I don't feel cool enough for this guy, help?

[Lois]

I went to school with this guy, he didn't seem interested in my in any kind of non-platonic way at all. It's been 6-7yrs now since I've seen him in person. We've been friends on Facebook. Seems we have a lot in common. He did a project and I like it, and he said he'd send me my own copy no charge, but proposed that I pay him back by buying him a beer. He didn't seem into me b4, n i wasn't the best in shape girl, and I've gained more weight since he last saw me, so I feel like there is no way in hell he'd be interested in me now- i feel embarrassed to meet up with him. He is rly cool. I sound like a dork now, but I really am just a dork. I guess I've always thought he is really hot, and awesome, but I'm just so self-conscious about him seeing me. Like if he saw me he'd immediately regret his proposal. He said to send him my addy to send me my copy. I feel like messaging him my addy would initiate the whole thing, and I feel so awkward that I'm totally chickening out. Am I being irrational here? If I'm feeling this self-conscious about it, is that a bad sign to begin with? Initiate sequence or ignore- that is the question. If you thought u connected w/ an old classmate, and met up with her n she was noticeably fatter, would you totally be turned off? Even worse~ what if i totally misread his proposal to buy him a beer? What if he did just mean it in a platonic way?

[Jo]

Good for you initiating this. You will never know if you don't put yourself out there. If he just sees you as a friend it's not the end of the world. The great thing about not being in high school anymore is that you don't have to see him everyday if it doesn't work out. You can forget it and move on. I'm sure you are a cool person in your own way; don't be so hard on yourself.

[Janet]

Relax.
Just go. And have fun.
If he's into you, you'll be able to tell.
If he's not, no big deal. It can still be a fun night.
If you worry too much about it, you'll make it awkward.
Relax.