I think ThrowDown's suggestions are pretty good, however I attack it from a slightly different angle... firstly you can check PrettyDecent on what he calls "singular flow" or something similar (can't remember exactly), which means basically keeping your conversation relevant to the situation (at least initially) so that it's not too jarring for her. For me that translates to asking them a bit about their day, how they got to wherever they are and where they're going.
But, and this is a big but, you can't just do it in a 20-questions way, you have to cold read them based on what you see. For example... it's 12:30pm and she's wearing a business suit and carrying a Uniqlo shopping bag...
Me: hi there, I noticed your cute scarf and I just had to stop you and introduce myself... I'm Ray
Her: I'm blahblah, nice to meet you
Me: looks like you just stepped out from the office for a quick shop, you needed something in particular?
Her: oh no actually I was just killing a little time as my meeting finished early
Me: oh really? so I guess you have a lunch to attend in a short while, a business lunch...?
Her: yeah that's right I have to entertain a client
Me: okay nice work if you can get it! so by the looks you're in financial services or something of that nature
Her: yeah I'm a business analyst... blah blah blah (she finally starts to open up)
So whatever she tells you you just add it to your store of knowledge about her and then use it for further cold reading... note I did actually phrase some of the lines as questions above, but I would use a tonality that makes it almost a statement...
-Ray[/quote
]
ThrowDown said:
Suave.. After the opener, Introduce yourself then ask her about a certain type of clothing or jewellry she is wearing. "That's an interesting scarf.. It would look better on me" adds a little bit of self deprecating humor, teasing and flirting. If she isn't wearing anything that catches your eye, transition from opener to a socially acceptable convo according to the environment.
I.e. Coffee shop.
"Yuck this coffee is terrible"
Or school, "so what are you taking? Biology? That's a horrible choice.."
Mall:
"You really don't have to buy me a gift.. It's not our anniversary yet!"
Street: "I seen you following me down the street.. Must be that stalker lady who's been texting me for nudes!"
DONT OVERTHINK IT. My rules are. Don't give a fuck, and get out there and do something that will make yourself smile. Approval seeking behaviour is for nice guys.