The first time I met my lady that I'm "with" now, I thought she was way out of my league... and she probably is. But had it not been for our mutual friends I probably never would have ended up talking to her. Like you said confidence is key. Once the conversation/flirtation was started I was in my element and whatever bit of charm I posess won her over. That was 4 years ago and despite many many roadblocks and often a few states distance, I've managed to hold on to her.
Score for the underdogs