let's redefine what a jerk is not.
Paying for someone else you barely know. You wouldn't give 20$ to a homeless beggar would you? So why should you spend 20$ for a meal or a gift on a woman you've just met? I've done it plenty of times and I've not done it plenty of times, but I only do this sort of thing if I want to, I def. don't feel like a jerk when I decide not to do it. And I never do this anymore because it takes too much time to eat dinner out somewhere.
Not being overly nice. I'm not sure what this is even about. I am always nice, but I don't act like a p*ussy guy. If one is so worried about getting a negative reaction that he's about as much fun to talk to as Bob Dole, I can imagine that's a real issue to address. I think the issue here is just to be confident enough to be cool (no need to stress) and express one's own sense of humor.
Ask yourself this: What would a woman want with someone who is boring, super feminine (she's not a lesbian or she'd be out with a woman), or grosses out all her girlfriends?
Every since she was a little girl the media & society have been putting a different idealized image in her head. Football players, successful bussinessmen, crazed rockstars, "OC" type guys, artists, and basically a guy that is perceived as having choices in life and someone who will make her girlfriends jealous. I'm not saying people should change who they are and pretend to be someone else, but I am saying it's worthwhile to take inventory and make certain one is not afraid to show who is really is in order to "not screw up his chances". Look at all the examples I listed above, basically there is a broad spectrum of personalities and styles that are broadcasted as attractive. everyone fits into one or more of these categories if they only realized it. In other words, lowering one's defenses and anxieties makes good sense.