I think that you should go for it Spoo. Like you said yourself, it is something that will help you feel better about yourself and that's is what is important. I think that people will overlook the braces, because you are so much more than orthodonthic work, I mean you're one of a kind poo flinging purple monkey. I'll even make a trip north in my school girl outfit while you are wearing those braces and we can make out in the backseat of a car! I might let you get to second base
Seriously, I understand where you are coming from - James have very much the same situation. He needed some dental work and it truly affected how he felt about himself to the point where he wouldn't smile. You've met James - that's a scary thing LOL. I forced the issue, because even though I loved him no matter what, he really let it affect him. Long story short, he got the work done, and now he smiles and you can see the complete turn around in his self confidence. Do it Spoo, you won't regret it.
Jenn