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Let’s face it—we’ve all had a shocker of a first date at some point. The kind that makes you question your taste in people, your life decisions, and sometimes even your sanity. As a dating coach, I’ve heard stories that range from mildly awkward to absolutely wild. So I figured it was time to share a few of my favourites—anonymously, of course—and offer a few friendly lessons along the way. If you’re reading this while prepping for a date, take notes. If you’re just here for the laughs, enjoy.

1. The “Surprise” Plus One
One woman showed up to her dinner date only to find the guy had brought his mum. Yep, his actual mother. “She likes to meet my dates early,” he said, proudly. Lesson: boundaries are attractive. If you need moral support for your date, bring your confidence—not your parent.

2. The Interview Panel
One poor bloke told me he went for drinks with a woman, only to be met by three of her friends sitting in the corner taking notes. She called it her “screening squad.” Lesson: dating’s not a job interview. Your friends can debrief after—not during.

3. The Food Shamer
A guy told me his date watched him eat his burger, looked disgusted, and said, “I only date vegans.” Then she stayed for dessert. Lesson: if you’ve got dealbreakers, be upfront before you judge someone’s cheeseburger. Kindness matters more than kale.

4. The Silent Treatment
One woman said she made it through an entire lunch date where the guy answered everything in one-word replies. Turns out he was nervous… or mute… or just not that into her. Lesson: silence may be golden, but not on a date. Make an effort, or politely pass.

5. The Crypto Proposal
A man shared that his date brought a laptop to the bar, opened a presentation on blockchain, and offered him the chance to “invest in their future together.” It was, quite literally, a pitch. Lesson: if your first date ends in a whiteboard presentation, you’re probably not vibing. Save the sales talk.

6. The Ex-Files
One woman was treated to a full play-by-play of her date’s previous relationship. “She was amazing,” he said. “I don’t know why she left.” She figured it out pretty quickly. Lesson: if you’re not over your ex, take the time to heal—don’t drag someone new into the heartache.

7. The Phone Addict
A guy said his date spent the entire evening scrolling, giggling at TikToks, and occasionally saying, “Sorry, what did you say again?” Lesson: dating is a two-person sport. Be present. The only thing worse than being ghosted is being ghosted in real time.

8. The Dog Date
One woman told me her date brought his dog. Not a small handbag dog—a 40kg slobbery beast who promptly ate her fries and peed on her handbag. “He’s just excited to meet you,” the guy said. Lesson: love your pets, but maybe introduce them later. Unless it’s a walk in the park, leave your furry mate at home.

9. The Escape Artist
A man recalled a woman who excused herself to go to the bathroom after the entrée… and never came back. The staff eventually confirmed she had slipped out the back door. Lesson: honesty is easier than hiding. If you’re not feeling it, say so. Ghosting in person is a low move.

10. The Marriage Talk
And finally, a woman confessed she brought a binder to her first date. It included life goals, baby names, and a proposed wedding timeline. “Efficiency is sexy,” she said. The poor guy barely made it through his coffee. Lesson: dreaming about the future is great. But maybe wait until date three before naming your imaginary children.

Now, before you judge these poor souls too harshly, remember—dating is weird. It’s vulnerable. People panic. People overthink. People try to impress and sometimes completely miss the mark. The point isn’t to laugh at them (okay, maybe a little)—it’s to learn from them.

Here’s what all these disasters have in common: they’re about people trying too hard, not being authentic, or completely forgetting that dating is supposed to be a conversation—not a performance. If you’re going on a first date soon, here’s the best advice I can give you: keep it simple. Be curious. Be yourself. And be kind.

Not every date will be “the one.” But every date should be respectful, honest, and grounded in reality. If you show up that way, you’re already ahead of the game.

So whether your last date was a dream, a dud, or somewhere in between—cheers to the stories we gather along the way. Because even the worst first dates make for the best tales later on.

– Dating Dave