Tease the small thing she said or chose, not her. Make a playful guess about her coffee order, her strong opinion on pizza, her habit of being late, and let her answer. A good tease over text is one short line, with a smile you can hear, that she can fire right back at. If she would not laugh when you said it out loud, do not send it.
Why teasing works at all
A tease tells her you are comfortable enough to joke with her. It also changes the energy of the conversation from two people trading facts to two people playing.
That is why men who only ask polite questions get flat replies. "What do you do for fun?" gives her homework. "You look like someone who has strong opinions about hot sauce" gives her something to push against.
coach teaches a few simple lines for this, such as telling a girl she looks like trouble or that part of you likes her and part of you does not. What they share is that she has to answer, and the answer is more fun than a "good, you?"
The text version has one big problem
She cannot hear your tone. A tease that works with a grin across a table can look mean on a screen.
That means the margin for error is smaller. Keep the joke gentle, keep it about something light, and let the wording carry the smile. A short, exaggerated line does this better than a clever one.
Teasing examples that work
Guess something small about her taste.
She says she is making a big salad for lunch. You write: "Let me guess, you also have a very serious opinion about dressing." She can answer, or tease you back about your own lunch.
Pretend to be suspicious of her.
She tells you she is "not a morning person." You write: "That is exactly what a morning person would say to keep the good parking spot." It is silly enough that it cannot hurt.
Turn a small thing she said into a running joke.
She mentions she has never missed a flight. You write: "Noted. Never booking a trip with you, you would make me get there three hours early." Next time travel comes up, you can bring it back.
Take her teasing and send it back, a little bigger.
She writes: "You are so trouble." You write: "I have a reputation to protect, please do not tell anyone." You are not defending yourself. You are playing along.
Rules that keep it friendly
Tease choices and habits, never anything she cannot change. Her job, her family, her weight, her looks, her intelligence and anything she has told you she is insecure about are off the table.
Keep it short. A long tease reads like an argument.
Do not explain the joke. If you have to write "just kidding, haha, I was joking," the joke was not good enough, or you do not trust it. Pick a different one next time.
Let her tease you back, and take it well. If you can laugh at yourself, the whole exchange feels safe for her.
How often to do it
A tease or two in a conversation is plenty. Mix it with plain talk, a real question and something about your own day.
If every message is a joke at her expense, the conversation becomes a performance, and she has to keep up with it. Teasing seasons the conversation. It should not be the whole meal.
When to stop
Watch what she sends back. If she answers with a laugh, a counter-tease or a longer message, keep going. If she goes quiet, gets short, or writes something like "that was not nice," stop the bit, say "fair enough," and change the subject. Do not defend it and do not repeat it.
One more point: teasing is a way to add spark, not a way to get a woman to accept being disrespected. If you are not sure it is landing as a joke, switch to a straight, warm message and try again in person, where she can see your face.
Written by Matthew Stevens, Co-Founder & Head Coach. More than half a decade coaching men across the US and worldwide.
Everything here comes out of real coaching work: the approaches, dates, texts and profiles we go through with the men we coach.