Cringe-Worthy Philly Dating Stories to Get You Through This Valentine's Day


Philly is not an easy city to date in. It quickly starts to feel very small, and once you’ve spent about a week on any dating app, you’ll start to see familiar faces everywhere you go. You’re likely to run into paramours past at any given social event. But all of the bad aspects of this city's dating pool are made up through good-ass stories. Whether you want to feel better about your own dating life or crawl into a ball of despair, we had some of Philly's boys and girls share their worst anecdotes about dating in Philly to help you out during Valentine's Day this year.

"Next thing you know, the squirrel gets tangled in her hair."

“We met up at Cake & the Beanstalk -- I think it’s a hummus shop now -- and things are going good, we’re having a good conversation. We were sitting outside by a wall, a brick wall, and suddenly we see this squirrel running Matrix-style along the wall, headed for her. She starts freaking out and she’s like, ‘I don’t like this, I don’t like this... ’ but I keep laughing it off. Next thing you know, the squirrel jumps on her and gets tangled in her hair. It actually worked out though because I ‘rescued’ her from it and got to look like a knight in shining armor.”
-- Karthick, 24

"Man, this sauce is really good."

“We met on a dating site. We went to Pod and when we walked in, he informed me that he was losing his night vision and needed me to help walk him to our table, arm in arm (which was also awkward because he was six inches shorter than me). Eventually we got our sushi, and when he went for the dipping sauce, I had to save him from eating a chunk of wasabi. He tried to play it off and was like, ‘Man, this sauce is really good,’ even though he had completely missed the sauce bowl. I told him I was thinking of enrolling in an online graduate program at Quinnipiac and he basically compared it to the University of Phoenix and talked down to me about it. Later, in a text, I told him we should just be friends and he called me a bitch.”
-- Meg, 28

"Cow milk is for cow babies."

“I went on a blind date once with a movie executive. I was vegan at the time and put soy milk in my coffee. His response was something like, ‘Oh, you don’t drink milk? That makes sense actually. I mean, cow milk is for cow babies. And I’ve had this idea for a while. People should be drinking people milk. It makes more sense. We could pay women in third world countries a dollar a day to produce it.’ I excused myself, forever.”
-- Violet, 41

"Your name is Alex, right?"

“It was a lackluster OkCupid date. At the end when we were leaving the bar, she turns to me and says, ‘Your name is Alex, right?’”
-- Kyle, 29

"Apparently my grip is stronger than I thought."

“A friend of mine texted me from the hospital late at night. Message loosely read, ‘at hospital with my date.’ I asked for more details and got back, ‘Well, he’s getting stitches on his dick. Apparently my grip is stronger than I thought.’ I went back to bed.”
-- Amir, 31

"He tried to tell me how he’s 'racially colorblind'”

“I had just started using Bumble and was trying to be more flexible about my superficial dating preferences (distance, age, height, etc.). I’m in the city and he lived in West Chester, so we decided to meet in Media (a 45-minute drive for each of us). He seemed nice and functional, but within 15 minutes things got weird. He tried to tell me how he’s 'racially colorblind' (for context, this is a cisgender white guy who works for a wealth management firm). He then proceeded to show me photos of himself with 'some brown friends' he had recently made on a trip to Ireland to somehow prove his colorblindness. At that point, I knew I needed to tap out and stop trying to educate this guy. It was a long drive home, during which time he texted to say how amazing he thought the date went.”
-- Rachel, 28

"His nose suddenly started gushing blood."

“I was out on a second or third date with a guy I had met at a bar. We were driving to a party and his nose suddenly started gushing blood. He had to pull over so I could run into the Domino’s by Fairmount and grab him a stack of napkins. Then, when we got to the party, he started hitting on my roommate. Sigh.”
-- Monica, 22

"I had to stand there in my dress and heels and wait for him to finish swimming."

“I was supposed to go out with a guy who had asked for my number at The Cambridge. The plan was to meet outside his place first, so when I got there I texted to let him know I was outside. I thought he was meeting me out there, but instead he told me to come inside... to the indoor pool in his building. He was finishing his laps. I had to stand there in my dress and heels and wait for him to finish swimming and get dressed.”
-- Kit, 27

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Marielle Mondon is a writer from Philadelphia whose ideal date is one of those trampoline parks. Follow her on Twitter and Instagram @MarielleMondon.