Go get 'em!
Tracker_NPC,
If you want to attack your shyness, I recommend you enroll in some courses / activities that have a high female to male ratio, like dance lessons, cooking, yoga... something to be exposed to lots of females and slowly but surely you will gain confidence.
Also, I can recommend (even if it sounds blasphemous for a romantic kind of guy) that you sign up for a couple of speed-dating events. It's around $50 bucks and you'll get to talk to lots of girls. It's a little bit like seeing an SP in the sense that you pay for someone to allow you to be in contact with them on a somewhat "artificial" environment, but trust me, it will hone your social skills with the females.
Google "speed dating in Vancouver" and you'll get more than a few options.
If you're too shy and worried about being seen by someone familiar, you can go to an event that takes place in a different area than where you live or hang out.
I can tell you that it's a great exercise in shaking off that silly shyness that creeps up on you and takes control of your cool when you're trying to talk to a girl. You will probably come out of that event with a match (i.e.- phone number or email address) and with a better sense of what girls are looking for. You'd be amazed at how easy it is to spot a pattern in the "wants" and "needs" for the typical urban girl here.
Anyhow, I wish you all the very best, just be clear about what you want for your life and pursue that dream with passion. Don't focus too much on the goal, make your journey and your learning the main objective and reward. Don't see adversity as a sign of impending failure; view adversity as your opportunity for growth and self-improvement!
I came here out of necessity because the itch that I just couldn't scratch had gotten continually worse and worse; and my shyness had not gotten any better. I constantly told myself all the problems but after so many years of loneliness, I had begun to doubt everything that I was thinking. Dipitydoo (& a few others) have convinced me not to start off with an SP. And, actually, I am feeling alot better now that my conscience has been reinforced.
I'm going to try getting over myself and get out there alittle more... it's hard for me, but if I use this as incentive... there's a chance I could still make it (before I go completely nutty

).
Thanks so much everyone; Your comments and PMs are so well written and insightful. You have no idea how much internal grief you've saved me from. I really really mean it; thank you so much.