Well, I don’t have much experiance in this department. What is a good way to break the ice?
We’ll need details.
Just to start things off, however, I’ve always been fond of the simple approach: Hi, I’m Blue. Then talk about somethig like the weather, whatever is simple and convenient, then mention casually that you have tickets for <whatever>; would he/she like to go? Yes? wonderful!
Cake and pie.
“I’ve got money.”
Find something of common to talk about casually. Try to find something more original than the weather. Draw him/her into a conversation. Then say “would you like to go to x with me?”
Jump right in! It will all end in tears anyway. 
Yep-best to ask about a specific event in mind–NOT, “would you ever want to go out with me?”, which could elicit a hurtful response.
And fer cryin’ out loud, smile when you ask. Smile and walk away when you’re turned down. Beam when you’re taken up on it.
Practice at home, first, if need be…
Nothing succeeds like having a lot of money. Unless it’s having a lot of money and good looks.
Duct tape and plenty of rope.
With confidence.
“Nice shoes, wanna f*ck?”
I’m afraid that you won’t find any easy answers, especially on a news group. A good way to break the ice is to say hello, my name is. Smile. Ask her about her. Be sure that you are genuinely interested, not just faking it to get laid.
Beyond that, it takes some practice. There are some books that might help, but then maybe not. A popular one now is called The Game, but only a brief skim of it seemed to me that the author didn’t like women, but liked the feel of everyone thinking he scored a lot. None-the-less, it may help you learn to break the ice.
There is a book called USS that is written by a woman about what makes women tick. It claims to be scientific and lays out steps to helping men meet and hook up with women. Dunno if it works.
Back to the practice thing. Understand that not every woman in the world that you like will like you. Get used to the idea that you may be rejected and get over it.
Good luck.
assuming it’s someone you’ve met and have had conversation(s) with before:
be very casual, talk about other stuff as though you’re not leading into anything in particular. then smile and say something like “ya know, you’re a pretty cool girl (/guy); we should hang out sometime. you free (such-and-such a time)?” be prepared for either answer. if they say no (and don’t suggest another time), like someone already said, smile, maybe a little shrug, “that’s cool”, go on about your business without acting uncomfortable. if they say yes, have something specific in mind to do-- this way they don’t have to think about when, where, or what; the only thing they have to decide is whether they want to be there with you, and that’s what you want to know.
if it’s someone you have not yet talked with:
I advise strongly against it. you need to establish some kind of rapport first or it’ll probably come off as more than a little creepy, the exception being if they’ve been eyeballing you all night/week/month/whatever. if it’s someone you see out somewhere and think you’ve got to go after then & there or you may never see them again, I guess the best approach would be to use a shortened version of what I said above. strike up some kind of conversation (preferably not starting with a pickup line), bullshit a minute or two, pull the same “you’re cool; let’s hang out” bit.
in all situations, de-emphasize the “date” aspect. you don’t want it to seem that way until an attraction has been firmly established; otherwise there’s this weird artificial pressure and all these rules and boundaries, when you could just be having fun.
good luck! 