just met someone. Maybe that person will be the person you have kids with one day, but that day is way in the future and, right now, you just want to spend time getting to know them.

When thinking about how to flirt over text, the best thing to do is think about whether or not you would flirt with this person face to face in the same way. If you wouldn’t say it face to face, you probably shouldn’t text it either. And, if you’re unsure if you’re about to send a weird text, there’s nothing wrong with getting a second opinion from a friend. Good luck and have fun!