The People You Date in Portland
Like Patton Oswalt once said, "Dating is like a really fun nightmare." That's especially true in Portland." Between the transplants, emotionally stunted quarter-life crisis specialists, techies, beer geeks, yoga freaks, and nomads, it’s a mosaic of romance that’s far too weird for a newly single person to be expected to successfully navigate on their own.
Be sure to study this list of the most common specimens in Portland’s meat market before venturing out in the wild on your lonesome. Print it out if you need to, because checking your phone on a date is still incredibly lame.
You meet Ashley and her dirt-twirler friends during a drum circle at Colonel Summers Park on Monday Funday. You know dating a wayward 21-year-old idealist who was probably working at a Hollister in Orange County two years prior is a terrible idea, but she cleans up well and doesn’t smell quite as weird as the band of Canadian drifters she’s been bopping around with since they picked her up at the Oregon Country Fair. She wears a lot of fresh new duds from Poler and Brixton, so it’s safe to assume she won’t be bumming cash any time soon.
Your first date: She loves taking pictures of sunsets, so a joint and a six-pack at Skidmore Bluffs is a guaranteed win. The two of you only get an hour of alone time before her friends materialize out a cloud of patchouli, dust, and #chillvibes. She leaves abruptly when she finds out a Couchsurfer her housemates are putting up fed her cat some edibles.
The inevitable breakup: She bails on plans to go camping one day and vanishes into thin air. Your friends never had the chance to meet her and you begin to wonder if she was even real to begin with. You swear the latest visualization reel Tycho uses on tour has slo-mo clips of her hula-hooping in the desert, but no one believes you.
It’s unclear what Trent does for money, but you’re pretty sure it has something to do with promotions or social media or an obscure Japanese vodka brand. He’ll never pick up the check, however, because he spends most of his cash on Teklife records and overpriced monochromatic athletic wear from Machus. He inexplicably has 15k Instagram followers.
Your first date: A trap night his friend is throwing at Holocene. You’re reluctant to meet a guy you met on Tinder at an event with “trap” in the title, but it turns out to be a blast despite giving you tinnitus and a terrible hangover.
The inevitable breakup: Frustrations mount as it’s rarely clear whether or not your meetups at the various clubs he “knows a guy” at are dates because his squad of dudes with topknots and man leggings is always around. He then disappears for a week, loses his phone, and hits you up a month later at 4am with a story about how a last-minute VIP ticket for What the Festival is the reason he ghosted.
The Salty Gen X-er
Neighborhood: Brooklyn/Lower Powell
Sick of dating bozos who still get excited about Mumford and Sons and the Joe Rogan podcast, you’re turned on by Cliff’s piss-and-vinegar attitude toward mainstream pop culture swill. He has a solid record collection that predates the mid-00’s vinyl resurgence, and he still makes you thoughtful mixtapes despite your lack of a tape deck. Cliff likes to spend the morning after sleeping in, chain-smoking, drinking black coffee, and listening to KBOO between bouts of hungover copulation -- a welcome respite from standing in line for brunch somewhere while wondering if it’s best to walk away from your mistakes now or after your chicken and waffles have been paid for.
Your first date: A dive bar you’ve never heard of in your neighborhood -- not his -- because chivalry is not dead. Also because he wants you to think he owns a car even though he’s really borrowing his ex-girlfriend’s Subaru for the weekend while he watches her cats.
The inevitable breakup: You admire Cliff’s forthrightness and his preference for actual phone calls over emotionally cryptic text chains, but the voicemails he leaves at 4am on weeknights are a bit much. He’s a sweet guy, but his job at Powell’s is going nowhere so you ghost him and hope he takes a hint. His final voicemail calls you out for using him as a “cultural accessory,” and you make a point to buy your books on Amazon for a few months.
The Spiritual Predator
You meet Dane in line at Whole Foods when he fumbles to present the reusable packaging for his various roots and herbs to the cashier in a timely fashion. He senses how stressed out his inconsiderate durdling is making you and invites you over to his “workspace” -- a cramped studio apartment off Sandy that reeks of curry -- for meditation and “guided release.” He believes he’s a walking conduit for “positive energy” and is certain the other people in his yoga class aren’t giving it their all because he’s the only one who openly passes gas.
Your first date: Smoothies at Prasad in The Pearl. He shows up wearing frayed harem pants and makes passive aggressive comments about the immoral clothing choices of the gaggle of young moms in Lululemon pants at the adjacent table.
The inevitable breakup: As much as you love Dane’s positive energy and his toned bod, it becomes obvious that his “heightened state of being” spiel is just a put-on to get girls to do butt stuff on the second date. You encounter him months later on the other side of the deli counter at New Seasons with his ponytail lopped off and a nametag that says “DAN.”
The Agency Douche
Neighborhood: The Pearl
Kyle is a man of many hats who’s always on the hustle. When he’s not starting boutique agencies with monosyllabic names that operate out of rehabbed warehouses and then ditching them a year later, he stays busy collecting sneakers, traveling to Asia, and uploading hot vaporwave remixes to Soundcloud. Kyle’s most prized possessions are his imported-from-Japan Subaru WRX STI and the signed photo of him and Drake that lives in his office atop a teetering pile of Fast Company back issues.
Your first date: Cocktails at Jacknife. His short attention span gets annoying, but you’re able to give his furtive texting a pass when a crew surrounding a member of the Portland Trailblazers walks by and invites both of you to join them for bottle service at a mysterious club in a basement somewhere. You wake up in his luxury apartment the next morning wondering if that helicopter ride you vaguely remember was a dream or not.
The inevitable breakup: Wondering who he’s interacting with on his phone all the time starts to get really old. You’re committed to dumping him during dinner at Imperial, but he gets kicked out for doing coke off his iPhone in the bathroom before drinks arrive.
You’re drawn to Chad’s youthful idealism and free-spirit vibes, and you’re willing to give his lone dreadlock with a seashell in it a pass because his Tinder profile says he lives on a boat. The kombucha cart he’s saving up to get started will donate 90% of its profits to the Tibetan independence movement, which is a pretty dope idea, right?
Your first date: A potluck picnic in Mt. Tabor Park. You get an uneasy feeling about the food you just ate when Chad rolls a post-meal fatty and tells you about his favorite dumpster-diving spots on 82nd.
The inevitable breakup: Chad’s an excellent bullshitter, but his burnout tendencies expose the trust-fund hippy lie that is his life rather quickly. It wasn’t the pursuit of a philosophy degree at Naropa that drew him to Boulder before landing in Portland -- it just so happened he was following Phish for a summer and somehow got left there. And that boat he lives on? Well, he does live on a boat, but it’s up on cinder blocks in his buddy Drew’s front yard in Lents, which is totally not Montavilla.
Brittany, age 29
Neighborhood: Vancouver, WA
Heeding your friends’ advice to stop being so picky with your Tinder swiping, you digress and start swiping right on those photos of seven completely identical shiny blonde girls in brand-new Seahawks jerseys. You have no idea what to say when you and Brittany match, but she goes hard out of the gate and has plans locked down in under five minutes. You wait until after numbers have been exchanged to read her profile, the bulk of which is an incoherent thread of emojis followed by a disclaimer about how she won’t date you unless you’re a non-smoker with a car, a job, and a place of your own. You keep scrolling and find a link to her very active Myspace page that sits where most girls’ Instagram handles would normally be.
Your first date: She doesn’t even flinch when you jokingly suggest the Hooters at Jantzen Beach as a logical halfway point between the two of you. You’re delighted to find out she happens to know half the wait staff on a first-name basis and can still manage to look cute while inhaling a mountain of wings and a gallon of cheap beer.
The inevitable breakup: You start to worry when she stops texting you bathroom selfies 30 times a day, so you take to the internet to do some recon. You find her other Instagram account and come across a photo of her smiling ear to ear because the tattooed, Affliction-wearing ex-marine boyfriend she has a kid with -- neither of which you had any clue about -- finally proposed to her. You block her number, tighten your search radius to “four blocks” and have a second deadbolt installed on your front door.
Neighborhood: St. John’s
Leitha is intimidating at first, but she eventually warms up when you’re able demonstrate a working knowledge of the Riot Grrrl movement beyond low-hanging fruit like Sleater-Kinney and Bikini Kill. Leitha is a sassy altruist at heart and spends most of her time volunteering at ClamBake -- the women’s rights infoshop/vegan bakery she founded with her roommates from Evergreen after they all moved to Portland together. You had no idea what sex-positive feminism was until you met her, but now you do and you’re pretty into it!
Your first date: A vegan powerviolence show at Black Water Bar. Leitha is quick to point out that the shuttering of Portland’s non-traditional music venues is a travesty of the highest order because not everyone in the scene can feel comfortable at a bar, but a few well whiskeys later you’re making passersby uncomfortable because you’re making out in the street.
The inevitable breakup: A friend back home sends you a link to a piece Leitha wrote for Jezebel titled “Inside and Within: The Plight of the Basic Northwestern Male.” You sheepishly invite her to coffee to “talk about some stuff,” but she’s already moved to Philadelphia and started a drummer-less punk band that got signed to Kill Rock Stars before they recorded a single note of music.
Brad quit his boring 9-5 in Southern California and moved Portland to get a foothold in the craft beer industry before it gets too corporate. He bitches constantly about “big beer” enveloping every last brewery with integrity, but he’s secretly hoping the Triple Black Imperial Pilsner he’s been brewing in his garage attracts a buyout so he never has to work another day in his life. Brad loves his PAX 2 vaporizer but absolutely detests stoner humor. Cannabis is artisanal craft, too, bro.
Your first date: Beers and burritos at Apex. Brad shows up in cargo shorts and chastises you for skimming the menu for a familiar IPA, noting the popular brew style “is basically Bud Light for hipsters now”. He puts down three vanilla mocha stouts while mansplaining IBU’s and initial gravity. A few beers later. he flips out on the bartender for their cash-only policy and tells her to expect a vitriolic post on his beer blog by the end of the day.
The inevitable breakup: You realize Brad is passing off his excessive lifestyle as “connoisseurship,” but you don’t want to hurt his feelings by telling him you’re genuinely worried he may get a case of gout. Luckily an opportunity to bail is gifted to you when you watch Mad Max: Fury Road together and he angrily agrees with the Men’s Rights Activism theory that the movie is really an explosion-packed trojan horse for The Feminist Agenda.
The Med Student
Neighborhood: South Waterfront
Carrie won’t hesitate to remind you that she got into better med programs in less interesting cities, but the sirens call of the mountains and the bearded boys and the gluten-free everything inspired her to pull an audible and redirect the Rav4 towards Portland. She’s made it very clear in her dating profile that school takes up 90% of her life, but she still has plenty of time to scour every dating platform available in search of that fictional jock-hunk-scientist-nerd who’s eagerly waiting to provide her with the Notebook romance she only has two hours a week to contribute to.
Your first date: Drinks at Sweet Hereafter. You notice she keeps ordering cider but try not to say anything about it because you know a long-winded science lesson about gluten is right around the corner. You make plans to go on a hike in The Gorge that weekend and your Instagram account is immediately inundated with her tagging you in every picture of a mountain she can find for the next four days.
The inevitable breakup: She ditches you when the only remotely attractive guy in her class finally dumps his girlfriend and makes a move. They couples match at the hospital of some Big Ten university and are never heard from again.
The Basic Beavertonian
Neighborhood: Raleigh Hills
With a condo, a solid Nike paycheck, and a deep respect for his overbearing mother who lives two miles away, Kev is everything your parents want you to desire in a partner. His bitchin’ tan and entry-level Mercedes make you wonder if settling for a decent guy who only left The Beav’ for a stint in Corvallis is the right choice after all those hirsute manchildren east of the Willamette left you broke and devastated.
Your first date: Sushi at Bamboo on 23rd. He’ll sneak the waiter his platinum AmEx before you’re even seated, but he’ll still pretend to care when you explain how not going Dutch on the first date is repressing feminism in some way or another. You both go hard with the Yamazaki and take an Uber back to his place. He mispronounces Bon Iver while he sets the mood on his high-end stereo system, but you’re too enamored with how tidy and lacking in vintage beer signs and motorcycle parts his place is to care.
The Inevitable Breakup: After a month straight of staying over and bingeing on Netflix docs and pricy Postmates deliveries, Kev settles and stops wearing anything besides black Nike workout gear. He invites you and “your crew” out to a night of barhopping on the east side to celebrate his former OSU frat brother’s engagement, and the frequency and sincerity with which they use the word “hipster” to describe everything from cocktails to sandwiches starts to weird you out. You insist he stay over at your place after constant tardiness due to Beaverton traffic hell almost costs you your job, but he resists by claiming he’s afraid of your roommate’s dog and all the black mold in your decrepit apartment.
Neighborhood: Alphabet District
Andrea is an upbeat self-starter who doesn’t believe in days off and uses the term “power lunch” unironically. After seeing her in meetings with middle-aged account executives every morning at your neighborhood coffee shop your paths finally cross at an Avett Brothers show at Edgefield. She tells you how much wine she’s had and you exchange numbers after making out in her Jetta for an hour.
Your first date: Happy hour at Rontoms. Andrea tells you how much she loves seeing hipsters in their natural habitat. She then smacks your hand before you take a bite of your hummus platter -- she needs to Instagram a photo of it for her food blog while it still looks so pretty! You ask her what she does besides food blogging, but she tells you about how liberating her divorce was and what you can do to really make your LinkedIn profile “pop” instead. You have no recollection of giving her a link to your LinkedIn profile.
The inevitable breakup: Andrea keeps dragging you to networking mixers that are full of people with their Twitter handles on their nametags. You find her insistence on giving you a made-up backstory of lofty career goals beyond playing in bands and bartending a bit offensive, and you begin to doubt the authenticity of her newfound Portland lifestyle when she won’t stop showing you Facebook photos of her former sorority sisters’ babies and suburban tract homes back in Indiana. You delete your LinkedIn profile and never look back.
The Deposed Brooklynite
Jess left a high-stress music PR gig in Williamsburg when her most high-profile client got torched by Jezebel and Lena Dunham for being a misogynist. She heard from her comedian friends that Portland is basically Brooklyn with trees, so she threw her few belongings in a Duane Reade bag and drifted west in search of cheaper rents and beardier men.
Your first date: A multimedia gallery opening at a fly-by-night event space in the Southeast Industrial District. You’re not sure whether you should be impressed or intimidated by how she knows every other person at this thing despite having only been here for a month. You spend most of the night deliberating whether or not it’s rude to ask her why she has a flip phone.
The inevitable breakup: You’re pretty sure Jess is going to leave you for the bassist of that band that just released a tape on Burger Records, but you decide not to stick around and find out when she replies to your texts with “Sorry lost my phone/numbers...who is this? ;)” for the fiftieth time.
The Dog Mom
Kelly is a sweetheart with strong maternal instincts and a refreshing lack of judgment and pretense. She playfully refers to her aging mutt Toby as her boyfriend, and there’s not a single place she goes without him in tow. You love dogs and were bummed out when your new apartment building’s stringent anti-pet policy made dog ownership an impossibility, so you’re all about #TobyTime and the million other hashtags she uses to document their adventures in the Pacific Northwest.
Your first date: A hike in Forest Park. She takes a selfie of the three of you near the overlook at Pittock Mansion and tags it #MyBoys. You see the photo in your feed later and realize you’ve been cropped out.
The inevitable breakup: You get tired of your dining options being limited to bars with dog-friendly patios and you keep getting asked to leave real restaurants that Kelly insists are pro-Toby. The final straw comes when Kelly gets up and leaves in the middle of intercourse when she can’t shake the feeling that she didn’t leave the TV on for Toby to watch while she’s away. You’re glad lint rollers and Beggin’ Strips are no longer line items on your monthly budget spreadsheet.
The Self-Aware Midwesterner
Like most transplants, Steve moved to Portland without any solid plans besides riding his bike everywhere and hopefully living in a bungalow with some dudes. He thinks his blue collar roots and superior Midwestern work ethic exempt him from being just another transient who moved here to do nothing, but until he puts that communications degree to work at a job that doesn’t involve asking people with real jobs if they want whipped cream on their mocha then he’s still part of the problem and not the solution.
Your first date: Happy hour at Aalto Lounge. He knows it’s an obvious choice for a first date spot, but he sells you on the fact that making fun of other people on awkward first dates is good cheap fun. You realize Steve is actually kind of a dick, but he’s funny and self-deprecating about it and you imagine him getting along well with both your boring friends who like football and the crew of neo-anarchists you met in grad school.
The inevitable breakup: Steve is good at finding crafty ways to explain how his existence as an underemployed service-industry lifer transcends the garden-variety manchild slackerdom that makes so many men in Portland undateable, but your conscience raises a red flag when you realize a month into the relationship that you can’t bear the idea of explaining him to your parents. You feel sorry for breaking up with him until he posts a link to a story he wrote about dating that involves a few characters that bear more than just a coincidental resemblance to your most obvious traits. You get engaged to the next guy you meet on OK Cupid within six months.
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Pete Cottell is a Portland-based writer who's eternally single and may or may not refer to himself as "Steve." Follow the outcome of his ill-advised romantic gestures at @Vanifestdestiny.