Match her playfulness, then raise it one notch: a light tease or a specific compliment, delivered with a smile. Watch how she responds, and if she answers in kind, move toward a plan to see her. If she steps back, ease off. You do not need a perfect line. You need to show you noticed, you are enjoying it, and you are interested.
Make sure it is flirting
You cannot be certain that a woman is flirting. Signs include steady eye contact, teasing you, and touching your arm while she talks. She may lean toward you, find excuses to keep the conversation going, and ask personal questions.
Do not assume, though. Some women are simply warm. The good news is that your first reply is low risk either way: a friendly, playful answer works if she is flirting and works if she is just being friendly. You can adjust as she responds.
Match her energy
If she teases you, tease her back. If she is quiet and warm, slow down and be warm. If she is bold, be a little bold. The aim is to feel like a conversation between two people having fun, not a performance.
A woman who flirts is taking a social risk. Reply so she feels it was safe: smile, laugh when she is funny, and answer with something of your own.
Let your body join in. Face her, make eye contact, and keep your phone in your pocket. Let a silence last a moment instead of rushing to fill it. If you are both comfortable, a small touch such as a hand on her arm when you laugh is fine, as long as she is clearly welcoming it. If she steps away or stiffens, stop.
Raise it one notch
a dating coach gives a simple ladder. A statement is about the world. A tease is aimed at her. A flirt is about the two of you. You can climb it one step at a time.
For example, she says something funny about her bad parking. You say, "That was a ridiculous thing to do." That is a statement. Add "You are a ridiculous person" and it becomes a tease. Add "I am not sure we are going to get along" and it becomes a flirt.
The useful part is that each step is a test. If she responds well, you have permission to go one step higher with very little risk. If she does not respond, you stay where you are. My point is that you take no big risk at any point.
Keep it warm. The tease should make her smile, not feel small.
A specific compliment works as another notch. A line like "you look great" is easy to say and easy to forget. "You have a great laugh. It is a little bit dangerous." or "I like how you get excited about this" shows you are paying attention to her, not reciting a script.
Common mistakes
- Escalating too fast. Going from a joke to an intense declaration scares people.
- Turning serious. A flirty moment is not the time for your life story.
- Piling on compliments. Too many look like you are trying to earn a gold star.
- Ignoring it. Some men lock up and answer in a flat tone. Smile and say something playful.
- Over-explaining. If she teases you, do not defend yourself. Tease her back.
- Staying in play forever. Flirting that never leads anywhere is just entertainment.
Turn it into a plan
Flirting is more fun when it goes somewhere. When the conversation is going well, say what you would like: "I am enjoying this. Let us get a drink this week." or "You should show me that place you keep talking about."
Keep the plan specific, with a day if you can. A woman who is interested will say yes or suggest another day. A vague "maybe sometime" is a soft no, and you can move on easily.
The same steps work by text. If she flirts with you there, answer promptly but not instantly, keep it short, and keep it playful. Match her length, then add something that moves toward meeting: "We should settle this in person."
If she pulls back
If she changes the subject, answers in one word, or looks uncomfortable, ease off. Go back to a friendly, normal conversation. You can still be warm and polite.
Not every flirt leads to a date, and that is fine. A woman may have been flirting for fun, or may have changed her mind halfway through. A man who can take a step back gracefully, without sulking or asking why, is easier to say yes to later, and is far more pleasant to be around right now.
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.