Should You Approach a Woman at Night From Behind?

No. If a woman is walking alone at night and someone closes in behind her, she is frightened before he has said a word, and nothing you say next will undo that. Even if your intentions are completely friendly, she cannot know that. Leave her alone on a dark street, and save your approaches for places where she can see you coming and other people are around.

She cannot see you. At night, on a quiet street, the only information she has is footsteps that are getting closer. Her mind does not wait to find out whether you are charming. It decides whether she is in danger.

That reaction is reasonable, and it is not about you. A woman who walks fast, crosses the road or grips her keys is protecting herself, and she is entitled to. If you caused that reaction, the approach has already failed, and the right response is to back off and let her go.

So the question to ask is not whether you can do it smoothly. It is whether it is fair to put a stranger through that in the first place.

Night is fine as a time to meet women. The problem is the setting, not the hour.

Bars, restaurants, parties, events, the line outside a venue and a busy lit square all give her what the dark street takes away: other people, light, and an exit. In those places she can see you before you speak, look you over and decide how to react. Walking up from the front or the side, with a smile, is normal there.

Open the way you would in daylight. a dating coach's advice is to come from a distance that gives her time to take you in, speak loud enough to be heard and plant your feet. In a crowded venue, "Hey, excuse me" works the same as it does anywhere.

a dating coach does teach three ways to stop a woman in the daytime: from the front, from behind, and walking with her. His version of stopping from behind is a light tap on the shoulder from about arm's length, then a step back to give her room when she turns around. Then he stays calm, plants his feet, and eases into an ordinary conversation.

Everything about that depends on daylight and people. It is a street full of other pedestrians, a store, a station. It is not a quiet road after dark, and it should not be used there.

a dating coach also warns about angle. When you walk with a woman, he says to merge into her path rather than cutting across it at ninety degrees. He also says to avoid coming at her side-on, because that comes across as aggressive. All of this is daytime advice for a woman who can see you and who is surrounded by other people.

Sometimes you have a reason: she dropped a glove, or left a card on the counter. Then keep your distance. Call out from several steps back, in a normal voice, so she hears you before you are near. Say what it is: "Excuse me, you dropped your glove." Stay where she can see you, keep your hands visible, and let her come to you.

Do not follow her to make a point of it. If she goes quicker, let it go.

Watch what she does. If she speeds up, crosses the street, pulls out her phone or clutches her bag, stop at once. Say "sorry, I didn't mean to startle you" from where you are and turn away. Do not explain yourself at length, and do not walk after her to check that she is okay. The kindest thing is to give her space.

Then think about why it happened. Not because you are a bad man, but because the setting made it impossible for her to feel safe.

If you want to meet women, go where it is easy for them to say yes. A bar or event in the evening, a class, a market, a coffee shop in daylight. Look for the woman who is looking around, smiling and facing the room. Make eye contact first, speak first, and give her the choice.

That is better manners and better results. A woman who sees you walk up openly has time to feel curious, and curiosity is what you are after.