I think I do a pretty good job of it; I flirt and try to be funny and it seems to work. Problem is, because I'm not very good-looking, I'm usually automatically friendzoned at the start so then I just become the funny/flirty guy you have fun with. It kinda sucks to see these same girls ogle over good-looking guys, they get the automatic advantage while I have so much ground to make up and constantly make up to keep up, but that's just how it goes.
Oh yeah, and a bigger problem is that even girls I'd consider my level looks wise will still auto-friend me and then go for the better-looking guy (understandable). It just sucks.
It's not a coincidence that many driven, goal oriented, successful guys are elusive to a lot of girls. It's because they are usually taken off the shelf, regardless of their appearance or lack of "mack skills" that some guys assume is needed to get women. I'm not equating success with riches either, so don't get me wrong.
The fact is, many girls like to associate themselves with successful guys. Find something that you enjoy doing professionally (if you haven't already), then become successful at it. Your confidence will increase, and thus your results with the ladies will as well. Success can help you level the playing field.
Hmm, girls like friendly guys, but being too friendly can maybe be the problem. Try maybe to tease a bit and some jealousy?
You know, giving them attention at first but not too much them, so they might ask themselves what's happening. Playing hot and cold may result.
At least it happened to me having some friends that I wouldn't consider dating because there was no chemistry. But I can assure you when they stopped giving attention I would try to know what was going on and probably take the lead.
AND: confidence. It's very attractive. You don't feel confident about how you look? Change it, looks can be changed. Still doesn't work? Act like if you feel confident about it. People can't tell if you're pretending, and after some time if it works you'll feel truly more confident about yourself!