First Date Disasters That’ll Make You Grateful to Be Single

1. “The Double Date… With His Mom”

We matched on an app, and our conversations were actually pretty great-funny, flirty, and just the right amount of teasing. He suggested a nice Italian place downtown, which I thought was a good sign he was making an effort. I walk in, spot him right away… and notice there’s an older woman sitting next to him. He waves me over and says, “Hey! This is my mom, she wanted to join us so she could get to know you.” I laughed, assuming he was joking. Nope. She ordered for both of them, critiqued my choice of wine, and then launched into a very casual interrogation: “Do you want kids? How soon? Do you cook? What’s your stance on staying home with them?” He just sat there smiling like this was totally normal. By the end of the meal, she was telling me how she’d be “so happy” to help plan the wedding. I never texted him back.

2. “The Allergic Reaction”

We’d gone for a walk in the park, and when he suggested grabbing ice cream, I thought, “Sure, that’s cute.” I got pistachio, he got strawberry. We sat on a bench, chatting, when he suddenly stopped mid-sentence, staring into space. His face started swelling, like visibly in seconds. Turns out, even though he knew he had a severe nut allergy, he didn’t think to check if my ice cream might have touched anything. He didn’t have his EpiPen on him, so I had to half-carry, half-drag him to my car and drive to the ER. On the way, he kept mumbling apologies between gasps and saying, “You’re so sweet, this is just bad luck.” Sweet? Sure. Romantic? Not exactly. After four hours in the waiting room, I drove him home and we never spoke again.

3. “The Business Pitch”

We met at a coffee shop, and I thought we’d just… talk. You know, normal first-date stuff. He walks in with a leather messenger bag, sets it down, and says, “You’re going to love what I’m about to show you.” Out comes a laptop, and suddenly I’m in a full-on pitch meeting for his “revolutionary health supplement business.” He had slides, market projections, and something about “ground floor investment opportunities.” It slowly dawned on me that I wasn’t on a date-I was being recruited for a pyramid scheme. When I told him I wasn’t interested, he said, “Don’t worry, we can still build a life together without you being a business partner.” I finished my coffee, smiled politely, and left. He emailed me three times after with “investment updates.”

4. “The Silent Movie”

He picked an indie theater because “it has more personality.” I assumed we’d watch some quirky, artsy rom-com. Nope. It was a silent, black-and-white film from 1923, with French subtitles. Neither of us spoke French. The plot was incomprehensible, the music was weirdly intense, and the only other people in the theater were two elderly women knitting in the front row. About 20 minutes in, I whispered, “Do you have any idea what’s happening?” and he admitted he’d picked it because “it looked cultured.” We bailed halfway through and ended up eating hot dogs from a street cart in the rain, talking about our favorite trashy TV shows. Honestly, that part was great… but the date started like an awkward art school project gone wrong.

5. “The Escape Room Nightmare”

His idea was “something unique” for a first date, so we booked an escape room. In theory, fun. In reality? A disaster. We got paired with two random strangers who immediately started arguing about every clue. My date apparently saw himself as the “team leader” and started barking orders at everyone like it was a military drill. At one point, I was trying to solve a combination lock when he leaned over my shoulder and said, “You’re not even trying hard enough.” Sir, we’ve known each other for an hour. We escaped with five minutes to spare, but the second that door opened, I headed for my car without looking back.

6. “The Wrong Date”

I was sitting in a café, texting my date that I was “at the table by the window.” A guy walks in, looks right at me, smiles, and sits down. We start talking—about travel, pets, and food—for a solid 20 minutes. He was nice enough, but I kept thinking, “Wow, he looks different from his pictures.” Then my phone buzzes: Hey, stuck in traffic, be there in 10. My real date hadn’t even arrived. The guy across from me just smirked and said, “I figured you had the wrong person, but you seemed interesting, so I didn’t stop you.” I awkwardly excused myself and had to go through the whole “nice to meet you” process all over again—twice in one night.

7. “The Magician”

At first, he seemed normal—funny, nice smile, good conversation. Then the breadbasket arrived, and out came a deck of cards from his pocket. I laughed, thinking it was a quirky party trick. But no… every lull in conversation became another magic trick. Cards, coins, salt shakers—nothing on the table was safe. At one point, he asked the waiter to participate in a “grand finale.” When the bill came, he said, “Watch this,” and pretended to make it disappear. Spoiler: it didn’t. I paid for mine and left while he was still rifling through his wallet.

8. “The Crying Ex”

Everything was fine for the first half of dinner—good food, easy conversation. Then I asked why he seemed a little distracted. He took a deep breath and said, “My ex got engaged today.” I tried to offer a sympathetic “I’m sorry,” but he was already pulling out his phone to show me pictures. The rest of the night was a narrated slideshow of their relationship, from their first vacation to the day they broke up. He teared up several times, the waitress brought him tissues, and I honestly felt like a therapist on call. I left that date emotionally drained and with zero appetite for romance.

9. “The Cat Test”

He invited me to his place for a home-cooked dinner, which sounded sweet. I walked in and immediately saw… cats. So many cats. I counted at least six, roaming across the furniture and eyeing me like they knew I didn’t belong. I told him I was allergic, and he said, “Oh, they’re part of the package—you’ll get used to it.” I lasted maybe 15 minutes before my throat started closing and my eyes swelled shut. He suggested I just “take some allergy pills” and power through. I left wheezing and never went back.

10. “The Parking Lot Proposal”

We’d just had a perfectly fine diner date—nothing amazing, but pleasant. As we walked to my car, he suddenly dropped to one knee and pulled out a cheap plastic ring from a vending machine. “I don’t want to waste time,” he said. “I think you’re my soulmate.” I laughed nervously, assuming it was a joke, but he looked dead serious. When I said it was way too soon, he looked hurt and said, “I just know what I want.” I got in my car, mumbled something about needing to think, and drove away like I was escaping a heist scene.

11. “The Taxi Meter Guy”

He was charming over drinks—funny stories, nice laugh. But when the bill came, he suggested we split it “fairly,” which was fine… until he pulled out his phone, opened some taxi meter-style app, and started calculating the cost per sip based on what we’d ordered. He actually tried to charge me more because my cocktail had “fancier ingredients” than his beer. When I said I’d just pay my half and go, he looked offended and said, “I thought you were the kind of person who appreciated fairness.” I appreciated walking out more.