Being single comes with its own set of adventures—some hilarious, some downright baffling, and others that might just keep you up at night. Ever tried engaging someone on a dating app exclusively through food puns for a month? Or had a romantic moment at a bar ruined by a cockroach making an unexpected guest appearance? Yup, dating can be a real rollercoaster! And just when you think you’re getting the hang of it, you might discover that the charming guy you’ve been swooning over has a questionable past… like, a mug shot-worthy past! But fear not, as each dating blunder is just a step toward learning and growing—ideally paired with a healthy dose of laughter. This year, I’ve stumbled my way through the dating scene and collected my top mistakes from those awkward initial dates. So, grab some popcorn, settle in, and let’s dive into the “oops” moments that are all too relatable. Who knows, maybe you’ll get a kick out of my catastrophe stories and learn a thing or two for your own escapades – because we’re all trying to figure this out together. Ready to cringe and chuckle? Here’s the rundown! LEARN MORE
One of the greatest things about being single? The stories. Some are funny, like when you meet someone on a dating app and talk to them for a month only in food puns.
Some are bizarre, like that time you were hitting it off with a guy at the bar and a cockroach landed on your arm. (NYC, am I right?) And others are pretty horrifying, like that time you realized the guy you were swooning over was, at one point, a suspect in a major disappearance case. Mug shots don’t lie.
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With each mistake, we reflect, learn, and (eventually) laugh. But that doesn’t mean women don’t make mistakes. Because, trust me, I made plenty of big mistakes when I was dating this year — and some of them may some incredibly familiar.
It would’ve saved everyone time.
Yuri A / Shutterstock
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I know plenty of experts recommend it — and I’ll even tell my friends to do it! But it gets stressful. I wasn’t even really getting to know any of them because I was just trying to keep up and get all the facts straight.
And, when two guys you’ve gone on a couple of dates with, along with that guy you actually like, all text you at the same time and ask you what you’re doing that night there’s only one feeling: panic attack.
I made a conscious effort not to write people off so easily this year. But there’s a fine line between giving someone a chance, getting to know them, and recognizing they’re just not a good match for you. But come on, life, where is that line?!
Womp.
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But WHOOPS! I SENT THAT TEXT TO THE DATE. Who — guess what? — wasn’t even late. He was just in another part of the bar. My favorite shoe broke right after that, and I deserved it.
I wish I had appreciated the honesty and maturity — and not been scared by it.
Way too much time wasted on being upset over something I can’t control.
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On the bright side, it was a good exercise in persistence and patience for him. A+!
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Just kidding! That was not a mistake, but my overspending alerts disagreed.
Knowing what you want is a good thing — and you shouldn’t be afraid of it.
I imagine I’ll struggle with this one my whole life, but I’ll try my best to remember this: my feelings matter, too.
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Michelle Toglia is the Executive Editor at Elite Daily, overseeing the site’s entertainment, news, style, dating, and experiences coverage.