Rejection, have you met my friend fear?

There's a fellow. There's always some fellow who I imaginary date and feel imaginary happy with. It happens in an instant. A fellow comes into my work, and with him, he carries that thing, that 'I'm comfortable in my own skin' thing that draws me in. He takes my breath away, not in a Romantic novel sort of way, but in a literal, uncomfortable, I-need-my-air-back way. I blush and try to recapture the composure he's stolen from me. He is handsome, but I honestly don't care, so long as he just keeps wearing himself like a favourite sweater. He's got something lovely I hope is contagious, some sweetness I want to be near.

One day, I force myself to talk to him, because the possibility of letting him slip away and be unbearably great somewhere far away from me is impossibly unbearable. I'm aware the whole time we're talking that the words are slipping out of my mouth like wet soap, that he's making something physical and silly to happen to me, that maybe he could become more than daydreams to me one day.

He'll come in and out of my daily life, and have no idea how many times he has imaginary held my hand.

Months go by.

There are other fellows, some gentlemen, some not, who try to woo me in the meanwhile. I hate knowing already that they are not for me, but you know when you know. I go on some bad dates and try to stumble graciously out of second bad dates without hurting anyone. I have a boyfriend for a little while, and he is handsome as can be, and smart, and really wants to know me, but he's also a little too selfish and hurt from past loves, and we break up. Then come some serious changes to my life, and there is little room for daydreams and the fellows who inhabit them, because my heart is instead breaking for someone closer to home who needs me.

And then, through some weird snap of luck, the fellow somehow, after two years of intermittent and imaginary courtship, is in my life in a real and unromantic capacity, and he's sitting in front of me,talking to me, asking my opinion on things, and it all seems so unreal and tenuous because all I want to do is impress him. I want him to think I'm neat. And in moments of bravery and feeling hot, I convince myself I'm going to take some kind of risk. Bolstered by coffee and the advice of encouraging friends, I prepare, look at all the angles. I even imagine the conversation we might have(don't pretend you don't)

me: Hi, um, you there, do you want to go out sometime?(a little vague, lacking finesse, I know, but I'm nervous and trying not to pee myself like the perps do on NYPD Blue when they're being interrogated)
him:Oh, geez, (because I think he's the type to say 'geez') I'm terribly flattered, but, um, I don't think it's a good idea...
or
him: Oh, gosh, that's awfully nice of you, really, but I'm seeing someone.
or
him: Oh, good heavens. No.(head shaking vehemently)
or, finally,
him: EEEEUUUWWWWW.

I know. He won't say that. But this is what I do when I'm scared. I try to familiarize myself with the negatives, examine them critically, because maybe if I get used to them, they won't scare me so much. Right? Right? Only I am scared, pull-the-covers-up-tight scared of the possibility that he will reject me. Scared of being so naked with my want, and naked with my disappointment. Scared of what's on the other side of rejection. I'm so scared of the hundred or so crash and burn scenarios I've 'familiarized' myself with that I'm a 27 year old with an imaginary friend...

So how do you do it? How do you get over the fear of rejection?
Do you try to understand it?
Do you just say it really fast;"doyouwannagoonadatewithmesometime?"
Do you try to talk yourself out of wanting someone?

Perhaps what it all boils down to isn't his wants or his response, or anything about him really. Maybe taking risks isn't about being at the mercy of someone else's opinion of you. Maybe it's just as simple as thinking enough of yourself to go after the things you want...