I took a flirting class once. I mean I really did. It was quite valuable, I learned all manner of helpful things. The class wasn't about how to get laid, it wasn't even just about finding romantic relationships. Lots of people flirt just to make everyone's lives more enjoyable.
Here is one hint from the class, although maybe it's not so applicable: the instructor said we should carry around business cards, when we meet a woman we'd like to get to know, write our cell number on it. Having a business card lets a woman know you have a job.
If you don't really have a job, you can get cheap business cards if you design them yourself.
And sorry we’re not in Portland yet! Our service is live in 4 cities right now (NYC, SF, Boston and LA) which is why the contest is offered there, as we have a large membership base to match members there.
I have a special challenge for you.
I'm the guy who wrote "Living with Schizoaffective Disorder":
http://www.warplife.com/mdc/books/schizoaffective-disorder/
For quite a long time I was quite certain I would never find love, as a result of my mental illness. Actually that turned out not to be the case, many women are completely cool with it.