Healother, I have come to the conclusion that you:
1. Are Emo;
2. are an Emo Alter;
3. or you just WAY overanalyze shit.
Stop thinking so much and start enjoying life a little. Date, kiss, have sex or not, fall in love a few times, get your heart broken and maybe break a few hearts. You haven't lived enough to know what you want or don't want, and you can think about it until the sky caves in and you won't KNOW what it's like unless you live it.
Someone could tell you what it feels like to bungie jump, but it's JUST NOT THE SAME THING as doing it. You will NEVER know what it's like unless you jump off that bridge yourself.
The reason we live is so we can learn. The reason we make mistakes is so we can learn. You can't make mistakes unless you get out there and get your feet dirty with some real living.
So stop trying to think of what women think of you (because you'll NEVER figure it out anyway), stop trying to figure out what's going to happen before you even make a move (i.e., stop mentally getting married to a girl before you even go out on the first date, stop anxietizing over how a date may or may not go with women you haven't even met) and just get in there, swing for the fences and have some damn fun.
In other words, stop overthinking shit. You can't possibly work out hard enough, you think to friggin' much. If you lifted more you'd be too damn tired to think so damn much.