The Lessons I Wish I Knew Earlier
The Flirting Disaster That Taught Me Timing is Everything
There I was, standing under the neon glow of a boardwalk arcade, stomach doing flips like I’d just stepped off a Tilt-A-Whirl, gathering the courage to talk to a boy who worked the skee-ball counter. I had rehearsed my opening line (something about how impressive his ticket-counting skills were—it sounded better in my head). But by the time I actually walked up, he had already turned to help another customer.
Lesson learned: timing is everything. Whether it’s a casual flirtation over funnel cakes or confessing feelings that’ve bubbled up like a shaken can of Coke, rushing in—or holding back too long—can spell disaster. The key? Tuning into the other person’s signals. Pay attention to the ebb and flow of conversation, body language, or the occasional awkward pause. Trust me, it works better than clunky attempts to force a vibe in the wrong moment.
Stop Playing the Compatibility Chameleon
In college, I went on exactly two dates with someone whose favorite activity was debating the finer points of Civil War history. Suddenly, I was brushing up on battle strategies and pretending I had strong feelings about General Sherman. (I did not.) I wanted to be the “right” person for him—but guess how much fun I had, pretending to care about fortifications at Gettysburg? About as much as I’d have rooting for sandcastles to survive high tide.
Lesson learned: being someone you’re not for the sake of connection is exhausting — and unsustainable. Instead of being a human mirror, I’ve found more success showing up as my unfiltered self. Sure, it’s terrifying to admit you’d rather binge 90s romantic comedies than debate the past century, but it’s also liberating. If you can’t connect as you, then why bother? Life’s too short for midnight Google searches to fake expertise in things you secretly find boring.
Kindness Isn’t Flirting, and Flirting Isn’t a Contract
Here’s a hard truth my 20-year-old self could have used: just because someone is nice to you doesn’t automatically mean they’re romantically interested, and just because you flirt doesn’t mean you owe someone a thing. That one took me a while to sort out. Cue one very confusing summer when a barista at my favorite beachside café gave me extra whipped cream on my iced latte — twice! I thought for sure it meant something. (Spoiler: it didn’t. He was just kind!)
Lesson learned: context and intention matter. Building connections can be nuanced, and learning to read those nuances (without jumping to wishful conclusions) can save a world of heartache or awkwardness. Similarly, when I’ve been the one casually flirting for sport, I’ve had to remind both myself and others—playful words don’t entangle you in lifelong obligations. Clear intention is what makes the difference.
Choose Chemistry and Values
I used to think chemistry was a shiny, all-powerful force that could override other hiccups. That intense spark? It had to mean something, right? Wrong. There was a guy I went on a date with—let’s call him “Ben.” The banter was electric, sparks flying like fireworks on the Fourth of July. But guess what? Our values? Barely aligned. Conversations veered into territory that made my stomach churn, but I ignored it because hey, we had “chemistry.”
Lesson learned: chemistry isn’t enough on its own. I wouldn’t walk barefoot over seashells for anyone who didn’t share the building blocks that really mattered—respect, honesty, and the willingness to understand the other person’s worldview. Sure, it’s thrilling to feel fireworks, but lasting love isn’t built on pyrotechnics alone. Sustained warmth? That’s the real gold.
Embrace the Awkward
If there’s one universal truth of relationships, it’s this: things will get awkward. Whether you’re fumbling for the “right” thing to say after misreading a situation or you’re trying to decipher if your date meant to touch your arm or just spilled their drink, humans aren’t smooth 100% of the time (despite what Hollywood rom-com montages make it seem like).
Once, I knocked over an entire plate of oysters on a first date. I froze, cheeks burning, convinced I’d just ruined everything with my (very expensive) spill. But to my surprise, instead of making a big fuss, my date helped me clean it up—and we laughed about it later. That small moment actually brought us closer because we got to see each other as real, fallible people.
Lesson learned: awkwardness isn’t your enemy—it’s part of being human. If you’re too busy trying to engineer “perfect,” you’ll miss the magic in moments where you’re just you—oyster spills and all.
Don’t Fall for Potential
This one’s a doozy. I spent years falling not for who someone was, but for who I thought they could be. I’d cling to the imagined future version of them—when they’d figure out their career, dial down their temper, or miraculously develop great communication skills—while excusing all the red flags blinking like a lifeguard’s safety warning.
Lesson learned: date the person standing in front of you, not their hypothetical glow-up. It’s one thing to grow together in healthy ways, but crossing your fingers that they’ll magically evolve into Mr. or Ms. Right isn’t realistic—or fair. Now, I ask myself: “If nothing about this person changed, would I still be happy?” If the answer’s no, I don’t try to force it.
Keep a Little Life Outside of Love
I once knew someone (okay, it was me) who built her entire world around a new relationship. We’d hang by the shore, watch movies under string lights on my patio, and take Sunday bike rides to our favorite sandwich shop. Sounds idyllic, right? Well, it came to a screeching halt the moment things ended. My own interests? Shelved. Time for friends? Neglected. And when the relationship fizzled, I had no idea who I was without it.
Lesson learned: balance matters. Keeping hobbies, friendships, and passions beyond your relationship is key—not just as a fall-back plan, but because you’re a whole person, not just half of a couple. Love is sweet, but so is knowing how to fill your days with things that light you up, even if romance isn’t in the picture.
You’re Not on a Deadline
Finally, the single biggest revelation I wish I’d heard sooner: there’s no expiration date on love, connection, or finding your person (or people). A lot of dating pressure comes from this self-imposed (or society-imposed) sense that you’ve somehow “fallen behind.” The truth? There’s no rulebook. People find love at 22, 42, or even 72. Timing isn’t your enemy, and life unfolds differently for everyone.
Lesson learned: the idea of being “behind” only exists if you buy into it. You’re not racing anyone, and the journey of discovering meaningful connections—romantic or otherwise—is one that unfolds in its own time. Honestly, I’m learning to savor the “in-between” stages too, because every chapter, even the awkward or lonely ones, teaches you something valuable.
Final Takeaway:
Relationships are beautifully messy, hilariously unpredictable, and endlessly illuminating. We don’t get handed an instruction manual at birth, but with every stumble, awkward conversation, or lesson learned, we become a little wiser about what matters most. Whether you're swiping seashells off your porch mid-date or figuring out whether the person in front of you is the one—or just someone—you’re collecting tools for your next adventure.
So here’s to diving in—awkward spills and all—and trusting that every step teaches you something worthwhile. You’ve got this.
