Winner

It's 2009. Connect with a guy on Plenty of Fish. He picks me up at my house. We head to an ice cream shop. He has just come back from army basic training and the topic of conversation will only be about what physical stuff he has learned how to do there. I try to change the topic to literally anything other than how fast he can climb something and hand-to-hand fighting tactics, but to no avail. We exit the ice cream shop. He puts me in a headlock. The patrons inside silently watch me flail about, trying to escape. He releases me from the headlock, explains how I should have escaped his hold. We head to the movies. We sit down in an empty theater. He cranes his neck, thinks he hears something. Leaves to go check it out. Ten minutes go by. I hear something on the floor to my left. He's army crawling toward me on his stomach about to grab my ankles and scare me. We finish the movie and leave. Never to see each other again. —Jessi Miles

Runners Up

On a second meeting with a man, I invited him over to my place. We agreed he would leave when it got dark (I had to pack for vacation). As it got time to leave, he wouldn't move. I saw him take a swig from a fifth of something he stashed in his backpack. He began slurring his words and I had to holler to get him out. It took a few minutes of hollering. As we left the bedroom, I saw his boxers so I picked them up and handed them to him. He tossed them over his shoulder into my bedroom without looking back. Since he was too drunk to ride the bus, I drove him home, except I didn't know his address and he wouldn't tell me. On the way I demanded his wallet so I could look at his ID and get his address. Five minutes of fumbling in his pocket and he pulls out his wallet. Except this wallet was a tin of Altoids. He was incoherent at this point and I'm not sure how he got there so quickly. I thought he was pretending to be drunk until I dropped him off at the Dicks in his neighborhood, because I still didn't know where he lived and he was speaking gibberish at this point.

When he got out, he stumbled across the parking lot and into the street without looking. I waited until he was out of sight then went home. When I got there, I realized he had left his backpack. In it was his wallet and ID, the death certificate for his child (who died by suicide), and some key papers. I brought it to him the next day and gave him another chance. I still regret that. —Anonymous

I met a man on OkCupid. He was 36 years old, a 92 percent match, "ESTP," "drama-free," looking to "find someone intelligent, down to earth, and can keep up with [his] depraved sense of humor." He went on to say that he was at a tech startup and on the weekends he was "on a quest to find new and fun activities." He had a gorgeous dog and he didn't eat kale. Oh, and he was "really good at treating you like a princess."

We instantly connected, texted incessantly, and became Snapchat friends. We had plans for Monday and it couldn't come soon enough. But since I google my dates first, I did a quick search... and I found him:

"Wig-Wearing Bank Robber Finally Caught."

There he was in all his glory. This uber cute guy I had a date with IN TWO DAYS had allegedly robbed a bank less than a year ago.  

I then found his wedding website declaring he was supposed to be married in October 2015, but was arrested the day before. He went to jail until February of 2016 and his return to social media showed he was happy to be back with his dog. When I asked for more details, he admitted that his fiancée left him when he came clean about robbing a bank and he was just trying to live a normal life before HIS TRIAL. When I Snapchatted his own headline to him with "WTF" on it, his first question was, "How did you find my last name?" I told him he didn't need to worry about that. His second question was "So I guess our date it off?" Yep, genius, our date is off. —Julie Nashawaty

I usually make the guy come to me or meet me half way on the first date, but this guy suggested this really cool bar by him that I wanted to check out. I drove almost an hour to meet him. We had texted for a couple days prior to meeting and he seemed like a decent guy.

When I got to the bar, I saw him right away and approached him to introduce myself. Once I approached him, I was shocked by the first thing that he said to me. It wasn't "Hi I am so and so," or "Hi nice to meet you," or "Thanks for driving all the way here," it was "How's your asshole?" I didn't know what to say, so I just sat down to continue our date and hoped it would get better.

Immediately after sitting down to order food, he took his menu and hit me on the face with it, pushed my menu forward to hit my face, and kept grabbing me. I yelled at him to stop. He also did the 3 Stooges thing where he said I had something on my shirt, then when I looked down, he flicked my face. I knew there was no way I could get through the night with him. I looked at my phone and noticed my dad texted me. I lied to the guy and said that my dad needed me to call him real quick, so I needed to step outside and will be right back.

I walked outside, blocked the guy's number and dating profile, went to my car, and drove an hour back home. I was only with him for five minutes! I have had so many bad dates, but this was the worst! —Brea W.

He was cute and into films and comic books. I struck up a conversation online, where we chatted about our common interests and whatnot. He almost immediately started calling me "baby," which isn't my cup of tea but I figured it was whatever. After texting, we decided to meet up in Capitol Hill. 

I mentioned that we could grab a slice at Pagliacci's, which is my favorite pizza place. He started talking about how he knew this better pizza place, so amazing it would blow my mind. I said okay, cool, let's meet. 

The plan was to meet at Goodwill, since we both loved to thrift, then go eat and have drinks. 

Well, he was late... 30 MINUTES LATE. He just didn't leave his apartment until I was already at Goodwill. I wandered around, feeling like a fool. I stuck around though, and he finally showed up. The first thing I noticed was that he didn't really look anything like his photos. Yeah, the features were the same, but the overall look was way different.

Finally, we left to go get pizza at the amazing place, which was supposed to be right next door. Instead, we wandered around in the pouring rain while he smoked cigarettes. We came across a pizza place and each got a slice. When he asked me how it was, I said it was pretty good, and he said, "Yeah, I've never been here before."

After eating, I texted my sister to please come pick me the hell up. 

I told him goodbye. We hugged and he tried to kiss me, which I pretended not to notice. After I got home, he texted me that he had fun. He told me I didn't talk a lot, but he liked that. 

I promptly blocked him. –Sam M.

My line was recently hit up by a guy that I had first met online about four years prior. We agreed to meet for drinks at a local tequila bar. I didn't know what direction the night was going to go in, so I put on my best turtleneck in preparation.

I arrived at the bar a few minutes before nine when I received a text from him explaining that he would be late. I went ahead and ordered a cocktail without him. He arrived 45 minutes later and apologetically offered to buy me a drink. Everything went smoothly at first. As we finished our drinks, he said to me, "Let's do shots." I agreed.

He asked to see the bottle of their most expensive tequila. I found it hard to believe that top shelf liquor was in his budget. It was clear that he was just trying to show off. I rolled my eyes as he took a picture of the bottle. We took the shots and he quickly ordered margaritas for us both. I noticed that his speech had begun to slur. He went to take a sip of his drink. His depth perception must have been off because he smashed the glass on the table, dowsing everything in margarita. He demanded another drink on the house.

Overwhelmed, I reminded him that he broke the glass. I escaped to the bathroom for a moment only to return to a bill at my seat. The tequila shots were on my tab and he got that drink for free. He wasn't planning on tipping, so I made sure I left at least 30 percent. I have not been back to that bar since. Please make sure your date isn't on Xanax before going to a tequila bar. —Derek Groves

He arrived late. Instead of making eye contact and greeting me, he reached behind my back to poke me in the ribs. He immediately asked for a sip of my coffee and later asked again. Minutes in, he used what I thought was an inhaler but soon found out was a tobacco vape.

My coffee was weak and I didn't want it. He badgered me about ordering another drink, asking repeatedly whether I wanted another coffee. I said no thanks, repeatedly. He then shouted at the bartender to bring me another coffee: "One that isn't weak and horrible!" I turned to him, said firmly. "I don't want another coffee!" and apologized to the bartender. Unfortunately, snacks were already coming.

He's so awkward. Can't figure out if he's on something or just odd; weird eye contact. Brags about his wealthy family, boarding school in Dubai. Moved to the US for college and found all Americans "stupid." His example: a woman in his class who wanted to learn "about Egypt and Africa." Imagine her stupidity. Every story classist, sexist, entitled.

I plan to leave as soon as I can get the check.

I try to get the bartender's attention. Dude doesn't notice, texting, for about 30 seconds.

Him: "I'm racist but that's okay, I'm racist against everyone, including my own kind." I finally get the check and pay and stand. Him: "When's the last time you had sex?" Me: "That's incredibly inappropriate." He scoffs angrily. Me: "Why would you think it's okay to ask that?" Him: "I just figured we'd never see each other again." I put on my coat. Me: "Do you even understand why that's inappropriate?" Him: "No, but I'd like you to tell me." Me: "That's not my job." I walk out.

Him (yelling): "Guess it's been a while, then!" —Emily P.

I was swiping through Bumble and came across this hot guy. Let's call him "Ass Blower" for now. It'll make more sense as the story goes on.

Ass Blower asks me if I'm down for a casual hookup and of course I am, but since I don't want to end up disposed in a back alley, I ask him if we can meet up for a drink first. We met at Pine Box and Ass Blower looked damn fine. He checked all the "this dude doesn't look too crazy" boxes, so we headed back to his apartment to go to pound town.

We got to his apartment and he whipped out a bottle of wine and said, "We're gonna get drunk and do some kinky shit you've never done before." I'm secretly thinking, "Okay dude, just because you did anal once in college doesn't make you kinky." Little did I know I was in for some weird kinky shit that night.

First, Ass Blower whips out a plethora of toys including a double-sided dildo, vibrator, and air pump. Yes, a fucking AIR PUMP. Fast forward maybe an hour (who's really keeping track honestly?) after some anal prep and fucking on his porch (hello, exhibitionism), he whips out his handy dandy AIR PUMP. Turns out this dude's fetish is blowing air into asses and listening to it come out. He wanted to hear me blow a big JUICY fart. Anyways, Ass Blower proceeded to pump air into my ass and I legitimately thought I was going to blow away. There was so much air in me I was farting, queefing, and burping something fierce for what felt like days after. —Anonymous

In 2016, I ended a sexless six-year relationship. I was 26, just starting my career as a teacher, and on Tinder for the first time.

A year of swiping led to several unsuccessful dates—none as horrific as the one I had three days before the election.

He seemed all right at first. But things went south quickly. First, he demeaned my career choice; he mansplained that teaching is not actually a difficult profession, based on what he remembered from high school. As if babies can speak to the pain of childbirth…

Later, he snapped his fingers at the server to get her attention and asked about featured cocktails. While I sat cringing, he continued to disrespect her in front of me and when she walked away to get our drinks, he smiled smugly and WINKED at me (as if he thought I'd be impressed with his dominance). I tried to change the subject. The election was only a few days away, so we turned to politics. And that's when he dropped this bomb: "I haven't actually voted yet, but I think I would vote for Trump if I knew he would die and MIKE PENCE WOULD BECOME PRESIDENT."

I felt my stomach lurch and excused myself to go the bathroom. Instead I went to the bar and apologized to the server for his behavior. She understood and gave me another drink on his tab. I finished it quickly while calling a Lyft and left before he could start looking for me. I spent the next evening with a hot musician who loved eating pussy and who assured me he'd voted for Hillary Clinton.

Misogynists please, save us all some time and identify yourselves in your bio. Or better yet, jump off a cliff. —Anonymous

The summer I moved to Seattle, I spent a lot of time studying for a professional exam at a particular coffee shop. There was a cute guy I often saw there, making his art. One day we connected on Bumble (we all know no one talks to strangers IRL in Seattle) and he asked me out. He told me to meet him at a restaurant where he would be sitting outside at a table.

Well, he was there—with what I have to assume was black Sharpie all over his face. More specifically, at least 50 black circles gradually expanding and contracting in size along the contours of his face. Every inch of his face. If I had seen it on an episode of America's Next Top Model, I would have thought it was fierce. But this was not ANTM; this was Pike Street.

I asked him about it and he claimed to have done it himself; it's called "striping." (Is that a real thing? By the way, I feel like it might be appropriate at this point in the story to mention this was a skinny Scandinavian guy. Maybe not?) As if it wasn't bad enough to be new in town sitting across from this man in public on one of Seattle's popular thoroughfares, it was August, and as beads of sweat began accumulating on his forehead, cheeks, and nose, the ink-dots began to coalesce.

By the end of the date, it looked like he had on blackface. Need I say more? On a positive note, he was totally polite and even said some meaningful shit about my grandpa's passing (which came up on our first date...?). Unfortunately, we still see each other at the coffee shop. We just act like we don't know each other. —Anonymous