i partially agree with juang. although the "cocky and funny" thing doesn't seem to work. i tried a couple of times the "make fun of her as a joke, she'll laugh", but every single time, they just get pissed. so i don't recommend that.

PS: yea i definitely used to be the wuss. and just thinking about it sucks. you definitely need to man up. and if you're chasing a girl now that you've been a wuss with, you definitely need to abandon it. most likely won't work.