This is some interesting insight the psychology of how to approach women on the street + do looks matter etc.

http://www.youtube.com/watch?v=QPDTOGRpuhw

Hope this video helps guys,

No they don't.

They like it when attractive, funny, cool guys approach them.

If a loser, creepy guy does it either A)creeps them out B) makes them think "Fuck I attract creepy guys" and/or C) I want to carry on my night/day, go away.

No, they like the idea of being approached, because they think "im attractive and people want to talk to me" then if a guy screws it up, THEN come the bad thoughts.

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Two words: Carpe Diem

Elaborate.

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KCCO

Speaking as a woman (which I am) - heed the following advice.
Approach woman on the street with caution.
It's a fine balance between appearing needy and cocky. Good looking women get approached all the time and they've heard it all before - you must not focus on her looks. Avoid complimenting her eg "You are gorgeous/beautiful smile etc etc"...remember lots of women don't take compliments well, it makes us feel awkward more than flattered (remember: there's nothing we can really say back to a compliment about our looks!) and a lot of time compliments may even sound insincere. Try and find something else to home in on. If I see a guy in the street I like, I try and grab some common ground between us - maybe he's looking in a shop window (I'll stop and make light conversation) or food shopping (make a jokey comment about should I get ready mix stir fry or make my own from fresh veg) etc.

The key bit is realising there may not be common ground and moving on. Women can tell pretty fast if a guy is their type. And lots of women dislike cocky, over confident alpha males and will run like hell from a full on approach. Some women like a softly spoken, polite, well educated gentleman. Try and get a measure of what sort of man she might like and tailor your approach to this and if it fails, walk. This is the not being needy bit. This is the difference between being the weird guy who hounded her on the pavement or the cool chap who made a friendly passing remark.