If love is a battlefield, the war is being waged online. Since online dating brings a fair share of complications to the search for love, we asked Mercury readers to submit their weirdest, wildest true stories of their experiences looking for romance on the internet. And we promised the best story would receive a $300 prize! (You can read that winning story at the end of this feature, and more horrifyingly hilarious tales of love—where else?—in the online version of this story.) Enjoy... and, as these writers warn us, beware!


It was the “Wild West” of 2013. I was 23, a super-hot babe. I seldomly used OkCupid but found a cute guy. He had spiky brown hair and glasses. He was thin, but kind of built. I’m a towering 5’9” and thicc (with two Cs), so I’m not intimidated easily.

This person, who we’ll call “Brian,” had strong “Brian” energy. He came to meet me but lived in Salem. We met up at a cute little English-themed bar in NE Portland (you know the one).

He was smart and fun. I was not a prudish person then or now, so I didn’t think it was a good idea to have a person over on the first night. We each had about three drinks over the course of three hours. I had a Scotch egg. He was charming. He invited himself over for a beer, and I wanted a ride home... so I relented. While on my sofa he revealed that he was definitely too tired and tipsy to drive to Salem.

So this man... this scrawny little dork who could have been a stand in for Buffy’s friend Xander... was in my living room, conning me into sleeping over.

I was young. I was naive. I didn’t want to hear the next day about a mashed-up skinny guy on I-5.

I said it was fine, I had a full-size bed.

I woke up at 2 or 3 am to find him sleepily taking care of himself. Or to put a finer point on it, he was whacking off next to me.

So I stood up, went to the bathroom, and gathered the courage to ask him to please leave. Dear readers: When I returned, the man was pretending to SLEEP. I stood next to the bed, shoved him, and said “Brian, I think it’s time for you to go. I know that wasn’t an aggressive itch. I have three boy roommates. Goodbye.”

He looked at me, dejected, and got dressed. I walked him out, locked the door, and heard a single solitary “BITCH” through the open window on the porch.

Two years later, at a crisp and young 25, I got a random Facebook message request: It was our friend Brian. He said “It’s so weird, Facebook said I might know you, but we have no people in common. Lol anyway.”

I responded, “It’s so weird to jerk off next to someone you just met then forget them entirely. LOL!”

He apologized (insincerely) and deleted his message.

The one and only OkCupid date I’ve taken. —Anonymous


I met a cute, sarcastic redhead on Tinder. On our second date, he suggested we watch a movie. When I got to his place, his living room was full of workout equipment and woodworking tools. (Okay, whatever.) Then he showed me his bedroom: a plastic sheet hung in the doorway and THERE WAS NO BED—just planks of wood, saws, drills, and more woodworking equipment. CREEPY! I weakly joked about it being “very serial-killer-esque.” I did not get laid, but I made it out alive, so... silver lining?—Anonymous


I’ve been on a lot of online dates, but there’s one conversation I found particularly enlightening. I was visiting a friend in California and matched with a guy online. It never got to the date stage, but I sure did find our chat entertaining. Here’s what was said:

Him: I’ve been learning to day trade. So I’m looking to be in a relationship with a woman who can invest in me so I can take classes to become a better day trader and invest in myself and my account.

Me: Soooo... bet my kids’ college funds on you?

Him: I’m looking for an allowance. I’m not asking you to invest in my day trading account. I would never use someone else’s money to trade. I’m asking for an allowance that I can use toward classes. I’ll use my own money to trade.

Me: What’s in it for me?

Him: Well, I’d be open to traveling with you and starting a relationship together. So instead of random guys and random sex, you’ll have a personal tour guide, bf, along with amazing sex with a deep connection and chemistry. I’m here to please you. What do you want out of this?

Me: So you get money, travel, and regular sex. And I get yet another person to support, someone to drag along on my adventures, as well as being forced into monogamy with a guy using me for cash and sex? Sounds amazing.

Him: I’m open to whatever you are. If you want me to be your SoCal boy toy, I can do that. What would make this work for you? Once I start becoming a profitable trader, I do plan on teaching the woman who invests in me as well. I want to share my love and appreciation.

Me: I could really use a live-in nanny, housekeeper, and sex slave.

Him: I can’t move... I can be your housekeeper when we travel or when you are in SoCal. And I’ll always be your sex slave.

Me: Looks like your budding biz is going to need to hire me a local manny. Preferably one that can cook.

Him: I can cook when we’re together. I am open to visiting you up north for short periods of time. I also plan on using some of my allowance to join CrossFit so that I get bigger, stronger, and sexier for you. The last mutually beneficial relationship I was in, the woman loved having me as her eye candy and sex toy. It was great.

Me: I feel like maybe you’ve watched Deuce Bigelow one too many times. Also, how much of an allowance are you thinking?

Him: I’ve been in these types of relationships before and I’m drawn to them. What amount works for you?

Me: Let me see what’s in the kids’ piggy banks.

Him: Well, let me know what you think. If it’s not for you, I understand.

Me: I’m going to need references.



One night in my mid 20s, I met up with a woman from the internet at my favorite local bar. We partied long into the night and, of course, didn’t want to stop, so we got a ride back to her place and headed straight for the bedroom. So there I am, sitting in my underwear with her on my lap, when the door slams open and in storms some guy with a dog on a leash barking its head off and lunging at us. It’s soon revealed this is her ex; the breakup was NOT mutual. Her roommate storms into the room amid the yelling and pulls me to the living room so the two can “talk it out.”

I remember sitting on the couch thinking about my situation, when I noticed I’m in my underwear at 4 am on a stranger’s couch. To top it off, there are two women on the other side of the room making out, MDMA all over the table. Finally, the bedroom door opens and they go outside to talk. I look for my clothes so I can leave, but they’re gone! The ex threw them out the window!

I find my pants, one shoe, and my keys in a nearby alley, but my wallet and phone are gone. At this point, I snap. I put on my pants and one shoe, then I run inside to grab a baseball bat I saw earlier. I’m charging through the streets with this miniature “Hot Wheels” bat, probably scaring the shit out of anyone who happens to be out. An elderly man walks up to a bus stop near me, we lock eyes for second, he shakes his head and walks away.

I find the lovers fighting in a nearby park. She runs home, in tears, the second she gets a chance, and he tries to follow her but I quickly step in his way. At this point I think I just keep screaming, “Give me my wallet and phone or I’ll cave your skull in!” He threatens me with his dog again, but this time the dog is happily rubbing itself against my leg.

The ex eventually breaks down and tells me all about how “he isn’t over her.” I gently inform him that kicking doors down is no way win a lady’s heart. He walks, at bat-point, to where he threw my wallet and phone. My phone is destroyed, and my wallet is empty. I’m so furious at this point I just want to go home. I tell him to empty his pockets, and I take all the cash, calling for a ride to my car from his phone.

Driving home, I flagged down a cop so I could report the incident. Before I could get out they had guns on me and ordered me to the ground because “There’s been a lot of hate against police lately.” —Anonymous


I should have known better. But I was new to Portland, single, and eager to meet new people. I would go on dating apps, meet guys, and if they seemed polite after a couple messages, I would meet them in person. I don’t like small talk and going on dates was a great way to try new bars and restaurants while weeding out guys quickly if we didn’t click. The problem was I was too nice and stayed in uncomfortable situations way longer than I should have. The worst example was my date with Joe.

We had only exchanged a few sentences when he suggested we meet at a dive bar. When I arrived, he was at a table with a half dozen of his friends. I was expecting him to be alone, but he motioned for me to sit next to him. He put his arm around me and introduced me to all his friends: “Everyone, this is Beth.” THIS WAS MY FIRST TIME MEETING THIS GUY.

He was acting like we’d been dating for a long time, though I knew nothing about him. I felt I had to pretend to know him in order to make him look good in front of his friends. I should have run—but no, I went with him and his friends to the next bar for karaoke. AND (stupid me), I let him drive me to the bar, so I wouldn’t have to find parking.

When we arrived, he said his passenger door handle was broken on the outside, and he instructed me to close the door with the handle lifted so it would lock. If you can imagine pushing something that suddenly comes to a complete stop, you might be able to imagine how doing this caused my thumb to jerk back and sprain my wrist. I yelped in pain, and Joe ran from the other side of the car, embraced, and then kissed me. (AHHHH!!)

I told him I was fine as my wrist throbbed. I was livid during karaoke, and despite his urging I did not sing. I finally got a ride back to my car where he asked me what I was doing the next night. I told him I was going to a concert with friends, and immediately blocked his number. I don’t remember mentioning the venue or the band, but as I was leaving the concert, I was so creeped out by him I swear someone was standing across the street, watching me.

I partly blame myself for what happened... but screw him for taking advantage of my kindness. Years later, and I still have to go to physical therapy for my wrist, and I hate him for using that painful situation as an excuse to touch me.

I know now to leave a date if I’m having a bad time, and that I don’t owe kindness to anyone. But c’mon guys: Please don’t ever make a stranger pretend to be your girlfriend! —Anonymous


He’s Jewish, likes to bike, and has herpes: a trifecta of common ground! Plus he’s okay with going to an Indigo Girls concert for our first date and sweetly buys both tickets.

While walking past a cluster of protesters upset at Amy Ray and Emily Saliers for performing at the Oregon Zoo, he said he was recently punched in the face on an airplane. As he was sleeping with the shade down, a hand magically appeared to put the shade up. “The guy says, ‘My daughter would like to see outside,’ and I asked, ‘Well, does your daughter have the window seat?!’” He guffawed, pleased at his punchline... but not the actual punch he received from the father of the three-year-old.

While settling into a patch of blanket on the lawn, he told me about his bike ride earlier that day, when he chased an Asian man into the parking lot of an Amazon warehouse after the man had cut him off. He pounded on the car window. He screamed, “You could have killed me!” and then, as the man didn’t seem to comprehend, said “Don’t you speak English?’’

Some of the Asian man’s coworkers witnessing the spectacle ganged up on my date and accused him of being a racist bully. He took a gulp of his beer and said that as the Amazon security guard escorted him out, the guard confided that this was not the first time someone has complained about the way the warehouse employees drive recklessly into the lot. I doubted that last part, that the guard would tell him that, and I think he said it because he wanted to justify his behavior.

And yet? The voices in my head convince me he’s still a good match!

He marvels at “all the straight couples like us” and during a break between songs, he asked two black children with white adults nearby, “Are you brother and sister?” Then, as the kids watched, he asked their parents, “You adopted them? That’s so great!” and lifts his beer up in a toast. I try to express as much apology as I can in a silent expression.

Afterward I go to his place and we have sex in his bed, which needs to be unzipped to get into, because the bed is inside a plastic tent that simulates high altitude and is good for training.

In the bathroom, while trying to pee to avoid getting a UTI, I unmatch him on Tinder. —Anonymous


Brian asked me to meet him at Holman’s Bar and Grill on a Tuesday night because he “hates Portland hipsters and doesn’t want to be anywhere near them.” He arrived 30 minutes late, and instead of apologizing, he was flustered because happy hour was almost over. He flagged the waitress in a panic and ordered two plates of mini-tachos (tater tots smothered in nacho cheese), two plates of Saucey Strips, and two whiskeys on the rocks. He told me that he needed to get his full order in “under the happy hour wire.” Brian only goes on dates on Tuesdays and always to Holman’s because of their “Tightwad Tuesdays” specials of $2.50 drinks and $3.95 tachos.

He asked if we could switch seats in the booth because he wanted to “keep his eye on the Blazers game.” Brian ate the tachos and Saucy Strips in under 15 minutes without offering to share. The white sauce from the Saucy Strips dribbled down his chin as he told me that he “hates people who move to Portland from the Bay Area.” (I moved here from San Francisco.)

With a mouth full of tachos dipped in Frank’s hot sauce, he schooled me about timeshares. He owns one in Lincoln City and apparently, “timeshares are the way to go if you want an investment property that pays for itself tenfold.” He started in on his second whiskey before finally asking me a question. I was relieved that he noticed I was there at the table with him along with his tachos and Saucy Strips.

He asked, “So, do you think a woman your age is really going to find someone?” (I’m 44, he’s 47.) He continued, “I read a study that said it’s statistically more likely for a woman over 40 to be struck by lightning than to meet someone to marry.” He took a whiskey sip and added, “Actually, I think the statistics also show that there’s a greater chance of being a victim of terrorism than a woman finding love after 40.” He tipped his glass in my direction and winked, saying, “But it’s good that you’re still putting yourself out there. I guess you never know if you’ll be a statistical anomaly.”

He told me that he didn’t notice my age in my Bumble profile and that he usually only dates women under 37. I asked, “Why?” and he said, “I mean, you have to make a cut off somewhere, right?”

I’d nursed sparkling water and lime throughout the date because it was clear that this date was going to be a bust. I knew I’d want to take myself out for a beer when the date was over.

The waitress brought the check, and Brian asked, “Are you okay splitting it?” —Anonymous


Have you ever awakened to find that some stranger has gone through your entire social media account and liked every photo? In this story, it’s a he. I’m a lonely person, and it gets me in trouble. So I was intrigued.

Pretty soon after, he (we’ll call him Behringer) showed up at the center where I worked. He said he came there all the time, which was an obvious lie!

I suggested we go to a movie. We settled on

Her (sci-fi for me, emotions for him), and he stood me up. When I called to see why he was late, he said he was in class. “But if your class is the same time every week, why did you say this time would work?” I asked. He promised to pay when we tried again to make up for it, but he forgot about that too, so we went dutch.

Her is a hilarious farce of a film where Joaquin Phoenix falls in love with his computer, Scarlett Johansson. It’s like a sexism nosegay: a wide assortment of sexisms held together with attractive color schemes. I laughed many times and delighted in a pair of friends who were sitting behind us, loudly slurping their sodas during all the emotionally intense scenes. They were like The Shining twins, but with sad slide whistles.

“Those girls!” I laughed on our way back to the bus. Out of nowhere, he shouted, “You’re so sarcastic! You look down on anything with real emotion in it because you’re so removed and above it all, but really you’re just pretentious!” He began to weep. I felt horrible, but also like a person standing at a bus stop with someone who is weeping—so you know, uncomfortable.

The bus came, we sat together, and he cried on my shoulder. After taking a moment to consider things, I was fairly sure I was being mischaracterized, but it seemed rude to fight on a bus. “There, there,” I said, patting him. Abruptly, several people I knew got on the bus, looking at me like “Oh, hi. See you have a crying guy there.” I tried to shrug with the part of my body he wasn’t crying into.

The bus passed his stop and I realized he was going to try to come home with me. “We passed your stop,” I said. “Can I stay over?” he asked. “I don’t think I should be alone right now.”

Like I said, I’m a lonely person. It gets me in trouble. But he slept on the couch, and I stopped seeing him after that. —Anonymous

And Now, the Winner of the Mercury’s “Online Dating War Story Contest”....


In college, I wrote an anonymous dating blog. Think millennial

Sex in the City, except I’d never seen the show. I’d seen this guy around campus and when we matched on OkCupid, I was thrilled. He was perfect to write about, and could finally be the date that called me back. Let’s just say I thought of dating like it was my job... and I was really bad at it.

Night of our date: He was a total no show. No text, no call... which in his defense, who calls nowadays? No apology flowers outside my dorm, nor a note saying something tragic had happened and he was sorry... just silence. I tried to shrug it off, because at least I had something to write about. “The love that never was...” or whatever lame, vodka-soaked title I could think of.

The next morning, I woke up and followed my daily tradition of checking PDXMugshots.com. I studied criminal justice and religiously listened to the police scanner. This was before the mainstream acceptance of true crime, so it wasn’t exactly normal. (I’m not sure it still is?)

Anyway, there he was—right on the first page. A far less flattering photo than on his dating profile. He had been arrested on a first-time low-level assault charge. In all honesty, I appreciate he didn’t use his one phone call on me—that would’ve been a commitment I wasn’t ready for.

A few days passed and then… a text! My heart sped up; it was surely a misunderstanding? Mistakes happen, right? Maybe he was defending some innocent person being mugged? Or maybe he was a drunk asshole... I had to know! He asked if I’d go out with him, and I told him that I knew why he stood me up. He was quiet... give him another chance, he pleaded.

His idea of a romantic first date? Asking me to accompany him to court, because I was the most responsible looking person he knew. This relationship had “be my partner in crime” written all over it, and I fell hard.

I wish this story ended differently, that I didn’t say “Yes” to going to court with him, that I didn’t waste five years of my life taking him to DUI diversion classes and defending his poor treatment of others. But sometimes, you just pick the wrong guy.

So I genuinely hope if you can take anything from my story, it’s this: If you won’t listen to your intuition, at least listen to criminal records.—Anonymous

Congrats to “Anonymous” for winning the Mercury’s “Online Dating War Story” contest!