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It can work with less attractive guys, but you've got to be starting with a woman whose sense of attraction isn't purely physical. Like their male counterparts, those kinds of women are more interesting and smarter anyway.
Aaaand I suppose this is where your older woman thing comes from, now that I think of it. I won't deny the younger stock -- of either sex -- is rather superficial.
At a bar, you're not likely to meet women (or men, if you're a woman) like that. In the bar game, it's strictly numbers. Nines go home with nines. Sixes go home with sixes. Now if you have some good immediate game, you can swing the numbers your way favorably (albeit slightly), but a 4 isn't going home with a 9, even if he has a tongue so silver that jewelers would grade it.
I've always been able to attract women that are probably somewhat not in my league, but that's because of my ability to talk to them. However, there are limits. I'm not going home with the prom queen, no matter what game I spit.