The Challenge I Didn’t Think I’d Survive

Let me set the stage for you. It's a crisp fall morning in Telluride, the smell of autumn leaves hanging in the air, and I’m standing in the shadow of Wilson Peak alongside a woman I’ve just started dating. We’re chatting about something like pie crust recipes or the moral obligation to bring snacks when hiking (it's crucial, by the way), and out of nowhere, she drops a bomb:

“By the way,” she says, tightening the strap on her backpack, “I’ve never really been in a relationship before. Like, not seriously.”

Cue the sound of a record scratch in my head.

If you know anything about me, you know I'm a romantic. A sucker for long, philosophical trail chats and campfire-lit revelations. So the prospect of navigating Love 101 with someone who’s skipped the prerequisite classes? Well, let’s just say it was a challenge I didn’t think I’d survive.

Spoiler alert: I did. But not without a few metaphorical (and literal) stumbles along the way.

Unrealistic Expectations on Steroids

When we first started dating, I thought I’d stumbled into some Instagram-perfect “new love” storyline—think early scenes from a rom-com featuring a guy in flannel and a girl in hiking boots (accurate, at least for Telluride). But the reality of dating someone without much relationship experience is that no one handed them "The Rules." Not the “don’t text your ex” rules, but the practical stuff most of us learn the hard way, like how to argue productively or what it means to emotionally show up.

At first, I tried to brush off behaviors that threw me. When she ghosted me for a week after a fight over...wait for it…who claimed the last granola bar on a hike, I told myself, She’s probably soul-searching. Spoiler: She wasn't. She was hiding because she thought conflict meant the relationship was doomed.

I had wild expectations too. Somewhere between a third date and that hike toward granola-bar-gate, I decided I wanted to play the Wise Emotional Sherpa—someone who’d patiently guide her through the peaks and valleys of our relationship (pun intended). It seemed noble at the time, much like signing up for a 14er hike because it sounds romantic, only to regret it halfway up. I learned quickly that relationships don’t follow a lesson plan. They’re more “pick your path at the trailhead and hope your boots hold up.”

Lessons from Attempted "Trail Grooming"

Now, here’s where the practical part comes in. Was the journey rocky? Absolutely. Did I make some rookie mistakes of my own? Oh, you bet. But along the way, I figured out that dating someone who’s new to relationships—or frankly, new to deep emotional vulnerability—can actually teach you a lot. Here's what I learned (sometimes the hard way):

1. Lead, Don’t Lecture

On one of our early road trips, I decided to regale her with stories about my past relationships as a way to share my “deep learnings.” Classic overachiever move. I was halfway through a tale about how my ex once taught me the importance of setting boundaries when she piped up, “Wait. Is this a quiz?” And she wasn’t wrong—it felt that way.

People don’t grow because you throw advice at them—especially unsolicited relationship advice. They grow when you model behaviors that foster trust and communication. Instead of saying, “You should really just tell me how you feel,” I started saying, “Hey, I’m feeling confused about what happened earlier—can we talk about it?” The tone shift meant everything.

2. Conflict Isn’t a Catastrophe

Remember the granola bar drama? That seven-day stretch of radio silence taught me something I’ll never forget: not everyone knows how to argue and stay connected at the same time. If the idea of a fight feels like the emotional equivalent of stepping on an unmarked rattlesnake on a trail, you’ll start avoiding issues altogether. Not a healthy move.

Here’s how I reframed it in our dynamic:
- Start small: Use everyday frustrations as training ground for bigger conversations.
- Name your emotions clearly, without blame: “I felt hurt when I didn’t hear back from you,” instead of, “Why are you ignoring me?” (This one took practice.)
- Acknowledge progress! When she mastered the art of texting back within 24 hours of a minor spat, I told her how much I appreciated it. Positive reinforcement works like a charm.

Turns out, conflict doesn’t always mean someone’s hiking in the opposite direction. Sometimes it’s just detouring to find a safer path forward.

3. Expectations Should Be as Flexible as Your Hiking Socks

I learned fast that I couldn’t expect her to interpret my unspoken needs or figure out relationship “best practices” overnight. And what’s worse, I relied on this hyper-romantic notion that if she really cared, she’d just know. That’s the kind of harmful thinking that trips up even the most experienced daters.

Once I let go of the idea that she should be clairvoyant about my feelings, things changed. I’d say things like, “It makes me feel really seen when someone asks about my writing” or, “Let’s try to spend Fridays together because I like starting the weekend with you.” She didn’t always remember (spoiler: she once booked a dinner with friends on the Friday I planned picnic sandwiches #rude), but when she did? It felt intentional and real. Expectations are great—but flexibility opens up room for surprises, too.

The Humor in Surviving the “Test”

One evening, after we’d finally settled into a good rhythm, she joked, “Dating you feels like learning to drive stick shift. Sometimes I can’t even get it in gear.”

I laughed, honestly, because the feeling was mutual. I mean, this thing we were building wasn’t perfect. It wasn’t some streamlined Subaru barreling down the road of everlasting love. It was a 1980s Jeep: lots of rattles, questionable mileage, but man, when it worked, it took us to places I never thought possible.

Being in a relationship with someone who’s truly learning as they go? It’s humbling. It’s like trekking up a mountain, only to realize you’ve been so focused on the climb that you haven’t noticed the view. It’s chaotic, comedic, and deeply worth it.

Why You’re More Resilient Than You Think

I didn’t think I’d survive this challenge—and there were certainly days I questioned if I even wanted to. But here’s the thing: we all have a version of this in our relationships. Maybe it’s your partner’s inability to express their feelings; maybe it’s their tendency to retreat instead of engage. And sometimes, yeah, maybe it’s something amusingly small, like passive-aggressive granola bar etiquette. Whatever it is, the true challenge isn’t their “inexperience” or baggage or blind spots. The challenge is staying patient, being compassionate, and asking yourself: What’s worth growing through together?

Because every relationship is a trail one way or another. You can choose to turn back at the first steep incline, or you can lean into the tough parts, knowing that somewhere at the summit is a view you’ll never forget.

I wouldn’t trade those moments for anything. Not even the granola bar. (Well, maybe just one bite.)