I have this...problem

Ok maybe y'all can help me out with this one, or refer me somewhere where I can get some good professional help. Here's the deal...

In normal circumstances, I consider myself a fairly outgoing and gregarious type of guy. I love people, and I thrive in social environments with good folks around me.
When it comes to men, I usually have no problem with being a huge flirt and asserting myself when approaching or being approached. I'm not even gonna lie and say that I got game because I have none whatsoever...i hope my easy going nature and optimism are game enough.

Here's the problem I'm having...When I'm dealing with somebody who's an "average joe" or someone I am certain is feeling me, I'm like a lion...i'll pounce in a second. Whereas, when I encounter somebody who is either unreasonably FINE, very accomplished, or highly intellectual (or a combination of all three), I FREEZE.

It's like the second I have an opportunity to act, I start getting all anxious and self-conscious. I break myself down to see if I can compare. Am I attractive enough? Am I smart enough? Is my wit quick enough? Am I experienced enough? (yes that's a concern of mine, being 25 and able to count the total number of sexual encounters, not partners, I've had on two hands and a foot) What qualities do I possess that might interest this guy? What could this amazing specimen of man desire in me?

This of course is crazy as hell because I know that I am a good catch, and I'm not some mud duck. But why is it that I can't shake these insecurites? This is starting to pose a problem now that my social environment is changing and I'm encountering more and more men that I would consider 'amazing specimens'.

For example, I came across a guy during my conference trip to San Diego a few weeks back. When I first saw him I was like DAMN! Tall, dark skinned (my absolute favorite mmm), well groomed, beautiful smile, easygoing personality, educated (in the same field as myself) the list goes on. Turns out we have a few mutual friends. After my weekend in SD and little bit of investigative reporting back at home, I find out that he is 'family', a nice guy, and available. So why haven't I attempted to holler and swoop down on ol' boy? The 'self-conscious' monster has gotten my ass and Mr. Fear of Rejection has me in a headlock. I have access to his e-mail address, blog page, and I'm sure my friend in San Diego wouldn't mind facilitating some sort of hook up. I have all this ammunition, and yet I sit here tearing myself down to the elements and unearthing my flaws as excuses to not try to establish contact.

So what do you think? Do I need professional help, or the assistance of a few strong cocktails?

Oh yeah, it doesn't help matters that I'm ridiculously sexually repressed right now and my loins feel like they're gonna self-combust at any minute. Just thought I'd add that in, :)

Comments, suggestions, and physician referrals are graciously desired.