How to Flirt with a Woman You Don't Know

Say something true about the moment the two of you are sharing, add a playful twist, and keep your tone relaxed. That is flirting with a stranger, and it is also the answer to what to talk about. You do not need her life story or a clever line. You need one honest remark about what is happening right now, said like a man who is enjoying himself. The same works in a first message on dating apps.

A woman you have never met has no opinion of you yet. Nothing you said last week is counting against you. Whatever you do in the first thirty seconds sets the tone, and a friendly, unhurried man is a rare enough thing that she notices.

Most men lock up because they think flirting means producing a smooth line. It does not. My version is much smaller: pay attention to the world around you and say what you see. If you can describe the room, you can flirt.

My first technique has two steps. Notice the first unusual thing about the moment, then invent a reason for it.

Something is always unusual, because every person reacts a little differently. If she says hi back with a huge smile, that is unusually friendly. If she looks at you like you asked for a kidney, that is unusually suspicious. Either one is material.

Then give it a made-up explanation. "You are way too cheerful for a Tuesday. Did you just win a raffle?" She did not win a raffle, and that is the point. You are being playful about her, which is exactly what flirting is.

If you want to push it further, ask what else would be true if your explanation were real. If she just won a raffle, she is probably about to spend it badly. Exaggeration is where the fun comes from.

This one comes from stand-up comedy. Name two ordinary things, then break the list with a third that is a surprise.

"Do you spend your weekends hiking, reading, or ruining the lives of men in coffee shops?" The first two set up the expectation. The third one breaks it and tells her you see her as a woman, not as a stranger who needs directions.

You do not have to be a comedian. Two plain items and one silly one is enough, and the structure does half the work for you.

A plain compliment gives her power and takes nothing back. My fix is the push and pull: put a positive and a negative in the same breath. "You have a great laugh. It is going to be a problem for me."

She hears that you like her, and she also hears that you are not melting into a puddle. That mix is what makes it feel like flirting and not like flattery. A line like "You seem like exactly the kind of girl my mother warned me about" works the same way, because being warned about is a flattering thing.

Keep the topic close to the moment you are in, and keep each message to one idea. Ask about what she is doing there, what she is carrying, what she ordered, what that sticker on her laptop means. These all give her something easy to answer and something you can tease.

Avoid the interview. If you fire "What do you do? Where are you from? Do you have siblings?" in a row, she will feel questioned. Swap one of those questions for a light opinion: "You look like someone with very strong views on pastries."

If a topic goes well, stay on it. Do not jump from something fun back to the weather, because you will have to climb back up to where you were.

On a dating app you have even more material, because the matched photos and text are right in front of you. Use the same method. Notice the unusual detail, give it a made-up reason, and ask a question she can answer in one line.

Keep it short. My rule for texting is one or two ideas at most, because a wall of text from a stranger looks needy and is tiring to answer. A friendly, teasing first message beats a paragraph every time.

Flirting with a stranger only works if she can leave easily. Watch what she does with your remark. If she laughs, answers with her own tease, or asks you something back, keep going. If she gives a polite one-word reply and looks away, thank her and move on.

You are not trying to win her over in that moment. You are finding out, cheaply, whether there is any spark. A man who accepts a quiet no gracefully gets a second look from the next woman he speaks to, and from the people watching him do it.