Dating Can Be A Struggle in Portland. What’s the Deal?

“I have dated in San Francisco, Seattle and Colorado, and… though there were bad dates, they were not even close to the garbage fire that is dating in Portland.” —Isabelle

It’s true, you could probably find hot takes like this written about any city — but even the experts agree that Portland’s dating scene is unusually tough to navigate.

The Great Love Debate podcast named Portland the fourth-worst place in America to find love last year, and countless Reddit users and OregonLive commenters have been saying the same thing for years.

So what’s the deal with Portland’s dating scene? Here’s what our sleuthing has turned up so far.

#1. It’s worse for some people than others  

Anecdotally speaking, the most frustrated group of singles appears to be single women in their 20s and 30s, who spoke out en masse when The O’s Lizzy Acker wrote about dating woes last November.

But other groups seem to be doing better. For example, straight men in their 20s hold some of the best statistical odds in the country of finding a date here, and LGBTQ-identifying singles in Portland also have an unusually high number of potential matches to choose from.

#2. Portland’s beer culture can go too far

When The Great Love Debate podcast ranked the worst cities in America to find love, it gave a pretty specific explanation for choosing Portland: “Trying to be the center of the Beard & Beer Universe is never a good way to show you actually care about dating.”

The complaint that men drink “way, way too much” in Portland was also cited by Acker, who shared this note from a single Portlander named “Brooke”:

“I’d argue that Portland is one of the worst places to date as a mid-twenties single,” Brooke wrote. “If you want to date someone outdoorsy, odds are he lives in a van and barely has a day job. But if you’re looking for someone with a steady career, he probably drinks away his Friday and Saturday nights and spends Sunday glued to the TV, obsessing over his fantasy football league.”

Ouch. 😬

#3. Expectations aren’t always aligned

For better or worse, dating can mean a lot of different things in Portland.

According to the dating site OkCupid, more than 15 percent of its Oregon users say they’re in the market for casual hookups ranking us #1 in the country.

Throw in the fact that Portland has a reputation for polyamory and kinkiness (we were named the “kinkiest city in America” just a few years ago), and it’s clear why people with more traditional expectations for a relationship might have trouble finding their match.

Portland is (or at least was) a place for misfits and weirdos,” sex educator Amory Jane told the Portland Mercury. “We’re more accepting of folks doing things outside the norm.”

#4. Portland has a passivity problem

You can call it PPMS — or Portland Passive Male Syndrome.

“Men are just really nonchalant and kind of loosey-goosey about plans, almost like they’re not interested,” Allie Fuller told OregonLive in 2011. “People will say, ‘Why do you think you’re single?'” And I’ll say, ‘Oh, you know, I suffer from PPMS.’”

The Merc’s “Dating State of the Union” in 2016 also pointed to flakiness as a quintessentially Portland problem. “A lot of folks don’t seem to know what they want—which is understandable,” Amory Jane said, “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.”

BarFly Magazine founder Jennifer Lane agrees: “I’m from New York, where people are a lot more direct about whatever they’re feeling,” she told OregonLive. “People here are so casual, sometimes it’s hard to tell if you’re actually on a date, or not.”

#5: Most singles aren’t great at “car shopping”

I called up dating rehabilitation specialist (and Bridgeliner reader) Kelly Marie Hoffman to get her take on Portland’s dating struggles, and she said the biggest problem she sees is that singles often don’t know exactly what they’re looking for.

Hoffman compares it to car shopping — if you know you’re looking for a red sportscar with great handling, you’re going to find the right match a lot faster than if you start test driving random cars in the lot.

She says it’s the same way with dating: The more you know about the qualities and traits you’re looking for in a person, the better your odds will be of finding love in any city.

“You have to stop thinking that the right person is just going to come along when the time is right,” she said. “That’s one in a million. You need to go looking for it.”

What’s your love story?

In the spirit of learning together, we’d love to know: How have you found love (or tried and failed) while living in Portland?

Send us a love story of 100 words or less, whether it’s triumphant or tragic, cringe-worthy or hilarious. We’ll pick a few of our favorites to share in the newsletter throughout the month. 💖