When Love Gets Messy: Lessons From Relationships That Went Awry

We all enter relationships with the best of intentions. Maybe you thought your “artist dating an artist” dream would rival Frida Kahlo and Diego Rivera (minus, you know, their drama). Or maybe you swore that opposites—like your outdoorsy self and their steadfast aversion to sunlight—would attract. But life, love, and human beings are unpredictable by nature. Sometimes, things burn hot and fizzle fast. Sometimes, they blow up spectacularly, leaving you with nothing but a playlist you can’t listen to anymore. But here’s the good news: even when things go sideways, you learn. Here are some unforgettable lessons from people who've navigated relational chaos—and maybe made it out a little wiser on the other side.

1. Check Your Expectations at the Door—They Tend to Overpack.

Truth time: we all bring a carry-on full of dreams (okay, baggage) into relationships. When I was 25, fresh out of college and buzzing on Santa Fe sunsets and Rumi quotes, I thought love meant lightning. I dove headfirst into a relationship with Ezra, this brooding sculptor who smelled like cedarwood and questioned capitalism at every turn. It was fiery, dramatic, and—unsurprisingly—a little unsustainable.

Turns out, fiery sculptors tend to come with some... ripped canvases of their own. We both expected our passionate dynamic to nourish us endlessly without realizing it also drained us. If you find yourself tiptoeing around what you need because fulfilling their poetic angst feels like a full-time job, pause.

Lesson learned: romance isn’t a do-it-all vending machine. Pack light, and talk often about what’s realistic versus an idealized Pinterest board version of love.

2. Chemistry Is Great, But Don’t Skip the Compatibility Test.

Remember the time you swore that collecting houseplants could totally coexist with their aggressively minimalist approach to living? Or the time I brought a boyfriend to my parents’ gallery opening only for him to dismiss the Southwest art scene as bourgeois nonsense after two glasses of muscat? (Yeah, it was a long drive home.)

Here’s the thing: sparks and butterflies are fun, but shared values—not just hobbies or Netflix preferences—make a relationship thrive. Chemistry might get your foot in the door, but compatibility brings furniture for the long haul. Are they someone you can grow with? Do their habits, hopes, and quirks feel like pieces of the same puzzle—or just shaping up to be a thousand-piece picture of chaos?

A quick internal inventory of your non-negotiables helps clarify what really matters. Hate confrontation? Dating a “tell-it-like-it-is” type might not be the most peaceful pairing. Love having deep, 2 a.m. conversations under the stars? Someone who avoids emotions like they’re on fire might not be a desert rose fit for your vibe.

3. Mistaking Red Flags for a Vibe Is Easier Than You Think.

“Doesn’t initiate plans = they’re just a free spirit.” “Unsupportive of your goals = they don’t get capitalism either.” Literally everyone I know (myself included) has tried to squint optimistically at neon red flags until it felt acceptable to call them mood lighting. It’s human! We want love to work.

There was the time I dated a guy who thought the concept of “checking in” was suffocating. At first, I chalked it up to his adventurous, bohemian energy: “Wow, he’s so chill! I need to be less clingy!” Spoiler alert: what felt like dreamy spontaneity in month one turned into frequent cancellations at month six and a whole lot of solitude for yours truly.

Here’s a hack: write down what you’re noticing. Seriously, pen to paper. Sometimes reading something like “stopped replying to texts for three days after a minor disagreement” will help you go, “Oh, hold on, that’s just a bad habit—we’re not romanticizing this anymore.”

4. Breakups Can Break You Open—in the Best Way.

When a relationship ends, it’s easy to feel like you’re watching the credits roll on a movie you really wanted to love. But endings can also feel liberating, clarifying, even transformative. There’s something powerful about letting go of something (or someone) that wasn’t really serving either of you.

After Ezra and I called it quits, I was shattered—and then... I wasn’t. I realized I’d spent so much time trying to be the perfect supportive partner that I’d forgotten to nurture the artist in me. It was like finding a neglected corner of my soul, dusting it off, and thinking, Oh wow, I’ve missed you.

Real talk: breakups don’t have to feel like failures. Think of them as transitions, like the stark beauty of a winter sunrise in the desert—a little chilling, but still vibrant and full of life to come.

5. Communication Isn’t Sexy, But It’s the Secret Sauce.

Before my parents opened their gallery each morning, they’d go through every detail—lighting, pricing, even the placement of that one polarizing turquoise sculpture. They didn’t leave much to chance. And while gallery logistics aren’t the same as romance, the principle stands: intentional communication creates harmony.

In relationships, though, it’s tempting to avoid the hard stuff. You think, This brunch is too nice to discuss merging finances, or, Why ruin a perfectly good Saturday with a fight about whose turn it is to plan date night? Spoiler: avoiding necessary conversations doesn’t avoid the issue—it just delays emotional clutter.

Instead of viewing tough conversations as dark clouds, treat them like spring rain: a little uncomfortable at first, but what blooms after will make the discomfort worthwhile. Whether it’s unmet expectations or conflicting feelings, say the thing. Trust me, unspoken tension is way less romantic than a clear, awkwardly vulnerable heart-to-heart.

6. Find the Balance Between Effort and Effortlessness.

Okay, let’s play with a metaphor. Imagine love as a landscape. Some days, it’s a postcard-perfect meadow—light, breezy, effortless. Other days, it feels more like trekking up a canyon: breathtaking in its challenge, worth every step, but not exactly casual. What it shouldn’t feel like? Digging through volcanic rock with a spoon.

In the healthiest relationships I’ve known—whether my parents’ steady partnership or my best friend Lucy’s marriage—there’s a rhythm of give and take. Sure, they put in effort, but it’s never one person doing all the heavy lifting while the other kicks back and watches. If you’re the one constantly “fixing,” giving, guilt-compromising, or compensating, it’s time to examine whether the dynamic is tipping past sustainable.

7. You’re Allowed to Want Something Extraordinary.

I used to feel embarrassed about how much I romanticized love. Like, how dare I expect anything more than coffee dates and vaguely lukewarm companionship? But the truth is, romanticizing isn’t bad—it’s human. It shows you’re invested in connection, in meaning, in something more than perfunctory dating.

Here’s the secret: extraordinary love—healthy, uplifting, fulfilling—isn’t perfect. It’s not Instagrammable montages or scripted grand gestures. It’s that quiet understanding when you’re disagreeing during a road trip, or them showing up with your favorite sopaipillas when you’re sick. It’s patient and grounded but still alive, surprising, and worth holding on to.

Final Thoughts

When relationships get messy—or end entirely—it can be easy to fall into a spiral of regret, replaying the “if onlys.” But each relationship you’ve had plays a role in shaping how you love, what you value, and how you view yourself.

If there’s one thing Santa Fe—and relationships—has taught me, it’s that beauty often lies somewhere between chaos and stillness. Art isn’t about perfection; it’s about transformation. Relationships are the same. Whether they bloom into something dazzling or fizzle into life lessons, every chapter carries value.

So here’s to the lessons, the honesty, and the extraordinary connection you're brave enough to keep reaching for. Better days? They’re coming, desert sage.