“Why did he kiss me like he was performing CPR?”

That’s the question I found myself asking my best friend one rainy afternoon in a Brooklyn café, somewhere between my third cappuccino and her gut-wrenching laugh that turned every eye in the room. I had just recounted the latest disaster in my dating saga: my weeklong fling with a man whose approach to intimacy could best be described as "enthusiastic lifeguard energy."

Here's the thing: dating is a theater in which all of us—regardless of rehearsal time—must ad-lib our way toward connection. Sure, you might have a stellar opening act, but sometimes things take a hard left at intermission. Missteps are unavoidable, misreads are frequent, and occasionally, you get metaphorically kissed like you're choking on a pretzel.

So, where does that leave us? Hopefully in a place of learning and, dare I say, a little humor. Mistakes in dating aren’t just inevitable—they’re essential. They serve as mirrors, reflecting back the things we didn’t see coming and leaving us with hard-earned clarity. Let’s take a look at a few dating stories gone awry and the wisdom they left behind, including a particularly memorable episode of my own.

The Over-Communicator: When Sharing Becomes Oversharing

Picture this: you’re hovering over yet another overpriced cocktail during a first date, and within 15 minutes, your dining partner has divulged their entire life story. Childhood traumas, last week’s therapy session, their detailed horoscope chart—complete with an explanation of Pluto’s retrograde. The specifics don’t matter except for one—this wasn’t a conversation. It was a monologue.

Years ago, I found myself on the receiving end of such an info-dump during a blind date (an experiment I’ll never repeat, thank you very much). By the time my date concluded Act Three—“Why My Parents' Divorce Still Hurts”—I was internally yelling “CUT!” Sure, I left the table feeling like her memoir's first draft, but also completely confused by who she actually was.

What’s the takeaway?
Sharing is crucial for connection, yes, but timing is everything. Imagine peeling an onion (without crying) layer by layer. Give a little, listen a lot. Connection lives in the ebb and flow, not in act-before-intermission revelations.

The “Everything’s Fine” Facade: When Dating Isn’t a Performance

Ah, the Tinder suitor who turned our candlelit dinner into an extended TED Talk about his flawless life—complete with a PowerPoint-worthy monologue about his six-figure job, his apartment with skyline views, and his twice-yearly luxury excursions to Monaco. Sounded impressive, but he forgot one crucial detail: real connection builds on vulnerability, not vanity.

Spoiler alert: people don’t date resumes; they date people. On our obligatory post-dinner walk, I couldn’t shake the feeling that I wasn’t talking to an actual person but rather an elaborate marketing brochure. It was like dating “success” packaged in a J.Crew sweater.

What’s the takeaway?
Perfection isn’t relatable—humanity is. Leave the highlight reel for Instagram Stories and bring the real you to the table. Mistakes, awkward silences, bad jokes—all of it. Besides, who wants their love story narrated by LinkedIn?

The Ghost of Past Relationships: When Baggage Isn’t Checked at the Door

Let me confess something: I once turned an innocent date into an unintentional therapy session...about my ex. There, I said it. Three dates in with someone genuinely interesting, I found myself mid-rant about how my last boyfriend “never believed in celebrating Valentine’s Day,” and without realizing it, I’d made my date a surrogate for all my unresolved gripes. The poor guy stared at me like I’d started reciting Shakespeare in Klingon.

Looking back, I now recognize what my venting actually was: an attempt to self-soothe in real-time. I wasn’t ready for a new romance—I was still overanalyzing the old one. That guy didn’t ghost me afterward, but honestly? I would’ve ghosted myself.

What’s the takeaway?
Think of unresolved baggage like vacation souvenirs—charming for you, but exhausting for anyone else carrying it. Before swiping right on a new connection, make sure your emotional carry-on is light enough to manage.

The Great Expectations: When You Forget that Love Isn’t a Checklist

Have you ever been so fixated on "what” you’re looking for that you miss out on something even better? I have. Once, in my early 20s, I made the mistake of treating dating like an Ivy League admissions process—you know, GPA equivalent, extracurriculars, personal essays, the whole nine yards. I’d drafted a mental checklist of ideal qualities my future partner had to meet (spoiler: none of it had anything to do with personality or compatibility).

Then I met someone who threw my whole checklist out the proverbial window. He was a jazz musician—not exactly "CEO material," as my naïve younger self might’ve judged—but he challenged me in ways I didn’t expect. We didn’t last forever, but thank goodness for that detour. It forced me to stop treating potential partners like job applicants and start seeing them as people.

What’s the takeaway?
Do yourself a favor and ditch The List. Sure, have your values and non-negotiables, but leave room for surprise. Sometimes the best connections aren’t checkbox-perfect—they’re deliciously unexpected.

The Julian Dating Debacle: Brooklyn Edition

Here’s a cautionary and painfully personal anecdote from yours truly. A few summers ago, I’d agreed to a casual park date with someone I met through mutual friends—a budding journalist with a seemingly endless supply of witty insights. We decided to picnic on the waterside with views of the Manhattan skyline. This already sounds romantic, right? Wrong. Very, very wrong.

First, I spilled an entire bottle of rosé, soaking my picnic blanket to the point it looked like a crime scene. Then mid-conversation, trying to impress him with an intellectual quip about Baldwin’s Giovanni’s Room, I mistakenly referred to Paris’s Left Bank as the "east side." His polite correction might as well have been a neon sign screaming “you fraud!” The final straw came when a rogue seagull dive-bombed our cheese platter. We left that park—rosé-drenched and defeated—feeling like Gotham City villains plotting retaliation against a pigeon mafia.

The postscript? Despite it all, we somehow laughed our way to a second date and even a third. Though we ultimately parted ways (amicably, folks, no pigeons were harmed), that day taught me something irreplaceable.

What’s the takeaway?
Stop trying to choreograph perfection. It’s the unexpected chaos—rosé spills and seagull invasions included—that makes dating memorable. If you’re busy chasing glossy moments, you’ll miss the genuine ones.

Take the Lessons, Leave the Regret

Here’s the truth: if you’re navigating the weird, wonderful world of dating, you’re going to trip, stumble, and occasionally fall face-first into a sea of awkwardness. But every misstep has the potential to teach you about what you want, who you are, and what truly matters in love (and life!).

So, when your next date goes sideways, take a breath. Laugh at yourself—maybe cry a little if you need to—and then ask, “What’s the lesson here?” Because if I’ve learned one thing through every mishap, mix-up, and poorly executed kiss, it’s this: love isn’t in the flawless execution—it’s in the courage to show up, try again, and embrace the glorious mess of it all.

Go forth, be bold, and remember—rosé is best served on stable ground.