Worst First Dates in History (3-Hour Compilation)

Worst First Dates in History (3-Hour Compilation) 30 Of The Worst Dates Ever, As Per Servers Who Witnessed Them When you go on a date at a fancy restaurant, cozy cafe, or, heck, even your local fast food joint, you can easily forget that there’s always someone around in the background—your server. Now, odds are that most people working in the food service industry don’t eavesdrop on purpose. However, when a date goes frightfully wrong, they can’t help but notice what’s going on at one of their tables. We’re featuring some of the stories about the most awkward and weird date fails, as witnessed by servers and shared on these two r/AskReddit threads here and here. Scroll down for some of the most cringe, dramatic, and weird romantic encounters that waiters couldn’t look away from even if they wanted to. However, one note of friendly advice for you, Pandas: the stories here might give you some a case of some serious secondhand embarrassment. Bored Panda was interested to learn more about dating, whether restaurant dates are a good idea, and what to do if you see that you’re not clicking with someone, so we reached out to certified relationship and self-love coach Alex Scot. Scroll down for our full interview with her, Pandas. Relationship coach Alex opened up to Bored Panda that she personally isn’t a fan of “the stereotypical coffee or restaurant date” because many people feel a lot of pressure “to keep the conversation going with fewer things around to remark about.” In short, going to a cafe or restaurant might not be ideal for a first date. “If you’re the extroverted type, these kinds of dates are easier for you to show up and be you, but for introverts or anyone who has social anxiety, this can be a triggering environment. I personally feel it's a smarter move to go on some kind of activity date,” she said. Support this podcast at — https://redcircle.com/best-of-reddit-stories-2025/exclusive-content Advertising Inquiries: https://redcircle.com/brands Privacy & Opt-Out: https://redcircle.com/privacy