Girls don't go for the 'bad boy' as often as guys who can't ask a girl out imagine they do.
Girls go for a confident guy who doesn't passively aggressively dislike them. Girls do in fact, by nature, NOT like a wimpy guy. Or, as Than so nicely put it...pussies. Once a gal sees you that way, it's pretty much impossible to change that opinion.
Than respects the ladies, it comes across any time one of these discussions comes up. Can he be a jerk sometimes? Well I guess so, who isn't sometimes. But a gal will take a guy who is a jerk over a guy sitting in the corner crying to himself cause the gal he’s loved for 4 years still doesn’t notice him.
p.s. Good luck on your date. I have not been on a first date in...um...16 years, so I would very much like to know how it goes!!