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Our guide to getting laid and finding love in Portland took inspiration from a perhaps-unlikely source: Ann Landers.
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Landers was the pen name of a Chicago Sun-Times advice columnist named Ruth Crowley, who started writing the column in 1943. When Crowley died in 1955, the Sun-Times held a national contest to find her replacement. A Chicago housewife named Esther Lederer submitted a set of sample columns that stood head and shoulders above the other submissions. That’s because rather than simply wing it, Lederer picked up the phone and asked some experts to help her untangle her readers’ problems. When I started work on the stories that follow, I decided we could do the same: pick up the phone (or, OK, open an email) and talk to some experts about how to navigate sex, dating and relationships in 2026.
It turns out one of the internet’s best-known relationship experts lives right here in Portland. If you’ve logged into TikTok or Instagram lately, you’ve probably seen a video by Therapy Jeff explaining concepts like the No. 1 predictor of long-term relationship success, or how to tell if your partner is (his words) a big turd. If you’ve ever wondered what’s behind those videos—and how he justifies using short-form video to explain something as complex as human relationships—we’ve got you covered.
Internet famous or not, we found plenty of other people who have things to teach us about modern love. We spoke to the lawyer who helped bring marriage equality to Oregon about how you can avoid calling him to handle your divorce. We also got the scoop on queer sex parties, rope play, and ways to meet someone new outside the apps. We also found a few places you can go once you’ve made a connection. And yes, one of our writers has been to every sex club in Portland—so she knows which one has the best buffet.
No one person featured in the following pages has all the answers, and honestly, that’s kind of the point. I hope you’ll find something here you can use—whether you’re looking for sex, love or something in between, or have been off the market for years but want to keep your relationship going strong. —Christen McCurdy, Interim Arts & Culture Editor
