[WildChild]

isnt this the same as my initial suggestion of approaching randomly - i might be noticing her on a regular but is she noticing me?!

If you talk to her, she will be.

[Hopeless Dork]

I agree that the best approach would be somewhere where you see a gal on a regular basis. A coffeeshop is pretty neutral and safe place to say hello and chat someone up. A friendly hello, how's your day going is nice.

Completely agree with this. A cold approach on the street, just walking up to some random chick and telling her she's pretty and introducing could lead to some uncomfortable situations. You know nothing about the woman, she may have a boyfriend, she may not be interested in men, she may be having a really bad day and isn't in the mood, she may have had 3 guys already approach her the same way and any of those scenerios could lead to her being rude if she is the kind of girl that gets hit on often.... which is generally the kind of girl guys want to hit on

Approaching someone cold, by that I mean knowing nothing about them except for the fact you think they are hot puts a woman immediately in the position of feeling like you are going up to every pretty girl you see, it can come off desperate or like a player or superficial and none of those things tend to lead to a date in most cases. Unless there is a STRONG mutual attraction.

When you do like what sourpuss says, approach a woman in a setting where they are stationary, you can take in something about them that has nothing to do with their looks and be able to start a conversation that may gain her interest. Oh I see you ordered the blah blah blah... any good? I wanted to try that! But just some random woman walking past minding her business, stopping her... your motives are ultra clear and it can come off way too strong.

Being approached by a man at night when I'm alone is SCARY... no matter if the guy is cute and nice.. its awkward and uncomfortable and does not feel safe. No matter if he is 'normal' looking you still fear for your life for a few seconds and that is probably not the first impression you want to give a woman. And unless she is stopped you are having to keep up with her pace and having someone walking up fast behind you, again, scary.

[kristalyn_04]

Yeah admittedly if a guy did that to me I would assume he is a creep or trying to get something from me, and I would immediately assume a defensive stance and give him a warning to back off or I would hurt him. Now I am able to defend myself, but not every female can and would understandably be scared if a guy approached them on the street. You definitely don't want that kind of first impression. You want to approach women in a neutral setting; on the street is not neutral, it's vulnerable for a woman.

[deadharbor]

I get approached alot because I live near an Asian school and I'm Asian (I get the same pick up line too - "I used to teach English ...". It's unfair maybe, but I don't like it. I like the bookstore approach a little better. Totally random is just not very attractive. If you pass this girl daily, maybe that's a little better. I think she just have to get used to seeing your face, at least a few times before you approach her, or it would be kinda weird.