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Unhinged, A Dating Series: The Cringiest Dating Stories in SD

We asked our Instagram followers to share their worst experiences while trying to find love in the city—their answers didn’t disappoint
Unhinged: A Dating Series, worst date stories

When he knocked on my door to pick me up for our date, I was already dressed and ready to go. At the time, I was living in Lake Merritt in Oakland, and Justin (not his real name) lived an hour away. My friend, his cousin, had set us up.

That was the only reason I had given him my address before meeting him. Opening the door, I saw him standing there dressed in sweaty workout clothes, gym bag in hand. “Can I use your shower?” he asked.

Since we had a mutual connection, I let it slide, hoping that maybe he had a good reason for not being ready for the date before arriving at my place. Once we finally made it to dinner, he continued to talk only about himself, rarely asking me questions

By the time we got back to my place, he was too drunk to drive home. I told him he could sleep on my couch, and I went to the bathroom to get ready for bed. But when I opened my bedroom door, I found him lying in my bed… naked. Nope. I moved him to the couch, where he stayed well into the next afternoon, not picking up on my hints that it was time for him to leave.

When he finally dipped, he kissed me and said he hoped we could do it again sometime. Sir, read the room, I thought. I never saw him again—but he’s married now, and I’m not. So, who really wins here? TBD.

We all have bad first date stories, cringe-worthy moments that make us wonder what’s really going on in someone’s head. So, for this week’s edition of Unhinged, we decided to ask our Instagram followers to share their worst dating experiences. Married and long-term-relationship folks, if you’re wondering what it’s like out there, have no fear—here’s your answer.

Stories have been lightly edited for clarity.

San Diego Dating Horror Stories

Dated for three months. Had our first disagreement and he cried, saying he just wanted to talk to his mom. This man was 38 years old. @dreamondreamr  

Homie gave me a ride home, leaned in, lifted my arms, and went to make out with my armpit. @vagrantcook

Me: Oh, you live by Mount Soledad! Cool, let’s go hiking tomorrow! Her: I need to wait until June 24th. Me: Why? She sends me a pic of her ankle monitor. @charlietiano 

The whole effing reason I got on dating apps was to meet and spend time with someone in real life. Met a dude for drinks. After exactly one drink, he says he needs to go home to “take care of something.” Turns out he had to run so he could play video games and would rather text me. WTF!! @chickenpsychedelic

I went on a date with someone who got up and left me sitting alone in a park because I said I didn’t agree that Lord of the Rings was the best book and movie series of all time. Didn’t even give me time to explain. Just asked if I was serious, and then left.@meghpie

Went to sushi on a set-up date. The guy was late, then went to the bathroom for 10 to 15 minutes while I was at the table. He came back and told me he died in the bathroom and had to hit himself in the chest to bring himself back to life. As a medical professional, I knew this wasn’t a thing. Asked him if he had anxiety or got panic attacks. He said no and said he had to go to the ER. I asked him if he had anyone to take him and he said no, so I ended up in the ER for three hours with him. He asked me out again after, and I said no thanks. Then he called me a c**t. @nicole_jonelle

On our one-year anniversary, my boyfriend at the time said he couldn’t do anything but brunch that day because he had to work on his nearly million-dollar condo that he’d just bought. No card or flowers in hand. The check came, and he asked to split it. Worst part? I stayed for another six months. @mckenna.bean

I went on a first date with a guy and we were discussing places to go to after dinner. The next place I suggested, he goes, “Oh, no, no. I’m banned from there ever since I beat that guy with a crowbar. I can’t go back.” I’m sorry, what? “Oh, he’s fine; no big deal. Let’s think where else could we go.” @candacelately

I took a date with me and some friends to Valle. In the line on the way back into the US, she had a meltdown. “If I would have known this line was going to be so long, I never would have come!” The line was an hour long. @bajasocietytours

Went on a few dates with somebody and he ended it after Mother’s Day because he told me I look too much like his mom. @kjohaaaay

Met him out at a bar and he offered me a leftover slice of his pizza. I ate it. He asked for my number and the next day asked me out on a date to a “really good Italian spot” by his apartment. When I got to his place, he gave me a “tour,” which included his bathroom that was completely wallpapered with Playboy magazine covers. I laughed. He looked at me and said, “I did it myself” (and was VERY proud). I ended the date right then and there (before it even started). @leahguirrelcsw

My husband and I are polyamorous, and I used to run a poly meetup group on FB. There was a girl who was always supportive but never would show up to anything and had excuses for everything. So, two years later, she wanted to go on a date with my husband and me. I should have known that it was going to be bad when she showed up wearing an outfit that looked like she got it out of the dumpster. If the outfit wasn’t the biggest red flag, my then-boyfriend invited her over to his place, and she would not leave and tried to squat at his apartment and tried to convince him to break up with me and be with her. I went downstairs to her car and it was literally trashed—filled to the brim with clothes and trash. Found out that this is called being a “hobosexual”… She still tries to hit up my husband.

I accidentally dated a homeless man who turned into a stalker. @bcmuu

Went out with a guy from Hinge who had been getting increasingly creepy as the date went on, so much so that the bartender had to keep an eye on us. Ultimately, he said that his therapist said he shows sociopathic tendencies, which he should’ve let me know before. @btchykryssy

Want to join the conversation? Add your worst San Diego date story in the comments or email us at [email protected].

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

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By Nicolle Monico

Nicolle Monico is an award-winning writer and the managing digital editor for San Diego Magazine with more than 15 years of experience in media including Outside Run, JustLuxe and The San Francisco Chronicle.

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