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How to Flirt over Text

Connell Barrett, a dating coach for men, answers your questions about how to flirt over text, how to approach with confidence, and how to escape the friend zone.

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.


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.


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. 


Early on, keep your text messages G-rated or PG. Getting too sexual too soon can come across as vulgar. Think, “Charm, not smarm.”


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.


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.


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.


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.


OK, this happens all the time—I see that incredible woman who I’d love to approach, and I just can’t go and break the ice with her. It drives me crazy! How do I get over my fear of rejection?

—Gary, 44, Yonkers, NY

You need to apply my Universal Rejection Rule. Think of it as a firewall that protects your mental software from indulging in the fear of rejection.

Before I share it, a quick note: The goal here is not to totally eradicate feeling rejected. You’re human! You’re allowed to be bummed if a girl isn’t into you. But you want to minimize that pain and refocus on achieving your dating goals.

Here’s the Universal Rejection Rule:

“I’ll only feel Rejection if I indulge in the illusion that a woman whom I barely know can reject me, instead of remembering that there are a million more girls, and I have more to give.”

This rule rules. It calls bullshit on “the illusion” that someone who doesn’t know you can “reject” you. And the phrase “instead of remembering” shifts your mind to the abundance of dating options that you do have and the abundance of love that you offer.

Dating sucks for tons of men because of rejection—they see it as a Pandora’s Box of painful emotions. This rule locks the box, reminding you that you have endless options and so much to give.

My client Jeff used to battle approach anxiety. When he started to apply this mantra, he went out on the town and approached more than 20 women in one weekend. He got “rejected” several times, but his new rule helped him brush those off.

He also got a phone full of numbers and made out with a total cutie on the dance floor.

Now, you won’t be instantly confident all of the time—that only comes with reps.

But this new rule creates an opening, giving you a burst of belief and confidence… and that’s enough to start meeting some women, and soon getting phone numbers and dates.


I’m starting to get some really good dates, with all the Tinder tips in your book. But I’m still hearing, “Hey, I’m not feeling it” too often after first dates. It’s getting frustrating. How can I smash out of the friend zone on first dates?

—Tommy, 29, Boulder City, Colo.

Ahh, the Friend Zone. I didn’t just live there, back in the day. I owned vast tracts of real estate there. I was a Friend Zone oligarch.

In my book “Dating Sucks but You Don’t,” I share over 100 tips about escaping the Friend Zone on dates. Here are five of my favorite.


1: Show Clear Interest


If you’re interested in a woman, make it clear. It can be as simple as saying, “Let’s go on a second date,” rather than making it a mystery. On the date, don’t hide your feelings. Tell her or show her that you think she’s sexy or cool. Women love the confidence it takes to show your interest.


2: Talk the Talk!

The way you use your voice conveys your confidence level, so cultivate a rich, resonant tonality. Record conversations with a friend and listen to your voice for flaws such as “uptalking” (when statements sound like questions) and excessive ums and uhs.

When speaking to a woman on your date, imagine another person is directly behind her and talk loud enough that both of them can hear you. This will help you project your voice, since chances are your voice shuts down a little when speaking to a woman you find attractive. (It’s a common unconscious reaction when we feel insecure.)

Think of a continuum of voice tonality, from supplicating (hesitant, quiet, uptalking) to neutral/friendly (your normal voice) to commanding (drill sergeant barking orders). Seek the sweet spot between commanding and neutral/friendly. This is the tonality that sounds firm and certain, yet friendly and upbeat.

3: Use Confident Body Language

Stand tall, widen your stance a bit, and take up space. When you stand, imagine that your spine is a steel rod.

Powerful body language not only sends women the right message—it boosts your emotional state. Try it right now: Stand up, hunch your shoulders, touch your ankles together, and hold that pose for thirty seconds. You feel small and passive, right? Okay, now stand TALL, like your spine is made of steel, push your shoulders back, take a wide stance, and hold this pose for thirty seconds.

I bet you feel more confident and masculine. That’s because adopting a confident body language can increase your testosterone and reduce cortisol, the stress hormone. 

4: Look her in the Eyes

I dated a marketing director named Olivia. After we’d been seeing each other for a while, I asked her what she liked about me on our first date, thinking she’d mention my smooth lines. But women rarely remember your words.

“That’s easy,” she said. “You looked me in the eye. That made you seem so confident.” 

5: Be Physically Expressive

Physical expressiveness is a simple, powerful way to create a fun, flirty vibe that keeps you out of the friend zone.

You can high-five, hold her hand, tap her arm, touch her thigh, whisper in her ear, or brush the hair from her eyes, among other ways—assuming, of course, that she’s made it clear that she’s comfortable with this, is enjoying it, and also reciprocates.

If you’ve gotten the “green light,” this is okay to do, within boundaries.

We’re humans. We touch. And for some women, physical touch is the main way they experience love and connection.

You want to be physically expressive in a way that makes her feel safe and comfortable. To help do this, have a reason for the physical contact. Just randomly touching her on a first date is weird. Make it an extension of your words and/or the emotion of the moment.

“What? You love Coldplay, too? Up high!” [High-five] 

“I have a secret to tell you . . .” [Lean in, whisper in 
her ear] 

“Your favorite movie is ‘The Mighty Ducks’? You need to go now.” [Lightly push her away]

Begin with small touches and taps on her arm or upper elbow. This gets her comfortable with your physicality, and lets you see if she likes it or not. If she clearly doesn’t like it or if you’re just not sure, then stop.) 

Physical expression is the stairway to intimacy with a woman you have chemistry with. Women HATE a handsy, octopus-armed creep. But in general, they love a man who’s comfortable being physically expressive while being aware of how she’s responding.

Connell Barrett is a NYC dating coach helping men worldwide date and find the women of their dreams. Connell has appeared on the Good Morning America, The Today Show, Access Hollywood, and more. Buy Connell's book, Dating Sucks But You Don't here.

You May Also Like:

How to Approach Women

What to Say on Tinder

What to Text a Girl

How to Talk to Girls

Dating in Your 40s as a Man

Connell Barrett Dating coach for men

I'm dating coach Connell Barrett. I help men build confidence and connect with women by being authentic!

dating sucks but you don't #1 Amazon bestseller

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NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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