Personally, I think you should grow your hair a bit longer; you know, 'bout 3 inches below the shoulder. Then, you should dye it with all sorts of colors! Multi-tonal, I believe it's called. Heheheheheh...then, you should cut off your balls and throw them away, it's obvious you don't need them. But seriously, that whole part about you making that "gorgeous" girl stumble into her friend was kind of a douche thing to say, wouldn't you think? I mean, we don't want to hear about how you woo these women, even if you actually do. We already have one "Ryan".
Just go buy some flanel jackets, grow out your beard and be a GUY. If you do all the crap you're planning to do to yourself...the only girl you'll get is you.