Flirting over text with your potential online matches

When my mom asked me to help her set up an online dating profile, I was surprisingly thrilled! Most people would think it’s a little weird for a son to help his mother with such things, but I wish my mother nothing but happiness in her life and will continue to support her through whatever decisions she makes.

Wouldn’t YOU?!
Thought so…

In the year that she’s been on the apps, it has made one thing abundantly clear: she sucks at online communication. And she’s not alone.

In reviewing a lot of the men who’ve "flirted over text" with her, I’m ready to put some of these “gentlemen” on a list somewhere and report them to the appropriate authorities.

I guess it comes from my years of experience dating online (brag), but I forget that some people—especially older ones—have some trouble being flirty when all they have is a keyboard and Jesus.

So, take it from a pro who’s spanned the full spectrum of experiences you can have out of being vulnerable with strangers on an app and step up your texting game.

Forget subtlety: it doesn’t work

This one’s for all the people who love sarcasm out there, which no one should be because sarcasm is my thing.

But if you’re going to steal my thing, it’s better to let your soon-to-be date know what you mean by putting it in brackets if you don’t want to sound like the absolute idiot that you are (just kidding, I don’t actually think you’re an idiot, I’m just trying to lead by example… see?!).

Once you’ve established a familiar texting rhythm with your partner, you can always pause for dramatic effect… but only if you’ve primed them.

Believe me, there are plenty of guys out there who probably think I’m a self-righteous idiot because I sent a “just kidding!” too late and got blocked

...Carl, if you’re out there, I really am sorry!

👍 To using emojis and gifs when you're flirting over text

This one might be a bit of a controversial one but, for me, using emojis is the way to go! As mentioned in the previous point, subtlety is hard when all you have to rely on is a thin, sans-serif typeface and your weary eyes.

But if you add an emoji – or, if you’re feeling brave, a gif – your texts become more expressive.

I’m not advocating for you to send giant, emoji-laden collage texts to describe your every emotion. But I will not stop you from expressing yourself if that’s your thing.

Particularly if you have a bit of a wry, sarcastic sense of humour, a well-placed eye roll in combination with an upside-down smiley face can help let the potential match you’re texting know you’re joking.

And it lets them know you’re young and fun—just don’t use the cry laughing emoji, apparently that’s very... cheugy (... and apparently that’s uncool in Gen Z speak).

Illustration by Anđela Janković

Stop stressing about the time between messages

I hope the person who perpetuated the myth that ‘texting people right away seems needy’ is sitting at home alone in what I can only assume to be a single room with shag carpet, a jacuzzi, and a waterbed. The gross, out-of-touch, hairy uncle lifestyle they deserve.

And isn't flirting over text with anybody. Ever again.

Truth is: your potential match won’t think you’re too needy for messaging someone back right away. Or in a reasonable time frame. You’re also not going to get any points for making someone sweat it out as they anxiously wait for you to text them back—you might even lose a few.

If you have the time, respond to a message!
If you don’t, don’t!

But communicate that to the other person.

Just because someone hasn’t messaged you in a couple of days, doesn’t mean they’re not still interested in you. They might be going through a busy period at work, or reconnecting with their long-lost sibling, or have accidentally slid their car off a cliff and are waking up from a coma!

You don’t know if the SMS waves from the snarky goodbye text you’re about to send will interfere with their life-support machine, so have a little grace.

Be wary of the length of your messages – because if you make things too long, it’s off-putting and makes you look needy. You don’t want that! You want to keep something short, but not too short, because if you message something like “hi.” you sound like a sociopath! But if you give this person the outline for your memoir, that’s also sociopathic behavior! So, if you're flirting over text, keep it short, but not too short. You know what I mean? Good!

… See how stressful that was to read? Don’t do that.

Don't read too much into things

My mom will sometimes rage unmatch people who don’t re-start a conversation with her after a couple days of silence. She’ll groan about how guys don’t talk to her, and I’ll posit, “well, have you talked to them?”

And then she’ll throw me out of her house (just kidding... well, kind of).

Maybe it’s because I’m a hollow, emotionless husk of a human, but I don’t actually take relationships with people I meet on the internet seriously. Why would I? This person wasn’t in my life a week ago; I don’t owe them anything, and they don’t owe ME anything. Don’t be that person who, after a week of messaging, gets too attached to someone.

Just chill.

Talk to someone else on the app, take a walk, lean your dreary head against a cool wall and contemplate where it all went wrong. If that person you were pining over was mutually worth it, they’ll message you.

If not, you dodged a bullet!

Trust Your Gut!

This is probably one of the most important things when you're flirting over text messages, and it’s something that took me years to figure out: if someone doesn’t like the way I’m messaging them, then we’re probably not going to work out.

People agonize over the perfect message to send back to their potential love match, but it honestly doesn't have to be such an excruciating process. Just text how you normally text people. This person is going to, hopefully, receive a lot of messages from you. If you mess up one or two, it’s a drop in the ocean. My first boyfriend and I talked on-and-off the apps for four months before we hooked up – I mean, went on a PG-13 date.

I know this is a little cliché, but in a relationship, communication is key. There are plenty of people in a 10-mile radius – or 30, depending on how far you’ve set your location radius.

Don’t change the way you message for someone who’s probably a catfish and just try to put your best foot forward… and if you’re the catfish, looking for some tips and you made it all the way here: here’s one: stop asking for people’s credit card numbers… it’s a dead giveaway.

Chris Middleton