He Paid Someone to Mug Me and Other First Date Horror Stories

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The saving grace of bad first dates is that the really terrible ones are a little like childbirth—our brains experience a casual amnesia, forgetting most of the gory details so that we’ll keep dating until we meet the one really good date, the one that lasts forever.

But some first dates are so bad they slip through this self-imposed amnesia and become a permanent part of our dating narrative, the tale we retell over and over to other single friends to assure them we have it worse than them and to married friends to remind them why being single ain’t so great.

During my twenty years of dating I endured my fair share of great first dates and one that led to an engagement, marriage and a baby. But I also had plenty of disasters. There was the guy who smelled me and asked why I was still single. There was the guy who lived in his parents’ basement because he lost all his money playing online poker and there was the guy who took me to his cousin’s wedding on a first date without informing me we were going to a wedding. I caught the bouquet and got really drunk.

We’ve all been there! Bad dates are universal. They’re something everyone can relate to and bond over. That’s why we collected some of our favorites:

He Paid Someone to Mug Me
Jessica, 37, Fort Lauderdale, FL

When I was living in NYC I went out on a first date with a guy in his early 40s. He was attractive and we had a nice enough time. Things were getting late and I was ready to go home, so he offered to take me down to the subway station and wait with me until the train arrived. It was pretty desolate down there so I appreciated the gesture. We were on the platform for a while since the trains on the weekends run notoriously slow. All of a sudden a man came up from behind me and put his hands around my neck, pulling me into him very aggressively. Before I knew it my date pulled him off of me, sucker punched him in the face, beat him up, and left him bleeding and on the floor. We left the station right away and I was visibly shaken. My date put his hands around me, kissed me and insisted on taking me home. He was my hero…or so I thought.

About three days later I get a Facebook message from a stranger with an apology. It read something to the effect of, “Jessica, I am sorry about the incident on the subway the other night. Just thought you should know that the guy you were on the date with paid me to do that. Guess he thought he would score some action with you by being your knight in shining armor. I messed up shouldn’t have done it and I’m sorry.”

I never heard from or saw this person again.

He Was an Actual Sex Offender
Karly, 35, Denver, CO

I was on a date with a guy around Christmas time. We were driving around the suburbs looking at Christmas lights when he got pulled over. The officer approached the vehicle and asked for his ID and registration then informed him that he was pulled over for an illegal light on his vehicle. The officer went back to his squad car and then shortly another squad car approached. The officer returned to the vehicle and asked him to get out of the car and said, “Sir you have a warrant out for your arrest.” The officer then came to my side of the car and said, “Ma’am do you know why we are arresting him?” I said, “No.” He said, “We are arresting him for failing to register as a sex offender.” I found a friend who was able to drive me home.

He Was Proud of Not Paying His Taxes
Sara, 37, Berlin, Germany

It started out good. The guy was tall, handsome, very personable, and charming. But the date took a strange turn when he confessed that he doesn’t pay his taxes and that his identical twin brother is a meth addict living in Harlem, who occasionally breaks into his apartment and steals things for drug money. He asked me if I wanted to come over and see his place. I told him I didn’t think so.

He Still Got an Allowance
Megan, 41, Los Angeles, CA

This guy was older, about 60 years old. He started bragging about how wealthy he was and I took the bait. “What do you do for a living?” I asked with the right amount of skepticism. He proceeded to tell me his parents are very wealthy and that HE GETS AN ALLOWANCE. I don’t know about you, but I stopped getting an allowance at age 10. But then it got even better. He then told me he played baseball for the Phillies. He proceeded to take a baseball card out of his wallet and hand it to me.

I looked at the card and in the upper right hand corner it said, “Fantasy Camp.” “You don’t really play for the Phillies. You paid to go to camp and play with them,” I said to him. This just made him mad. I explained that it was like how going to space camp doesn’t make you a real astronaut. He then asked for the check.

He Let Me Get Soaked in the Rain (And Stole My Umbrella)
Laura, 33, Lafayette, CA

This terrible date was with a successful, young finance type. We went to a fancy restaurant in New York City and had good chemistry. The night was going well and he suggested we go to a wine bar after dinner. It was raining outside so he said we should hail a cab even though the bar was two blocks away. “Real men walk in the rain, right?” I teased. This shamed him into agreeing to walk. But then he grabbed my umbrella from me and proceeded to walk, alone, shielding himself from the rain and allowing me to be drenched. Half a block away I heard him wail like a little girl when he stepped in a puddle and screamed, “Ahhhh, my Tod’s!” Yes, he was crying over his fancy loafers. I hailed myself a cab and went home.

She Talked About Herself All Night
Jenny, 47, Houston, TX

We met on Tinder and got along really well via text. We laughed and talked about travel, love and life. I was super excited to go out with her because I thought we would really click. She was a nice Jewish girl from New York. How could I go wrong? She said we would have dinner, so I came to the restaurant hungry. When I arrived she told me she had already eaten. “Let me order for you,” she said. She ordered charcuterie. I like charcuterie. I love it, actually. Except I don’t eat cheese. The plate came and I tried to act normal while I ate every scrap of meat and scooted the cheese around the edges of the platter. She talked non-stop for four hours. Four. I don’t think I said more than ten words. Finally, she noticed my millionth yawn and said, “I guess we should call it a night.” I jumped up, flagged down the waitress and paid the bill. Then she said, “So I’d love to see you again.” I had the wherewithal to say, “I don’t think that would be the best idea.” “Why?” she asked. “I thought we really clicked.” She was clearly on a different date than me.

He Was Still Married
Micaela, 32, New York, NY

When I lived in Philadelphia I matched on Bumble with this super handsome doctor. He was from Mexico. Smart and sexy. His profile said he went to MIT, Harvard Medical School and was an orthopedic surgeon. I have a rule that I need to speak to someone on the phone before we go out. We talked on the phone and had this amazing and overly flirty (in a good way) conversation. He texted me a bunch of times each day leading up to the date. He would say things like, “Two nights left until I meet you,” and, “Good morning stunning girl.” I was pumped!

Over the course of the next few days our texts got deep in terms of where we both were in life. I told him that I was on Bumble to meet a great life partner and that I wasn’t looking for a hook up. He told me he was looking for the same.

He picked an adorable little restaurant in Philly. He gave me the double cheek kiss and a long hug when we first saw one another. Then he casually told me that he was planning on going to Texas with his wife and kids. “You have kids?” I said. He said he had two sons. He told me he was still legally married and that they were considering separation because he thinks she has a drinking problem. I asked why he had told me he was looking for the same thing as me and he told me that he wanted to meet me because I had soulful eyes. I then rolled said soulful eyes at him.

He Groped Me in Public
Ashley, 34, San Francisco, CA

I was on a first date at Golden Gate Park and all of a sudden, he asked what size bra I wore and reached over and grabbed my chest. It was a boob grab in broad daylight.

He Told Me He Preferred Dating Models
Amy, 32, Oakland, CA

I was set up by friends with a guy they told me was a better looking George Clooney. To his credit, he was incredibly handsome and smart. He was a college professor with a great job. We were having a good time and hitting it off. Then he asked me to come back to his apartment so he could order drugs. Yes, he wanted to sit in his apartment and do drugs the rest of the night. He proceeded to tell me that he liked talking to me because I was so real and smart, unlike his girlfriend (YES, his girlfriend), who was a young, hot “supermodel” type. “I only date models,” he insisted. “But hanging out with you is cool.”

He Wouldn’t Leave
Suzanne, 46, Lexington, KY

When we got to the restaurant he refused to order food and just got a beer. He just watched me while I ate. I tried to make small talk but it wasn’t easy. After dinner we went to dance club where he met up with his friends. Now, I am only 5’1″ and these guys were over six feet tall. He talked to them over my head and didn’t introduce me to a single one or try to include me in their conversations. It was awful! I was totally ignored and forced to stare at their arm pits! By 11 pm I had enough and was ready to go home. He drove me home and walked me to my apartment door. I unlocked the door and as I turned around to say thanks, he walked in. He proceeded to go into the living room, turn on the TV and ask if I had any beer. I just stood there and looked at him. I hadn’t invited him in. I didn’t even want him to come in! I gave him a beer and just sat there in the other chair across the room while he drank and channel surfed. Finally, I told him I was tired and ready to call it a night. He got up and asked which room was mine that he was ready for bed too! I looked at him and said, “I’m going to bed. YOU are leaving!”

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