Lessons I Wish I Knew Earlier

There’s something about hindsight that makes us all feel like we have a crystal ball we were too busy ignoring. I’ve had my fair share of moments where I’ve wanted to grab my younger self by the shoulders and say, “You’re really going to wear that to meet his parents?” So today, I’m opening my little vault of lessons—the personal, awkward, and occasionally wise-to-help you dodge a few pitfalls or, at the very least, feel less alone when you step into them yourself.

1. It’s Okay to Be Unapologetically Weird

In my early twenties, I tried hard to downplay pieces of myself to make relationships feel smoother. I avoided talking about my obsession with tidepool ecosystems after a guy once joked, “Wow, sounds like you really love seaweed.” I even hid my Rachel Carson quotes collection like it was some sort of shameful diary. But do you know what happens when you act like a muted, diluted version of yourself? You attract people who love a muted, diluted version of you.

Fast forward a few years, and my now-partner not only tolerates my nerdy rants about barnacles but actively takes notes so he can keep up. The point is, letting people see your quirks—the ones that make you want to curl into a hermit crab shell—is like creating a lighthouse for the right kind of people. If they’re scared off by your beacon, they were never going to make it through the fog anyway.

2. Red Flags Aren’t Handy Crafts—Don’t Try To “Fix” Them

Oh, past me. You sweet, misguided fixer-upper enthusiast. A lesson I wish I’d learned during the time I stayed with someone whose idea of vulnerability was admitting he didn’t recycle: people reveal themselves early. Listen closely.

Instead, I wasted weeks of my life convincing myself I was the kind of person who could “help” others rise to their potential. Spoiler: You can’t. Maybe you will for a short time, but it’s exhausting, frustrating, and—more often than not—the result of seeing what you hope someone could become rather than who they are.

Real love isn’t a project. It’s two whole, flawed but willing people meeting as they are and deciding “Yep, I like you with all the metaphorical barnacles intact.” If someone’s red flags read like a United Nations summit of warning signals, that’s a sign to exit gracefully, not an invitation to play emotional therapist.

3. "Should" Is the Most Dangerous Word in Dating

“I should want to date someone like him.”
“We should be taking the next step.”
“This relationship should feel easier.”

If I had a dollar for every time I used the word “should” as a relationship compass, I’d be relaxing on a sailboat off the Maine coast with a thermos of clam chowder right now. (If you haven’t eaten soup while wrapped in ocean spray, what are you even doing?)

The truth is, we’re bombarded by cultural expectations and rom-com plotlines telling us how things are supposed to go: by X age, we’ll meet the one, feel fireworks, and synchronize our playlists forever. But dating—and relationships—are wonderfully, painfully, messily individual. You can’t shoehorn your experience into someone else’s script.

So the next time you catch yourself spiraling into “should,” pause. Hold up that idea like you’d inspect a misleading trail map in Acadia—does it serve you? Or is it leading you straight into a swamp of unmet expectations?

4. Awkward Moments Make the Best Stories

I once went on a date that began with a kayak rental and ended with both of us capsizing into the Atlantic. Add to the scene a very wet lobster trap, several aggressive seagulls, and me losing an oar mid-panic. It wasn’t the love story of a lifetime, but it was laugh-out-loud funny when I recounted it to my friends later that week.

Here’s the thing: dating is inherently awkward. Even those picture-perfect couples you envy probably have a first-date mishap where one of them spilled spaghetti on the other. It’s all part of the process. Instead of dreading these moments, lean into them. Keep a sense of humor; embrace the cringy charm of it all. It’s these stories that make the journey richer, even when the relationship doesn’t last. Bonus: you’ll entertain your friends at every brunch for years.

5. The Right Person Feels Like Low Tide, Not a Storm

Look, I love a good thunderstorm along the coastline—the kind that makes waves crash in a wild, electric way. But here’s what I’ve learned about love: the thrill of chaos fades, and what you’re left with matters much more.

The relationships I used to chase felt like hurricanes—intense and dramatic but utterly exhausting. Meanwhile, the most beautiful loves are subtle, like Maine’s low tide: peaceful spaces where everything feels unhurried, comfortable, and…possible. There should be room to breathe—not constant jolts of intensity screaming prove your love or else. A lasting connection isn’t something you gut out every mile of; it’s something that feels ever-present and solid, like the bedrock beneath the waves.

So if the chemistry isn’t a fireworks show? That’s okay. Fireworks are noisy and brief. Look for shared sunsets, calm waters, and conversations you don’t want to end.

6. Love Doesn’t Make You; It Grows With You

Back in college, I was under the impression that finding The Right Partner™ would be akin to solving a puzzle. I naively thought, “Oh, they’ll complete me, and then voilà, I’ll become perfect.” Turns out, love isn’t a magic spell that fixes everything; it’s the soil you plant in while you’re actively rooting for your own growth.

Good relationships don’t erase your baggage or magically turn you into a person who can touch raw oysters without cringing—it’s all about choosing to grow alongside someone who’s also putting in the effort. Spend time nurturing yourself (yes, this means everything from solo hikes to therapy), and you’ll be better equipped to give and receive love. After all, you can’t pour from an empty coffee pot—and hopefully, yours is filled with something rich, smooth, and ideally caffeinated.

7. It’s Never Too Late to Pivot

For years, I clung to the idea that relationships should have definitive timelines. I stayed in mismatched relationships far past their expiration date because of sunken costs—like I’d already invested so much time, so I had to make it work.

But here’s what I wish I’d understood: leaving doesn’t mean you failed; it means you’ve decided you deserve more. Whether it’s a lackluster romance, a toxic partner, or simply a sparkless connection, you owe it to yourself to pivot. Life, like Maine’s coastal trails, often requires you to change direction. Sometimes the most beautiful views are hidden until you take that sharp left turn.

The Takeaway: Rewrite the Script as You Go

If I could go back and leave my younger self a trailhead signpost, it would read: “This isn’t linear, and that’s okay.” Love, dating, and building meaningful relationships are rarely a straight path from point A to happily ever after. But along the way, you’ll pick up lessons that shape you, funny memories that help you laugh at the missteps, and clarity about who you are and what you need.

So be bold. Be awkward, honest, and impossibly yourself. Let the wrong people come and go like ocean tides—and trust that the right ones will stay like the granite cliffs of Mount Desert Island: steady, weathered, and spectacularly worth it.