A FEW WEEKS AGO, the Mercury published a collection of advice and observations from some of Portland's most experienced and hilarious dating experts—a smorgasbord of dating questions asked, and answered ["Dating State of the Union," Feature, April 6]. We quickly realized that the story didn't end after reminding you that it's hard to avoid an ex in the bulk aisle of Whole Foods. You had dating stories to tell, Portland. And they are terrifying, true tales from the crypt.

In solidarity, I collected real-life dating stories from our panel of romance experts, as well as the Mercury's Portland Dating Dispatch blog, where anonymous locals stopped being polite and started getting real about seeking relationships and sex in Portland.

What did we learn? There's not much hope for us, fellow singles of Portland. Certainly, many of the shady characters from these tales still roam the OkCupid underworld, SO BEWARE! But reading these stories did give us a joyous taste of schadenfreude, an undoing of the fantasy-filled tropes of romantic comedy. We're not alone in our dating battles, Portland! We've all had bad dates, or caused them. But sometimes, just sometimes, all the trouble is worth it.


"Met up with a dude off of OkCupid. He showed up wearing house slippers and sweatpants because he'd been 'day drinking to get rid of his hangover.' (It was 10 pm when we met). He told me he was still hungover from an OKC date he had the night before. When I asked if he wore condoms, he said aggressively, 'What? No. I'm 34 and never wear condoms—I'm clean. I mean, I probably have HPV, but I dunno, men can't get tested for that shit.'

"He paid for my drinks and I ordered him a Lyft home from his phone." —JoAnn Schinderle, dating podcast co-host

"I met my former boyfriend Carl on Valentine's Day, and we went to a bicycle battle royale where someone started a food fight. I got hit in the face with a slice of moldy pizza from a dumpster, and he helped me clean the grease off my face. I just thought, 'Wow, he's so sweet.'"—Sarah Mirk, author of Sex from Scratch: Making Your Own Relationship Rules

"Some of my most interesting dating memories are from when my spouse and I were fairly new to polyamory. We went on a date with a triad (three people in a polyamorous relationship together), and it went so well that we continued to date them for a few months. This means that, at minimum, we were going out on five-person dates. Sometimes our dates would be six or seven people, since I had another partner at that time and so did someone in the triad. I'm sure most people would just assume we were any regular group of friends, until they watched us carefully and saw a lot of affection between everyone. We were basically a big blob of poly love, but it was not sustainable."—Amory Jane, sex class instructor at She Bop

"Blind date setup on OkCupid: Turned out he worked with a friend of a friend. He insisted on choosing the restaurant, and that he was going to pay. He chose the Woodsman = fucking expensive. Looking over the menu, I commented on the foie gras, saying I'd recently just tried it and it was good. The waiter came and my date brazenly ordered foie gras. 'Do you want the appetizer or the plate?' the waiter asked. He confidently ordered the $30 plate. I just ordered a burger to save money for this dude. The date went horribly. He baited me into an argument/discussion about being a gay Christian, which I quickly discovered, he was. I was trying to be polite about how I don't understand how a self-respecting gay person could also be a Christian (????), but he wouldn't let it go. He ended up boxing me into a corner, forcing me to admit that I think religious people are unintelligent. The food came. He's enjoying the dish, and about halfway through, he finally broke down and asked what foie gras was. I told him. He pushed the plate away and went to the bathroom."—Jay Flewelling, comedian, gay man

"Once I went on a random online date with a really hot guy who described himself as 'musical' and 'altruistic' and didn't at all mention that he was pretty severely mentally ill, un-medicated, and homeless. And sadly, he was hotter in person."—Bri Pruett, comedian, straight lady


"So I'm on SE Hawthorne, enjoying an early evening. A cute guy is sitting on a bus bench. He nods, gives the 'What's up?' line. I stop and we chitchat. He's pretty cute, and we start having an intense convo. Love, life, freedom—all in a span of five minutes. We're hitting it off! We come to the epiphany that in this world, you gotta not care what people think in order to make it. He proclaims, 'I don't care what people think!' and stands up, puts his hand down the back of his pants, and starts to dig around. I watch, horrified, as he pulls out a hand full of shit, walks over to the Hawthorne Theatre, and smears it down the side. Then I realize he's tripping balls! Without further comment, I stand up and walk really fast across the street. I hear him yelling, 'Piglet! Piglet! Oh, my piglet, come back!' He then starts walking after me. I run into the grocery store and tell customer service. They actually lock the sliding doors to keep him out, and I leave after a half hour.—Anonymous

"The next time you feel bad about your life choices, consider that one time I took a girl on a date to an arcade... where she gently reminded me that she was epileptic."—Anonymous

"So in LOVE. I mean real LOVE! Like the kind you feel way down deep, and you know everything is right in the universe, and is perfectly aligned. Time and space are totally on your side. You have found the one. You are the one. OMG, love is real! But then they're like, 'I totally care about you, I just need to fuck other people, and you're not invited.'"—Anonymous

"Okay, so I've never had good luck in love. Not for lack of trying, though. One day in '08 (pre-app era), I tried internet dating. I found someone, and took her to Montage. Things are good. Conversation is flowing, she's laughing, I'm charming. Then, before the entrĂ©e shows up, guess who walks in the front door? The ex-boyfriend. No, you can't make this stuff up, and no, it's not what you think. It's far worse. He didn't fight me, or even acknowledge my presence. Done guessing what happened? The guy proposed right then and there. The downside of a communal dining restaurant is that you have no privacy, making awkward situations worse. The applause was deafening. Me? I'm just embarrassed—and angry that I had already paid for the meal!"—Anonymous

"I met a man on some gay chat app. He was handsome and seemed nice, so we agreed to meet. We had several dates and one night he ended up staying over, and we cuddled by the fire. The next morning, I dropped him at home and he said he would call me later. Days passed and I called him to check in. Weeks passed, and his voicemail box was full. Two weeks later I get a mysterious phone call asking me lots of questions about myself, as well as confirming information. I ask who the hell it is and what's it about. I was then informed it was the lawyer of said disappearing date, and that disappearing date had been in a halfway house and didn't make curfew, and as a result had been sent back to federal prison. I was then told that disappearing date had stated I was the only person he knew in the area that he could remain sober around, and as a result could he be remanded to my custody until said date could be deposited in a drug treatment center on Monday due to parole violation. I picked up said date downtown at the federal prison—still in prison uniform—and then proceeded to take him to a family reunion campout for the weekend until he could be dropped off at the treatment center on Monday morning at 8 am. I still have a copy of his file from court with all the charges and evidence and photos, just to remind myself of said fucked date."—Anonymous

"We met at a bar and I immediately realized I wasn't into you. You were pretty enough, but I don't really go for the female 'jock' type. Regardless, we barhopped for an hour or two, talking about mundane things and consuming more alcohol. Then, my friend texted to say that another friend was playing at a well-known venue on Hawthorne. I suggested we go, so we went.

"Upon arrival, the booze must have really kicked in, because you became sloppy. Your words slurred and you didn't so much walk as wobble into the bar. I introduced you to my friends, and you had a crooked smile on your face while slurring. 'How's the food here?'

"We sat at a booth and you ordered a burrito, which I thought was an odd choice for a first date. The burrito came and it was massive—your eyes widened with joy. As you soaked up the booze with bite after massive bite, you grew quieter until it seemed as if you and the burrito were the only ones in the bar. You shoved that damn thing so hard into your face that it seriously grossed me out.

"Shortly after your meal, we left and I drove you home. We parked in front of your apartment. I left my lights on as a hint, but felt you were anticipating a goodnight kiss, if not more. The smell of garlic and beans from your burrito breath filled my car, and I, not wanting to be too rude, said I had a 'nice time' and wished you goodnight. You reluctantly left.

"The smell of that burrito didn't leave my car for three days."—Anonymous

Andrea Tsurumi

"One of my cooler friends—a lady about 10 years older than myself—wanted to set me up with a guy from her Taekwondo dojo. I was into it. She was a good friend who knew my personality, plus? Free dinner. I wanted to keep it friendly/casual, so I suggested she join us. In retrospect that's weird, BUT I'm also glad I did. Fondue dinners, I did not know, are three-hour affairs with a fruit course, cheese course, vegetable course, meat course, and dessert. Many little pots of warmed sauce arrived and perished. The guy turned out to speak entirely in Simpsons quotes, even when posed with direct questions about himself.

"What was the year you were born? 'You don't make friends with salad.' Where were you on the night of October 22? 'You'll have to speak up. I'm only wearing a towel.' Hoo boy. Can you imagine Simpsons-quote pillow talk? Stupid sexy Flanders."—Anonymous

"A few years ago I got set up with a guy. We went on a super uncomfortable dinner date to Mother's downtown. Upon entering I learned HIS mother had purchased him a gift card specifically for the occasion, and had called ahead to make sure the payment was worked out in advance. It didn't improve from there—when I asked what kind of music he liked, he looked really forlorn before telling me, 'some reggae.' That was enough. I didn't date again until meeting my current partner, over a year later."—Anonymous

"We met at Tugboat and hit it off instantly, racing through the conversation because we were so excited about what the other person was going to say next. She dragged me to a bar, another bar, her friend's drag show, a food cart, another bar, and finally back to her car where, quite drunk, she rifled through her purse looking for her car keys. 'Where are my fucking keys?' she yelled. Then she turned to me. 'YOU fucking took them! This was your plan along! You fucking...' — she started hitting me with her purse —'asshole!'

"After a face-heavy Gucci-sponsored smackdown, I ran to a nearby taqueria and ordered a burrito. Five minutes later she found me and pressed her face against the window, mouthing, 'I'm sorry' and making a kissy face. A waiter turned to me and asked. 'Bad date?' I just looked at him."—Anonymous

"I met a guy on OKC and we dated for a while. At first he said he lived in Portland, but actually lived north of Vancouver, WA. Small lie... but he was nice, albeit strange. Then he started to go crazy: talking about the barrel of a gun looking mighty tasty, questioning the loyalty of his family. Then he went bat-shit crazy!!! He was against circumcision, and anyone who disagreed with him was a rapist. He would go on tirades about how he was raped as a child because he was circumcised, and how he wanted to 'actively restore' his foreskin. He also claimed that male circumcision is the same thing as female genital mutilation—and it is NOT!!! He also claimed he could remember his circumcision and was 'emotionally traumatized' by it.

"When we broke up he took to Facebook to rant his aggression, and told everyone he 'got dumped' because of his stern beliefs. Then he sent me a message stating that if I am soooo pro-circumcision (as in 'not anti,' so therefore 'pro'), then I should have no problem cutting my lips off if I didn't want to brush my teeth, or that I should cut my ears off if I didn't want to wash behind them, blah blah blah. Crazy."—Anonymous

"Went out with a guy upon first moving to Portland via Tinder. We had a nice time out at a bar on SE Powell, drinks and a few Big Buck Hunter video games. Once some casual flirting and a kiss happened, it was time for me to go. That night I'd decided to take Car2Go, so he offers to walk me to my closest booked vehicle. As I fumbled through my bag for the single large key, we simultaneously (and awkwardly) kissed goodnight. This last kiss was not initiated by me, and kinda took me by surprise. Mid-kiss, I feel him GRAB MY CROTCH. Not in a romantic way, but like a cold hard grab. I quickly scanned the key on the window, got into my Car2Go, and drove away in a mixed combination of fear, anger, and regret for not punching him in the face."—Anonymous

Andrea Tsurumi

"I met you on OkCupid. You were cute, nerdy, and I was fresh out of a long-term relationship. You told me you thought it was hot that I was a female chef. When you picked me up, there were about 50 empty McDonald's bags in the backseat. We got stoned and talked about favorite foods. You admitted you'd never had soup before. When asked how this was possible at the age of 28, you said, 'I guess I always opted for salad?' so we went to Fubonn and I got all the ingredients to make you tom kha kai at home. You loved it. I invited you to my restaurant the next day. I said I would make you whatever you wanted. How about a fresh oyster po'boy? You said you would just take whatever soup was on the menu. That night, we mess around. Mid-kissing you try to jerk off. I blow you... and you tried to jerk off. We have sex... and you push me aside and start jerking off. I then realized there was far more disappointing issues to be discovered than your lack of culinary prowess. Hope you liked the soup."—Anonymous

"I went on a perfectly enjoyable date last night. With a guy who was interesting, employed, and cute. I actually felt more attracted to him (rather than repulsed by him) by the end of the date. We are going to see each other again this weekend. Maybe there is hope after all!"—Anonymous


We want to hear your Portland dating stories—good, bad, and ugly! Go to portlandmercury.com/portland-dating-dispatch to submit your true ANONYMOUS dating story on our new blog "PORTLAND DATING DISPATCH." And guess what? Our favorite submissions will be published weekly in the Portland Mercury!