Ooh, sorry about the not so pleasant life experiences, dude. And your friend gets the award for inappropriate use of an email.

Sordid is a pretty harsh word:

1. Filthy; dirty.
2. Mercenary.
3. Of degraded character; vile; base.

Ow, dude! I'm not sure she realizes how harsh a word it is. (I thought it sort of meant 'earthy'.)

You could shrug off her ridiculous comment, I mean, it's so stupid it's beyond offensiveness. I'm reluctant to burn bridges and to assume she couldn't empathize with your "mean experiences" is kind of a severe thing to say, too. Perhaps you could enlighten her, regarding her callousness? If she has a change of heart, you can decide whether it's worth salvaging the friendship. Most of us behave differently depending on whom we're hanging with. She can be your books 'n flowers girlfriend, because sometimes those simple people can be a drag. I don't see a problem with that.

But if she really can't deal with the new you, what she's offering is a friendship with strings attached. And if you can't be yourself in front of your friends, and this woman explicitly requests that you not be yourself in front of her, then what's the point? In that case, I wouldn't feel too bad about letting this proposal slide.

Shy people (including me) are too self-conscious. We're too wrapped up worrying over what kind of impression we're making, so we waste a lot of energy monitoring our actions and responses. (At least I'm guilty of this.) I can't give you a magic pill that will help you to easily overcome this mindset, but one thing that really grounds me is the revelation that it isn't all that important what other people think of me. If you try too hard to be friendly, it turns people off. The fact is, most people aren't thinking about you, anyway, and even if they don't like you, it's not the end of the world.

A really big part of getting over your shyness is changing the way you think. For example, don't put girls on pedestals. That makes them seem even more intimidating. Don't take yourself so seriously, and don't worry about making a fool of yourself. It's actually endearing to see a guy act a little dorky. Try not to get too keyed up. Girls want to hang out with guys who are comfortable with themselves.

It's difficult to approach someone if you don't have a plan. Try to come up with a few things you can talk about, before you say hello. Having something in common is always a great way to make a connection. There's no reason why you can't strike up a conversation with anyone in any of your classes. (Sure, easy for me to say, but I did ask to borrow the notes of a guy I had a major crush on.) It's even easier if you participate in the same after-school activities.

This site offers suggestions for things you can do now to overcome shyness with women (I can't vouch for how legit it is, but it's worth a shot) and this site has a few links you can explore regarding shyness, as well.

Good luck, Woggo! I know it's tough. Shyness is something I struggle with every day. But the more chances you take, the easier it gets.

Hugs and kisses,