The Exact Moment The Date Was Ruined – As Recalled By PlentyOfFish Users

Ever been on a date and thought it was going well, only to have it go completely off the rails in the blink of an eye? Be it something you said, something you did, something someone else did, or something completely out of your control? We know your pain.

We had PlentyOfFish users weigh in on the exact moment they knew their date was ruined:

“Right after dinner a condom flew out of my pocket while retrieving my wallet.”









“The hostess greeted me and my date: ‘Welcome back Steve. Would you like the usual?'”












“I picked up my date and had forgotten I had put a pair of handcuffs over the passenger sun visor (I was a part time security guard), so when she went to use the vanity mirror and they fell off into her lap…….she screamed and ran back into her house.”









“I was holding hands with a date while walking through a downtown park. He asked me if I was going to an upcoming Nickelback concert. I told him no, and he asked why. I said… “because they suck”. Not much was said after that, and we never went out again.”










“I made the mistake of telling a woman friend a funny story about me masturbating. Within a week I was asked out by one of her customers, a local attorney. During lunch he told me that my friend had mentioned the story, and that he found it rather appealing.”









“We discovered we had opposing political viewpoints after just a few minutes of getting to know each other. This was a deal-breaker.”








“I used to keep toilet paper in my back seat to blow my nose. When I picked up my date for the first time she asked what it was for. I asked to her to guess. She said…well, pleasuring yourself? That was awkward.”









“I was just a wee pup of 19, and I went to go pick the girl up. I got there, and her family was gathered out back in their huge backyard taking turns riding a 3-wheeler.  I didn’t want to ride the thing, but her Mom and Dad insisted that I did. So, I got on it, and minutes later, ended up crashing through her Dad’s shed. The thing fell apart, and I ended up getting my face scratched up pretty bad. Needless to say, the date was cancelled, and another was never arranged.”







“One date, the night was wrapping up on my sofa. We were getting hot and heavy when she mentions she might be pregnant. It happened at a party a week ago with a guy I also knew. That was like a cold shower for me.”



Back in late 1972, I took a first date to a showing of what I thought was The Heartbreak Kid. Well, we somehow took a turn and ended up in the wrong theatre, and Deep Throat suddenly comes on the big screen. She was disgusted to say the least, and I was mortified. I think I blacked out the rest of the date from my memory.