Lessons I Wish I Knew Earlier

Let me paint you a picture: I’m twenty-three, sitting at a steakhouse bar in Phoenix wearing a shirt so loud it could double as a lifeguard. Across from me is my date. She exudes cool, slicing her filet mignon with precision, and I’m awkwardly yammering about desert architecture like I’ve got a TED Talk on the subject. She smiles politely. Inside, I’m already shrinking into a cactus of embarrassment.

The lesson I didn’t know yet? Being yourself is only good advice when you actually know yourself. At the time, I was playing a version of “dateable me” I thought would work, rather than showing up as my messy, desert-dwelling, Ansel Adams-loving, modern-country-daydreaming self. Mistakes were made—but hey, they’re now stories worth sharing, which I plan to do here.

This is your permission slip to sidestep some potholes I stepped directly into, cowboy boots and all. Let’s dig in.

1. Don’t Date the Highlight Reel (Theirs or Yours!)

We’re all guilty of putting on a good show, and first dates are prime time for this. You share your greatest hits, gloss over the mishaps, and hope no one notices you reheated last night’s confidence leftovers just to make it through. The problem? Glossy façades are about as stable as a sandcastle in monsoon season.

In one ill-fated case, I committed my own highlight-reel sin. I “leaned in” to interests I thought would impress, rattling off fancy craft whiskey trivia like I moonlighted at a distillery. Spoiler alert: My date was sober. We never made it to dessert. The takeaway? Build real connections from a base of mutual truth, not a résumé of personality. Be curious about who someone really is—and show up as your authentic self, not the Instagram-filtered version.

2. Timing is Everything (Know When to Pivot)

Here’s a cold, hard desert truth: Some relationships fizzle, and that’s okay. The secret is knowing when.

Picture the Arizona desert in late July—you’re 20 miles into a hike with no water left, pretending you’re fine because backtracking feels like defeat. That’s what I did once in a relationship that had clearly run its course. We both stuck it out for far too long, convincing ourselves there was an oasis just over the horizon. Spoiler again: There wasn’t.

Lesson learned? Listen closely to what the dynamic is telling you. Relationships are not endurance tests—they’re a shared journey. And sometimes, calling it quits means saving space for something better. Remember, progress isn’t about stubbornly moving forward but about moving forward wisely.

3. The Myth of the “Perfect First Impression”

Raise your hand if you’ve ever spiraled over the perfect opening line, outfit, or venue. (I’d raise mine, but it’s currently holding a tumbler of iced tea—a desert necessity.) It’s natural to want to start strong, but here’s the twist: Authenticity trumps perfection every single time.

When I was 29, I went on a truly awful first date—awkward silences, mismatched energy, the works. Worse, my nerves had me mispronouncing risotto as if it were a foreign currency. Mortifying. But somewhere in that mess, my self-conscious laugh broke the ice. We started making fun of ourselves, and suddenly, it wasn’t about being “perfect.” It was about being human. That date turned into three years of something great.

Your quirks aren’t dealbreakers; they’re mile markers for the right people. Let the real you be the handshake that welcomes them in.

4. Learn to Spot the Signal Within the Noise

This one took me far too long to figure out: Just because someone likes you doesn’t mean they’re good for you. Love on its own is not a magic aloe vera plant that fixes everything.

When I was 26, I dated someone who sent my heart racing but also constantly drained my emotional batteries. She loved the idea of me—southwestern sunsets, career ambitions, neat Desert Modern design tastes—but wasn’t particularly interested in the messy, human details. Any conversations about genuine needs or compromises? Forget it. It took me ages to decipher the difference between initial spark (fun but fleeting) and true compatibility (less dramatic but far more sustainable).

If someone’s energy doesn’t leave you feeling safe and valued, pivot like a golf cart to a smoother course. Chemistry’s fun, but connection is built on care and effort.

5. Invest in Yourself First (Think of It as Desert Landscaping)

Have you ever tried planting a garden in the Sonoran Desert? It takes insane effort. You map sunlight, choose hardy plants, and water consistently. Your investment pays off in bursts of blooms as vibrant as Sedona’s red rocks. Guess what? You’re the garden. Your most fulfilling relationships will spring from the time and care you give yourself first.

When my career took off in marketing, I went through a phase where work replaced personal growth. I thought if I could be “successful,” I’d automatically show up as someone worth dating. Turns out, they don’t hand out Best Partner awards for exhaustion and neglecting your emotional health. Go figure.

When I shifted gears—focused on therapy, hobbies, and those nostalgic desert hikes—I started to actually enjoy myself, single or not. By the time I ended up in a healthy relationship, I was firmly rooted in who I was.

So, plant the seeds now: take up an interest that fills you with joy, address the insecurities you’ve been avoiding, and figure out what you need before someone else is in the mix.

6. Celebrate the Weird Stuff

Here’s a deeply unromantic confession: I have an extensive collection of vintage Arizona postcards framed in my living room, and I belt “Heartache Medication” by Jon Pardi a bit too enthusiastically on road trips. Past me might have downplayed these quirks on dates, especially with someone who made me feel like I needed to “chill.” Today? I couldn’t care less, because those are the quirks that made my current partner laugh until they cried.

Lean into your weirdness. Love isn’t about shaving off your edges; it’s about finding someone who loves the way they catch sunsets. Seriously, life’s too short for boring. Own the things that make you unique—the right person will see them as treasures, not inconveniences.

Final Thoughts: Give Yourself Grace

If you’re cringing at your past mistakes, congratulations: You’re perfectly human. Look, dating is wild. It’s unpredictable and, at times, as frustrating as trying to fold an oversized map in the middle of a desert gust. But, like any good hike, it’ll teach you a lot if you let it. Every step matters—even the ones where you trip over a metaphorical cactus and spend the next hour plucking out the needles.

Own where you’ve been, stay curious about where you’re going, and don’t forget to enjoy the scenery along the way. You’ve got this—and if nothing else, you’ll have some top-tier stories to share when all is said and done.

Oh, and for the record, don’t sweat it if you butcher a fancy menu word. Life’s too short for perfect pronunciations anyway.