How to flirt with a guy over text without being obvious

You really like him, and you want to show it. And you want to get the ball rolling, because you think he might like you to. Or you’re willing to do just enough to find out if he might. You are not, however, willing to show all your cards and set yourself up for rejection.

How do you flirt over text without being obvious? It’s all in keeping balance! You want it to be clear enough that you’re flirting that he knows to flirt back. You just don’t want to be TOO obvious. But why? By being too obvious, you:

  • Risk turning him off—most guys like to feel like they’re the ones initiating
  • Risk developing a reputation…you want to flirt so he will like you, not use you
  • Risk rejection, in case he figures out you’re flirting and tells you, “No thanks”

Okay, so those all sound pretty bad. How do you flirt over text “just right” to avoid under or over-bidding your cards? And how do you do it through text?

  1. Text him just enough to make it clear he’s on your mind! If you text too much, you can risk coming on too strong or—worse yet—it ca be annoying! “Good morning” and “good night” texts might be a little much. Aim to be the one initiating the texts roughly half of the time.


  1. Ask him questions about himself. Yes, you want to impress him, but all that stuff you normally like to tell people about yourself can wait. And so can at least half of your more self-serving stories. Women are so spoiled, we’ve grown use to everyone asking us questions so we can monologue about our own likes, experiences, and personal bragging rights. If you really do like this guy, you should want to get to know him, too! Ask questions about stuff you’d really like to hear him talk about!


  1. Instead of peppering in compliments, slip matter-of-fact statements in like it’s OBVIOUS how awesome he is. Assume he already knows how smart or handsome or funny he is, because it still communicates the compliment, and doubles in value with the assumption that he’s so awesome he should know it! It’s also less obvious that you’re complimenting him.


Example: “Of COURSE when you spoke at the wedding reception all the girls liked hearing you talk about love and commitment. ☺”

DON’T USE: “But you’re so cute, I bet all the girls were thinking about you when you spoke at the wedding.” Just tell him what the other girls were thinking!

  1. If he starts to join in and flirt back with you, feel free to “up the ante.” You can start to use more aggressive tactics like light teasing, but be careful that it’s just a little! For example, give soft, playful yeses instead of hard-to-get nos.

For example, if he starts to joke that you two should really get a cup of coffee to graduate from text chat, say “Yeah, that sounds about right” instead of “Ooh, I dunno…” Make it a yes plus a joke, not a no with a bait.


So, between flirting over text and in person, what’s the big difference? First, you have an advantage in texts that you can’t beat in person! By flirting over text, you can read and re-read your message before you polish it and send it off. Also, you can throw in a “dramatic pause” between messages a time or two for added effect. Just don’t do it too often and let him think you’re busy doing something else.

In other words, flirting over text gives you more control over how and when your message is delivered.

The other big difference in flirting over text are emojis! And oh boy, what fun they are! After a good, flirty conversation, you’ll probably see a lot of cute emojis winking up in your “recently used” tab on your telephone. But be careful, because each emoji packs a lot of punch.

Emoji advice: Be sure to think through the emojis you use, and to not overuse any. Avoid hearts and smoochie faces if you’re serious about flirting WITHOUT being obvious. Throw in an occasional wink, but otherwise stick to grins and smilies. You can use the smoochies once you start flirting more aggressively, but if you’re still in the “subtle” phase, take care to do it right!

Most importantly, be ready to roll with the punches with flirting over text! If he starts to pick up on things and flirt back, you have nothing to be afraid of. Start throwing in those smoochie emojis and all the compliments you care to give him! And, finally, you can start talking a little more about yourself and feeding him some stories he might like.

And the million-dollar secret? You don’t ever want to make it too obvious that you’re flirting before he takes the bait, because men thrive on feeling like they’ve made the first move.