How to Approach a Woman at a Place Where You Are a Regular

Do not walk up to her table. A girl sitting alone is the easiest approach there is, but when the place is yours and you will be back tomorrow, it gets awkward fast. The better way, which our coaches gave a student who asked this about a coffee shop where they were a regular, is to approach her while she is standing in line. Get in line behind her, say something ordinary about the moment you are both in, and keep the whole thing slow and relaxed. You are not trying to look bold. You are trying to look like a man who happened to be there.

A man on a street corner can say something to a girl and walk away, and nobody will ever remember it. At your own coffee shop, the staff know you, the other regulars know you, and she may well be back on Thursday. Whatever you do is going to be seen again.

The student who asked on our call worried about the same thing. Going direct or flirty from the start would feel uncalibrated, and an indirect opener would feel out of character. A bold line from a man the whole room knows as a regular can look strange. A sitting girl is also a little stuck. She cannot step away easily, and every other regular is a few feet from the conversation.

The coach's answer was simple. A girl waiting in line is doing nothing, she is standing, and she can walk away from a conversation easily. If she is queuing and you join the line behind her, you have a natural reason to be next to her. It is the least try-hard way to open that exists, because nothing about it looks like an approach until you start talking.

Even if you already have your coffee, you can use this. The coach's example was to split what you buy. Start with the coffee and sit and work. When a girl you like joins the line, get up and get in line behind her for the pastry. Sit down again, and later get up for water. You have created three separate chances to stand next to a woman, and none of them looks like it was planned.

The coach told a story from their own student days that shows how far this goes. Every time they stood up to get food, there was a new opportunity to talk to a girl. So instead of collecting a whole meal at once, they bought it in parts: one item, then sit down, talk to a girl and eat it. Then back for another item, and the same again. One meal became about three sittings, and about three approaches.

The point is the design, not the cafeteria. If you are going to be somewhere often, build the visits so that standing up and crossing the room is normal for you.

On the same call the coach gave a general rule for places where people know you: escalate slower than normal, be less gamey and less try-hard, and be more patient. The reasoning is that you have more to lose socially, and also more chances if it does not happen right now. At a bar you will never visit again, an interaction that does not move today is over. At your regular spot there will be a next visit and a visit after that, so you can afford to take a smaller step each time.

The coach also said to keep it less public and to get her participating more. Let her take part in the conversation, ask her questions, and do not push her to a decision in front of the barista. A small exchange at the counter and a pleasant nod next week is a good result.

There is a limit. On a question about gaming on a college campus, the coach said not to game one location so much that you over-game it. A place where people know your face can take only so many approaches before you become the guy who does this. Spread them across other places, and keep your regular spot for the one or two girls you actually like.

Take the first sign of no at face value. A short answer, a glance at her phone or a step away from you is enough. Say thanks, finish your coffee and go back to being a normal regular. The whole reason this approach works is that it costs you nothing to leave. If a refusal makes the place uncomfortable for you or for her, you did it too hard.