These people represent a slice of the diverse sexualities and relationship statuses of our city.For all their differences, what they have in common is a sharp perspective on the assets and liabilities of dating in Portland.Unless something drastically changes by press time, I've been single for the entirety of my 26-year existence. I've never declared my relationship status on Facebook.I've never said "I love you" to a partner and meant it.Both of these people want to get brunch and day-drink on a Sunday. A lot of folks don't seem to know what they want—which is understandable, but when you mix that with the stereotype of Portlanders being flakes or passive aggressive in their communication...it's a combo that tends to lead to some confusion, annoyance, or heartache. I've noticed that a lot of folks don't really say what they want, or even know what they want beyond "being open to different sorts of connections." Jo Ann Schinderle, 29 Straight female Portland resident since 2012, last boyfriend circa 2006."If I had a dollar for every mandolin-playing barback I went out with, I'd have enough money to BUY MY OWN DINNER WHEN I GO OUT WITH THESE MANDOLIN-PLAYING BARBACKS." There's just not enough diversity in Portland—and I mean that in every sense of the word.
Each of their stories reminded me that when dating, it's best to be honest (with yourself and your potential partner), authentic, and remember that even if a date goes horribly wrong, you still walk away with a good story. Once got asked to go back to his place, smoke pot, and do "adult shit" on a date.I've found that dating is pretty relaxed around here most of the time, and I honestly feel like people are more themselves.Bri Pruett, 32 Straight, cis, female comedian, and former avid Portland dater, now in a relationship.I dated a dude from Boston for a spell, and he was horrified about my Portland dating experiences. "I recently realized I've never declared my love on any social media sites, so by Millennial Law—I made this up, but I think all millennials get my meaning—I've never actually dated anyone.But in Portland it's pretty easy to hook up with someone who is deeply invested in their macaroni necklace nonprofit startup woodworking poetry press." In Michigan, people get blackout drunk, and if they're lying next to someone in the morning, they try to date that person for a little while.Online dating brings singles together who may never otherwise meet.