Cowsgomoo, you are hideously correct, and hilariously awesome.
It's hard, but you really have to stop caring about what is going to happen. Part of the problem is that guys have been conditioned through countless media outlets (movies, books, tv shows etc) that the guy who gets the girl is quiet, respectful, and when he finds the right girl, unrelenting about his utter love for her. This couldn't be more wrong. People like challanges. A girl isn't going to be smitten by a guy who meets her, and then starts calling her every day, going out of his way to do things for her and will drop everything at the drop of a hat. That's BORING. You have to make the impression that you MIGHT be interested, but make it so they're not 100% sure, (i.e. flirt, joke around, tease them) but at the same time, don't overdo it. There's nothing more painful to watch than some guy who is flirting wayyyy too hard, and the girl is obviously not interested, because once again, it's too easy for them.
In a horribly twisted way, I was TOO good at that. I would flirt and have fun with girls, but I was too shy to actually try anything, so I would always stop short of asking them out. Years later, I would get calls from these girls looking to, "catch up." I would always be told something to the effect of "why did you never ask me out? I used to have such a crush on you, and I thought you felt the same way." I would look at them, smile and laugh politely, and mentally kick myself every time I heard this.
Basically, what I'm trying to say is: Just go for it. If it dosen't work out, you'll be a little embarrassed, but it's not the end of the world.
It's hard, but you really have to stop caring about what is going to happen. Part of the problem is that guys have been conditioned through countless media outlets (movies, books, tv shows etc) that the guy who gets the girl is quiet, respectful, and when he finds the right girl, unrelenting about his utter love for her. This couldn't be more wrong. People like challanges. A girl isn't going to be smitten by a guy who meets her, and then starts calling her every day, going out of his way to do things for her and will drop everything at the drop of a hat. That's BORING. You have to make the impression that you MIGHT be interested, but make it so they're not 100% sure, (i.e. flirt, joke around, tease them) but at the same time, don't overdo it. There's nothing more painful to watch than some guy who is flirting wayyyy too hard, and the girl is obviously not interested, because once again, it's too easy for them.
In a horribly twisted way, I was TOO good at that. I would flirt and have fun with girls, but I was too shy to actually try anything, so I would always stop short of asking them out. Years later, I would get calls from these girls looking to, "catch up." I would always be told something to the effect of "why did you never ask me out? I used to have such a crush on you, and I thought you felt the same way." I would look at them, smile and laugh politely, and mentally kick myself every time I heard this.
Basically, what I'm trying to say is: Just go for it. If it dosen't work out, you'll be a little embarrassed, but it's not the end of the world.

- plenny more where that came from 