Is It Okay to Talk to a Woman on the Sidewalk or Subway in NYC?

Yes, it is okay to talk to a woman on a New York sidewalk or subway, as long as she is free to answer, free to leave, and you take her first sign of disinterest as the end. A short, friendly hello to a stranger is ordinary city life. What makes it wrong is pressure: standing in her path, cornering her in a packed car, following her, or pushing past a no.

Most of the etiquette comes down to one question. If she does not want to talk, can she end it easily?

On a sidewalk, she usually can. She keeps walking, and you let her. On a subway, she often cannot. The car is a closed box, the next stop may be two minutes off, and moving away from you means making a scene in front of strangers. That is why the same hello that is fine on Prince Street can feel heavy in a crowded train.

So the subway is not off limits. It just asks more of you. Keep it lighter, keep it shorter, and pick your moment with more care than you would anywhere else.

A woman who is standing still is easier than a woman who is walking. Look for the natural pauses the city gives you: waiting at a crosswalk, looking in a shop window, standing outside a cafe, sitting on a stoop or a bench.

If she is walking, you can still say hello, but do it without making her stop. Fall in beside her for a moment, at her pace and at arm's length, say what you have to say, and let her decide whether to slow down. Never step in front of her or walk backward in her path. a dating coach notes that many people on New York streets have headphones in or are moving through crowds where it is hard to reach anyone. A woman with both earbuds in and her eyes on the pavement has told you something already. Let her go.

Parks are easier than sidewalks for the same reason. A woman on a bench in Washington Square Park has stopped on purpose.

The platform is better than the car. People waiting for a train are standing still, a little bored and not yet boxed in. A comment about a delay or the book she is holding is easy to answer or ignore.

Inside the car, the crowd decides it. In a rush-hour crush, do not try. She is pressed against strangers already, and adding a conversation she cannot escape is the opposite of friendly. On a half-empty train in the middle of the day, sitting or standing near each other, a light comment is fine.

Watch the stops. If she is getting off, let her get off. Do not change your route to leave at her stop and walk after her up the stairs. If the talk is going well and you are both getting off at the same place, you can keep chatting as you walk out. Otherwise, a quick "nice talking to you" as the doors open is a clean ending.

New York has a reputation for cold people, and the street often looks that way. In practice, the city is full of people who moved there recently and are still looking to meet others. a dating coach, who has lived in New York, says people there are more social when they are out than in many other cities for exactly that reason.

There is also less at stake than you imagine. In a city this size, if a hello goes nowhere, you will probably never see her again. The awkward moment lasts a few seconds and is forgotten by both of you by the next block.

A few things turn a normal hello into something she has every right to dislike:

• Comments about her body, or anything said loudly enough for the car to hear.
• Touching her, even lightly on the arm.
• Asking where she lives or which stop she gets off at.
• Following her after she has walked away or gotten off the train.
• A second try after she has said no, or asking why.

Avoid all of these and you are doing what thousands of New Yorkers do every day without anyone thinking twice.

Ending politely is part of whether it was okay. If she gives short answers, looks away or says she is busy, say "no problem, have a good one" and leave. If it goes well, ask for her number or Instagram within a few minutes rather than riding the whole line together. Keep it easy for her to say yes and just as easy to say no.

Whether you are coming across as relaxed or as pushy is hard to judge from inside your own head. Cold Approach runs its Bootcamp in New York and Miami, with two four-hour blocks in the field each training day, daytime approaches and nightlife mixed to suit you. A coach watches each approach and tells you right after the set what your pace, distance and timing looked like. Beginners are welcome, and approach anxiety is the specialty.