Hey cccrunner,
What kind of openers do you use?
With the experience I have doing this, I find indirect and situational openers to be the best for this type of "after hours" pickup. From what I've experienced, direct openers and openers such as "Are you single?" tend to fail pretty badly here. I think the reason for this is that women, at this point in the night, are
very used to being hit on aggressively by drunk men (who usually use direct openers since it requires that much alcohol for them to do so). Generally, their guards are up for "creepers" that pop up out of the woodworks since they are alone.
I still have a very sexy vibe when I approach them, but I try to make conversation first.
How fast do you have to escalate?
I actually do not escalate very fast at all in these situations. Chase mentioned to me that he had a mentor that would actually meet women after hours and take them somewhere private (meaning any nook or cranny) as quickly as possible and try to escalate there, so that method is probably possible.
From the times that I've had success, I've usually made sure to get a number quickly as I know the conversation could end at any minute if she suddenly gets that "phone call" from her friends that she's waiting for. After I've gotten the number though, a lot of times she'll just simply invite me to come with her to find her friends! Two weeks ago I ended up hopping in a cab with two gorgeous girls because the one I was talking to just pulled me along!
If she doesn't move anywhere, and I've grabbed her number, I'll sometimes just start to push for getting her out of there. This can be as simple as, "why don't we chill in my car where it's warm while we wait for your friends?" She will probably resist and insist on staying put, but the hard push technique can be effective here. Once she's in your car, then you can help her get "warmer..."
These are just a couple of examples of scenarios that happened to me, but I'm sure a million different things can happen since you're not stuck inside a bar or club. I would
highly recommend that everyone experiment with this. The great part about it is that you can still get your early momentum while you're still inside the bar or club as well as have a couple of drinks to get you in a relaxed state. From there, you can then come out and pick a woman up off the street before calling it a night!
If anyone happens to have some stories of their street pickups, feel free to share!
Cheers,
Franco