^ Lolz.
My usual stratagem when engaging in a conversation is to try and make them laugh. This is usually achieved by taking whatever they've said and using past experience with the subject they are talking about, and giving it a comical spin. Flirting target then laughs, as they can relate to the joke I told. If they don't laugh, I count it as a first strike. If they get three strikes, I cut my losses and back off. If I can continually make them laugh, I progress to the next stage and slip phone numbers/IM into the conversation. Either saying something along the lines of, "msn is playing up for me. How about you?" If they reply in a way that confirms they have said IM, I'll swallow my pride and be like, "Oh, you have msn too? Cool, mind if I have it?" After that, who knows.
I try to be obvious about my intentions from the beginning, without being too brusque. I drop ambiguous hints that can be interpreted in a number of ways. If they seem receptive, I kick it up a notch and become more forward in my actions, but not too strongly. If they pick up the hint but indicate disinterest, I back off. No harm done. It's not as if I directly came on to them, only to be rejected.
That would be incredibly awkward for both parties. With my method, both parties know where they stand, without the need for confrontation.
This is my tactic, should I be the one doing the chasing. But it seems I have rarely ever used it, as I'm the one usually being chased. I don't really look for relationships; I occasionally stumble upon opportunities and either choose to seize them or let them pass.
ETA: I don't know if my post implied that I have high levels of confidence in my romantic pursuits, but I just thought I'd add that it doesn't included the emotional side of my endeavours- I'm usually proverbially crapping myself and my instincts tell me to run away and never look back. Of course, this isn't considered a very attractive trait for most people, so I hide it behind a stiff upper lip, a daft grin, or a clacking of the keyboard (most commonly).
