There are moments in life when a chance encounter leaves you thinking, “I didn’t see that one coming.” For me, that moment came on a sultry late-summer evening in Sedona, where the red rocks glow like embers at sunset and everyone seems a little more spiritually tuned in than you are.

The Evening That Turned Left

I was nursing a lukewarm iced coffee at one of those artsy outdoor markets—think dreamcatchers for sale, acoustic guitarists strumming John Mayer covers, and at least three people named Serenity running vendor tables. As the golden hour painted everything in rich, warm tones, I noticed an older man sitting at the edge of a courtyard fountain, feeding pieces of granola bar to a crow perched on his shoulder like something out of a Wes Anderson film.

I’m not one to strike up conversations with strangers (I like to blame the digital age, but honestly, I’ve been this way since AIM chats took up all my social batteries). Something about the man—the cowboy hat, the faded turquoise bolo tie, the aura of “I know more than you, kid”—caught my attention. Before I knew it, I was asking him about the bird.

“It’s not about feeding the crow,” he said without missing a beat. “It’s about showing up for what shows up.”

Now, I know what you're thinking. That sounds like something you'd see printed on a Lululemon tote bag or a desert-themed Pinterest board. But in that moment, his words sank in like a rock thrown straight into the still water of my overthinking mind. Show up for what shows up.

Lessons from the Leather-Worn Philosopher

We didn’t part ways with just one philosophical soundbite either. As we chatted, I learned his name was Grant, a retired park ranger who now spent his time hiking, making art from found objects, and connecting with people “letting life happen to them rather than living it.” He pointed out that most people, especially in relationships, are stuck trying to control the outcome before they’ve paid attention to what’s actually happening.

Grant wasn’t wrong. I’d spent plenty of time in relationships curating the perfect moments—multi-course date nights planned with military precision, surprise trips designed to impress, and conversations engineered to elicit the exact responses I thought I wanted. And somehow, the more effort I put into controlling the narrative, the harder it was to connect genuinely.

“You’re grasping, not engaging,” he said, casually handing the crow another tiny granola square. And yeah, I winced. It reminded me of trying to get someone to love you while presenting a version of yourself you think they’ll adore. Sure, it works for a while, but eventually, it’s like trying to hang on to sand by squeezing your fist tighter.

How This Applies to the Rest of Us Mortals

So, how do you step away from grasping and start truly engaging, both in romantic relationships and in life? Grant’s advice stays with me, and it’s surprisingly applicable whether you're on a first date or 15 years deep with someone. Here’s how I’ve adapted his words into practical takeaways:

1. Stop Overplanning

Take it from a recovering overachiever—you don’t need to outline your personality like you're pitching a TED Talk. Be present instead of trying to showcase the highlight reel. I’ve found that the most meaningful moments in dating or relationships often come when you ditch the itinerary. You don't need to be the human equivalent of a five-star Yelp review.

2. Get Comfortable with Silence

We treat silence in conversations like it’s a ticking time bomb, rushing to fill it with the first thing that comes to mind. But Grant sat quietly with me for long stretches and made me realize it’s okay to let the air breathe. Turns out, not every interaction requires a drumroll of banter to feel authentic.

3. Offer Without Expecting

If you’ve ever gone out of your way to do something nice for someone and instantly craved validation, well, same. Grant reminded me there’s peace in giving of yourself without expecting a transactional payoff. Whether it’s listening without waiting to pounce in with advice or simply showing up and being vulnerable, you’ll win by focusing on the process rather than the reward.

4. Trust the Unscripted

At one point, I asked Grant how he handled setbacks in life. He laughed and said, “Kid, I hike a lot of trails, and the best ones don’t have mile markers.” Translation? Life (and dating) tends to get better when you stop sticking so closely to narratives—or to that person's "dream partner checklist" they swore made sense when they wrote it in their Notes app at 3 a.m.

A Quieter, More Honest Connection

After that day, I went on to date someone whose energy matched the grounded vibe Grant exuded—someone I could be real with, cracks and all. Our dates weren’t perfect, but they were honest. We eventually broke up (plot twist: he got a job offer in Seattle and fell for someone in his cycling group—ouch), but what stuck with me was a lesson learned from Grant: showing up fully for someone is about letting them meet you where you are, not where you wish they'd find you.

So, Maybe Take a Walk—Or Feed a Crow

We spend so much time chasing perfection: the flawless Instagram grid, the meet-cute that rivals “When Harry Met Sally,” the idea that a relationship is only as good as the metrics we assign to it. But when you strip away the noise and the game plans, what you're left with is the connection you’re willing to nurture. And in my case, a wise stranger taught me that sometimes, the richest bonds come when you stop trying so hard and “show up for what shows up.”

Whether you’re flirting with someone new or carrying the weight of long-term love, it turns out the cowboy at the fountain—and his crow—was right all along: Being present beats perfect, every time.