I am actually staying in Portlnd this week and next. It's great. Go Sam Adams! (Gay mayor to be next year)
I'd say it's very relaxed when it comes to LGBT. There doesn't seem to be a specific gay area like Castro in SF, Chelsea in NYC. But there are gay bars, community services, and etc.
They have lots of local organic food available. That's another thing I personally I like about.
However, a friend of mine who lives here is still single shouldn't mean anything.