Unless something drastically changes by press time, I've been single for the entirety of my 26-year existence.

I've never lived with a person I was dating. I've never declared my relationship status on Facebook. I've never said "I love you" to a partner and meant it. So, as far as dating is concerned, I'm about one step away from taking engagement photos with a burrito and calling it good.

When I moved to Portland last February, I was convinced that was all about to change. This would be the time and place in my life when I could date freely and successfully. Carpe diem, OkCupid! Here I come!

But with my new city came new problems. My high hopes and daily bus-ride marriage fantasies were quickly dashed by off-the-market married men, noncommittal fuckbois, and my own overwhelming lack of ambition. (Is it my fault burritos are so much easier to talk to?) Now I find myself back at the crux of perpetual singledom. I've finally started to wonder if it's because my life is some sort of Never Been Kissed parody or if the fault lies with the city itself. Maybe Portland isn't the dating mecca I dreamed it would be.

In an attempt to find out, I surveyed a wide variety of Portland friends, coworkers, comedians, and storytellers. 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.

Even after all these interviews, I'm still not entirely sure how I feel about Portland dating. It depends on my mood, and the level of my hope for humanity—which typically decreases with the number of times I've swiped Tinder that day. What I did learn from these generous interviewees is that I'm not alone in wading through the awkward Portland dating pool. 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.


Zak Toscani, 30

Straight male comedian, Portland resident since 2010 B.C. (before condos), mostly single since arrival. Once got asked to go back to his place, smoke pot, and do "adult shit" on a date.

My general thought on dating in Portland is that it's a hell of a lot easier than it was in Cincinnati. There are infinitely more people around my age in this town—so that alone opens up a lot of possibilities. 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. "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. Dating in bigger cities is different: There are more races, religions, and guys with jobs in finance. I dated a dude from Boston for a spell, and he was horrified about my Portland dating experiences. He also couldn't believe I own a hula-hoop. (So maybe I'm part of the problem?)

Suzette Smith, 33

Cis woman, eight years in Portland, single most of them. "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. Or they call them a slut and talk massive amounts of shit about them. Michigan is very sexually conservative, and it makes people unhappy. Portland people get blackout drunk and in the morning they're like, "Do you want to get brunch and day-drink?"

Portland hetero gender norms are also woefully conventional. There are a lot of cute guys in Portland, but they all have beards. It takes me a long time to trust someone with a beard. What's your face like, homes? The cute women have tattoos and their homes have extensive dioramas that you aren't allowed to touch. Both of these people want to get brunch and day-drink on a Sunday.

IMO, West Coast people are better lovers. Do they teach cunnilingus in school here? Because it's nice.

Amory Jane, 31

Female, pansexual, polyamorous. In Portland for 10 years, only single for a few months, but has dated extensively as a polyamorous married person. Teaches classes at She Bop (sheboptheshop.com), including one on non-monogamous relationships.

Dating in Portland has been a fun but sometimes frustrating experience. 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. If you know what you want, you will stand out! 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."


JoAnn Schinderle, 29

Straight female Portland resident since 2012, last boyfriend circa 2006. Co-host of the Portland dating podcast It's Not Me; It's Me.

I moved here for a job directing art shows in Portland and Seattle. I knew no one and was completely comfortable going out to events on my own. I noticed that in this town, girls would approach and hit on me 100 percent more than men would. When I brought this up to a then-new friend he said, "Oh, duh. I've lived here my entire life and this is the Northwest way! When a girl walks into a bar, every man notices her, but then they all look around to see the other men who also notice her. If one of those dudes walks up to hit on her, every other guy in the bar chuckles to their friends and says, "Ha! Look at this chump. She's not going to say yes."

THIS IS SO INSANE TO ME. A bunch of full-of-themselves sadboys would rather sit with their bros than make a move to meet someone? Meanwhile, the ladies in this town are movers and shakers in all facets.

Jay Flewelling, 31

Gay male, Portland native, long-term single person. "I'm really bad at being romantic, and definitely not the person to give advice on how to be Rico Suave."

I feel like I hear women complain about dating in Portland incessantly. They complain about how the "Portland Man" will never ask them out, never approach them, and if you want to date them YOU have to ask them—as if this a giant cross to bear. Guess what, ladies? People here don't care about gender roles of heteronormativity, and just like the gay world, there is no script for Portland dating.


Sarah Mirk, 29

Straight, cis, female. Single, but dating a few different people. Online editor of Bitch, media host of the podcast Popaganda. Author of Sex from Scratch: Making Your Own Relationship Rules.

One of the biggest things I learned writing Sex from Scratch is to be more honest. It's extremely difficult. But if you never respond to someone's texts, you're going to end up seeing them at New Seasons four times that month, and then you'll have to hide in the bulk aisle. You could just be straight up about it and say, "You're great, but I don't want to go on more dates with you. See you in the bulk aisle."

Zak Toscani: There's one girl who lives really close to me, and every time I see her I believe in marriage again. Anytime we stop and talk, I feel 100 percent better about myself. And I know it sounds corny as fuck, but I feel warmer just by being near her.

We went on a few dates, but our first date is my all-time favorite date. We walked around neighborhoods in Northeast. But she's kind of flaky, and ultimately I always felt like I was the only one pushing to hang out again. So every few months or so, I see her. We talk, I feel those feelings, take a shot and text her, we make plans, but something comes up and she can't make it. I've lived that loop a few times over.

There was actually one kind of cool resolution moment though. I was walking to get lunch and passed by her place. She was outside having a yard sale. We exchanged some banter and when I told her I was going to get food, she asked me to come up to her place for a bagel—and I told her, "I need more than that." In my mind I wasn't just talking about a bagel. That moment felt very "movie moment," like a scene from an early Bruce Willis romcom. I don't think she caught all that.

Megan Burbank, 28

Cisgender female, primarily straight, in Portland a year and a half, single about six months. "I have been on 1000 percent more dates with guys who are into Burning Man since living in Portland than anywhere else. Not my scene, but I like the enthusiasm."

My biggest complaint about the Portland dating pool is that it's small. Like, if you hook up with anyone, you WILL see them again. While you're out running errands. And it will be awkward. When I first started dating again after the end of a long-term relationship, one of my friends warned me about this, and she was so right. I'm warning you, too.

  • Kinoko Evans


Barbara Holm, 28

Female, non-identifying, four-year Portland resident, single. Co-host of the Portland dating podcast It's Not Me; It's Me. "All my friends are geniuses and I'm okay at masturbating, so don't worry about me."

Use the internet! That way you won't end up with some gun-loving weirdo. But also, just because someone has a 99 percent compatibility with you online, it doesn't mean they'll laugh at your brilliantly stupid puns, or support your desire to enact guerrilla-style sketch comedy in the middle of the street with strangers.

Megan Burbank: Online dating doesn't do it for me. Or it hasn't yet, anyway. I have been on one Tinder date, ever, and it was so fucking boring that I haven't done it since. It felt sort of like being kidnapped. You know things are bad when you find yourself fake-laughing at a guy's unfunny joke, while remembering Amy Poehler's advice to teenage girls not to laugh at a boy's joke if it isn't funny, and then realizing the reach of internalized patriarchy (it's in you!), and then having said dude ask you to weigh in on his idea for an app, and you're like, "Oh, sorry, I was just thinking about systemic oppression, maybe this was not such a good idea, gotta go, it's a school night, bye."

I think if you're going to online date in Portland, you should be pretty direct about what you want in your profile. I think mine says something really dickish like, "If you use LOL as punctuation or enjoy sending shirtless mirror selfies, save us both the trouble." Mean! But I get a much more self-selecting pool of applicants.

Bri Pruett: IRL meet-ups are my typical MO, because this is such a small town. You probably have a long-term Portland crush: someone you see everywhere, you run in similar circles, you see each other at parties. You follow each other on IG and Twitter, and you pay attention when it looks like they're seeing someone. A little dance I like to call: The Social Media Long Game. Or SMLG. It's a good way to find something that sticks.

Jay Flewelling: I liked online dating for many years in the sense of starting off with many questions answered that can never be known in real life. Such as, I know this dude is gay, his age, and a little bit about his interests. But I recently deleted my OkStupid account entirely. Now that I don't have that crutch, I find myself being pushed to make moves in real life when I wouldn't normally. That was the discovery, whereas before I would notice someone and NOT make a move, even if it was just saying "hi," because I'd think I'd just roll through profiles on my phone later. No thanks! I want to meet a real person in real life. I am a part of NetRippers, a LGBT soccer association that puts queer soccer teams together. I'm out there playing soccer with eligible bachelors because (a) I want to meet real people, and (b) I'm being scouted by the Timbers.

Sarah Mirk: I just joined Tinder for the first time two weeks ago, because I'm super busy these days, and not looking for a long-term boyfriend or relationship. I want to date around and have a good time, and Tinder seems like a good place for that.

I've had positive experiences with the app. I've also heard a lot of horror stories, but none of that happened to me. I wasn't inundated with dick pics. I've had good conversations about books, technology, gender, and dating in Portland over messages.

Tinder feels very public—and that's good and bad. I didn't get on it for a long time because I'm a private person, and it felt like raising a flag to say, "I'm single, I'm dating." In a bigger city you might be more anonymous. Portland feels like a small town. If you're on Tinder, people are going to tell your coworkers and friends, or people are going to run into you on the street and say, "I know you from Tinder."

But dating around shouldn't be embarrassing. I had to ask myself, "Am I ashamed that I'm single or that I'm dating?" There's a stigma there and it ties into our expectations for relationships. A "successful" person is in a long-term monogamous relationship, and that's screwed up in a lot of ways. Society instills a lot of shame around dating.


Jason Williams, 35

Straight male, five-year Portland resident, currently single. Author of Swipe Right: The Gentleman's Guide to Tinder Domination (or just Swipe Right) (swiperighttinder.com) under the penname Will Rockwell.

My dating advice for guys on Tinder would be stop trying to "hook up." Stop having an agenda, period. It's a silly app. Just keep it light, have fun, and get her number so you can meet in person to see if you two click.

If you're TRYING to get laid, you WON'T get laid.


Amory Jane: I think, for the most part, Portlanders are more open-minded about polyamory and monogamish relationships than other places in this country. I think it's because of the more progressive views here, and that Portland is (or at least was) a place for misfits and weirdos. We're more accepting of folks doing things outside the norm.

To learn more, I'd recommend doing some learning/reading about ethical non-monogamy. We have classes on open relationships at She Bop, and that can be a great place to start. Also,

More Than Two (the blog and/or the book) is awesome for people wanting to know more about polyamory specifically. I also would recommend doing some soul-searching and trying to figure out what you truly want. If it doesn't feel like a good fit for you, don't have an open relationship just because other people are doing it. If you don't know whether it is for you or not, keep an open mind, talk to other non-monogamous people for support, and take things slowly! Letting someone down or feeling disappointed that your relationship styles don't match is better than getting really invested and breaking hearts or homes. 

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