Successfully starting up a conversation with a woman in a bar can be challenging, but stopping a woman on the street and getting her to give you the (proverbial) time of day takes a special kind of skill set. If a woman is at a bar, club, party, or any social event, for that matter, she will usually be quite open to making small talk with guys. When a woman is on the street she is usually on her way somewhere. She is not likely to be in a social state of mind, and may even be on the defensive. This is especially true in urban areas where the streets are crowded with people.
Bring Your “A” Game
Needless to say, the odds are stacked against you in this scenario. Unless you make a flawless approach and come across as likeable and trustworthy in the first two seconds of the conversation, you will more than likely be ignored (or worse).
I lived in Brooklyn for a year, and during that time I commuted to Manhattan every day to attend class. On any given day there was construction going on somewhere on my route, and I would inevitably hear a construction worker whistle like a dog at an attractive woman an utter something along the lines of “Hey, sweetheart, what’s the hurry, come see me baby”.
My guess is that I witnessed a scenario like this at least 100 times that year and the result was always the same. The woman kept walking as if she was a deaf mute.
The point of my short anecdote is that the Neanderthal approach is a waste of time. It will only produce failure, so you are going to have to come up with something a bit more refined. Every encounter is unique, so there are no hard and set rules to picking up women on the street, but the following tips are a good place to start.
A Plausible In
In a bar you could sit down next to a woman and chat with her for no reason, but if you stop a woman on the street you should have a reason, even if it is only an icebreaker. If you start with a come on, the woman’s natural reaction will be to blow you off. Your goal is to start a conversation, and keep it going long enough to make a good impression and get her phone number. You can ask for directions, the time, or even whether she thinks your shirt and tie look good together.
The reason you stop her is less important than the way you do it. You want to be polite, but confident; friendly, but not invasive. This may sound difficult, but in reality it is actually very difficult. If you come off as nervous, rude, overly aggressive, insensitive, intrusive, or oblivious, the conversation will be a short one.
The Golden Rule
The trick here is to imagine the girl you are stopping is someone you have met before, but do not know well. Be friendly, but do not assume too much familiarity. Smile and make eye contact, but do not cross the line and touch her. Keep the conversation light so you do not scare her off, but make it clear you are enjoying talking with her. This is quite a balancing act to pull off, but with a little practice you should see your success rate drastically improve.