Connell Barrett, a dating coach for men, answers your questions about how to flirt over text in detail.
How to Flirt over Text
Hey, Connell. The problem I’m facing is that I’ll get a woman’s number from Tinder or Bumble, but then she’ll go quiet and lose interest as we text. It’s so frustrating to have a good match go nowhere. How do you flirt better over text?
—Harold, 35, New York City
I feel you, Harold. It can really sting to finally get a match with a cool, attractive woman, and then get her phone number… only to have her go quiet!
So close, but yet so far.
To help you stop getting ghosted and start getting more dates, here’s some help.
First, let’s define what flirting is. It’s playfully, charmingly conveying your romantic interest in a light, clear manner—and not in a vulgar way.
The great news is, these days you can text using your words, voice, pics, and emojis. You have more tools than ever to text your way to romance.
Now, many men try to flirt, but they either fawn over their crush (“You’re so beautiful, so amazing”), or they come across as merely friendly, or they just boringly rely on clichés (“How are you? How’s your day?”) Those are all ineffective strategies.
Here are the dos and don’ts of flirting over text.
DO MAKE YOUR INTEREST CLEAR
You want your crush to know that you’re flirting with them, and not to confuse it with mere friendliness. If they don’t know you’re flirting, then it won’t be effective. It’s the difference between writing, “I can’t stop thinking about you,” instead of, “I was just thinking about you.”
Cleverness is a nice bonus, but clarity comes first. When in doubt, just say to someone, “By the way, I’m really liking you” or “Hey, you know what’s attractive about you? The way you…” and then tell them.
DON’T USE BORING OPENERS
Most women are tired of hearing “Hey,” “Hi,” “How’s your day?” as an opener. Avoid lazy clichés. The best openers are personalized, giving them something—say, a joke, a compliment, or a fun question she wants to answer.
So instead of “How’s your day?”, lean toward, “How did you name your dog?” or “Since you’re the wine expert, tell me—what’s your favorite wine bar?”
Clichés kill chemistry. Keep things light and personalized to make sparks fly.
DON’T GET TOO SEXUAL TOO SOON
Early on, keep your text messages G-rated or PG. Getting too sexual too soon can come across as vulgar. Think, “Charm, not smarm.”
DO PLAYFULLY TEASE YOUR CRUSH
Texts that playfully tease can amplify the sparks. Think of the smitten schoolboy who pulls the pigtails of the girl he likes.
The secret? Tease her about small, light topics that she wouldn’t get upset about—like, say, her favorite foods or movies. “What? Your favorite movie EVER is ‘Pirates of the Caribbean’? I was really liking you until you admitted that ;)”
NEVER tease her about potential sore spots such as her weight, looks, or pets. That will backfire. My client once teased a date about her dog’s appearance, comparing it to a rat, and it killed the vibe. Instead, tease about light, surface-level things.
DO USE PHOTOS
If a picture’s worth a thousand words, the right flirty picture is worth a thousand texts.
Sending a good photo—showing off, say, your favorite tattoo, or the amazing outfit you’re wearing—will make a big impact. A woman I dated used to send me selfies, along with a caption—“Here I am, looking like a snack”—and I couldn’t get her out of my mind for the whole night.
DON’T FORGET TO USE EMOJIS
It’s easy to have miscommunications over text. Emojis to the rescue! They can make an otherwise “just friendly” message feel very flirty.
The right emoji adds the light, playful tone you want to a flirty text message.
When in doubt, use the winky-face emoji, the heart-eyes emoji, or the very underrated upside-down smiling emoji.
As a general rule, avoid using more than two emojis per message, so as not to come across as overly eager.
DO USE AUDIO MESSAGES
Don’t settle for only text messages alone. Use your phone, or app’s, audio feature to send vocal notes. Few things are sexier than hearing your crush’s voice, which can dial up the romantic tension.
A couple tips. First, keep your audio notes short—less than 60 seconds. You don’t want to sound like you’re rambling. Less is more.
Also, try to sound as natural and relaxed as possible. To help you loosen up, send a “test” audio message about anything to a good friend, just to get your voice and vibe relaxed. Next, mirror that tone when sending the audio to your crush.
Sending a voice note projects self-confidence—and confidence is sexy as hell.