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If you want to experience the ecstasy and agony of dating in Portland in 2023, Rose City Coffee Co. is a good place to start.
Located a few blocks south of the Aladdin Theater, the sprawling coffee shop hosts several speed-dating events each month, serving as a human merry-go-round for singles who chat in 10-minute increments, texting M for “match” if they’re into the other person.
Then comes 24 hours of waiting to see if the event produced any mutual matches. Finding out you were successful leaves you feeling desired, exhilarated and sometimes surprised. Finding out that you weren’t? Let’s just say that the doldrums of dating apps look pretty delightful when you’ve been rejected by a whole roomful of people.
If you think that’s an overly pessimistic welcome to our Dating Issue…well, you’re probably in a relationship. Out here, it’s bleak, my friend. Being single was already challenging before 2020, the halcyon age when we worried “only” about cyberstalking, fake profiles or being ghosted. And then what happened? Oh yeah: a global pandemic.
COVID-19 first made in-person dating an impossibility, then an improbability. As more and more workplaces have shifted to hybrid and remote schedules, singles have been asking where the heck they’re supposed to meet people. Blind dates are out of style, apps often lead to dead ends, and bar flirtations become a minefield when much of Gen Z perceives How I Met Your Mother’s “Have you met Ted?” game as a form of sexual harassment.
WW can’t solve the dating crisis any more than a right-wing columnist can convince college students to get hitched and move to the ‘burbs. But we do have perspectives and advice that might make dating these days less daunting.
Maybe you want more romantic partners? We break down the basics of polyamory. Want less turbulence in your love life? We examined whether the resurgence in matchmaking might do the trick. Plus, playwright Mikki Gillette interviews nine trans Portlanders about their dating stories, and we hear from Joe Gydosh and Michelle Sky, who founded the speed-dating service Luvvly out of frustration with apps like Tinder (and now host those white-knuckle coffee klatches in the Brooklyn neighborhood). Once you’ve decided on your dating strategy, we’ll remove another anxiety by giving you six perfect first-date spots to take your new sweetie.
Above all, we’re telling you: Keep your chin up. As you search for the one (or multiple ones), it’s easy to get discouraged. But new rules and methods haven’t changed the purpose of dating: connection with another person. That’s the reason we keep dating and the purpose of this guide. In the timeless words of Daniel Johnson, only if you’re looking will love find you. —Bennett Campbell Ferguson, Assistant Arts & Culture Editor
Willamette Week’s Dating Guide!
A Beginner’s Guide to Polyamory
Is Matchmaking Really the Answer?
Nine Trans Portlanders Share Their Dating Experiences