5 Hilarious First Date Stories That Will Make You Cringe

First dates are always a bit awkward, but sometimes they can be downright cringe-worthy. From saying the wrong thing to wearing the wrong outfit, first dates often don’t go as planned. But that doesn’t mean they can’t be funny—in retrospect, of course.

Here are five first-date stories that will make you laugh, cringe, and maybe even feel better about your dating disasters.

  1. The “Ex” Factor

I once went on a first date with a guy who spent the entire time talking about his ex-girlfriend. He compared me to her, told me how she was a better kisser, and even showed me pictures of them together. I never saw him again.

  1. The Awkward Pause

I once went on a first date with a guy who didn’t say a word the entire time. It was so awkward that I ended up doing all the talking. I talked about my family, job, and hobbies—anything to fill the deafening silence between us. There was no second date.

  1. The Walk of Shame

I once went on a first date with a guy who lived in the same neighbourhood. We had drinks at a local bar and then walked home together. When we got to my street, he tried to kiss me goodnight—but I wasn’t interested. I politely declined and then watched as he walked away, looking dejected. The following day, I saw him walking down the street—wearing the same clothes from the night before. We made eye contact and then quickly looked away, pretending we didn’t see each other. It was so awkward!

  1. The Bill Blunder

I once went on a first date with a guy who insisted on paying for dinner—which I thought was polite of him. But when the bill came, he grabbed it before I could even reach for my wallet and then proceeded to leave without waiting for me to pay my half. I had to run after him and insist on splitting the bill—talk about embarrassing!

  1. The One That Got Away

I once went on a first date with a perfect guy—he was handsome, charming, funny, and intelligent. We hit it off immediately, and I thought he would be my boyfriend one day. But then he ghosted me—I never heard from him again after that first date! It was so frustrating because I thought we had something special.

First dates can be awkward, cringeworthy, and even frustrating—but they can also be funny (in retrospect). If you’ve ever had a dating disaster, rest assured that you’re not alone! These five stories are proof of that.

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