The Art of Overthinking: How My Obsessions Shape My Relationships

We all have that one friend who can’t sit through a movie without IMDB-ing every actor’s life story or someone who spends an unsettling amount of time curating Spotify playlists “for every conceivable mood.” Spoiler alert: I am that friend. My particular brand of obsession is best described as “low-stakes perfectionism.” I will happily spend an entire Saturday trying to unlock the exact method to get crispy edges on pancakes (cast iron, slightly overripe bananas, and patience, for the record). Or I’ll wander through several aisles of REI looking for the perfect moisture-wicking hiking socks.

Whimsical? Maybe. Exhausting? Definitely—but only for people trapped in Costco with me as I weigh the pros and cons of different trail mixes. What started as a personal quirk, though, has proven to be profound in my larger relationships. My obsessions show up in how I connect with people and, often enough, how I complicate that connection. Let’s unpack this, shall we?

The Pancake Principle: Obsessing Over the Little Things

Confession time: Sometimes I struggle with being present in my relationships because I’m laser-focused on small, often inconsequential details. This isn’t necessarily a bad thing. My friends know they’ll never get a crumbly, mediocre pancake when breakfast is at my place. (It’s always fluffy with golden edges or bust.) But it can pose a problem when I prioritize “perfect execution” over actual interaction.

Let me paint you a picture. A while back, I hosted brunch for a couple I’d just started to get to know. As they sat chatting in the living room, I was in the kitchen, meticulously pouring pancake batter in geometrically precise circles, heat adjusted to within an inch of its life. I missed half their conversation because I was zealously wielding a spatula like I was on an episode of Top Chef.

One of them, bless her, eventually strolled into the kitchen and said, “You know, we’re more interested in hanging out with you than your pancakes.” It was a humbling—and slightly mortifying—moment of clarity. My obsession with execution had eclipsed the reason I was flipping those dang pancakes in the first place: to connect.

Lesson learned: Perfection doesn’t always foster connection. Sometimes they’re happier with your slightly messy, slightly burnt pancakes if it means you’re fully present while they’re eating them.

Passion as a Love Language: Is Trail Mix Romantic?

Not long ago, a hike in Utah's glorious Zion National Park served as the backdrop for an unexpected dating lesson. I had painstakingly assembled the ultimate trail mix for the outing—pecans because they’re buttery, dried cherries for sharp sweetness, dark chocolate chunks because life is short, and a whisper of sea salt to tie it all together. Yes, I thought I was a genius.

About halfway through the hike, I whipped the bag out of my backpack, triumphantly offering it to my date. He looked at the bag with a mix of confusion and horror. “No pretzels?” he asked. Turns out, he was a die-hard pretzel kind of guy, and I’d failed to account for this in my utterly unnecessary three-hour trail mix experiment. Cue me spiraling into an internal monologue: Why didn’t I ask about his snack preferences? What does it say about us that his ideal mix is my snack kryptonite? Should I have known this sooner?!

The thing about my obsessions is they’re often tangled up in the way I show affection. Curating the perfect trail mix wasn’t about impressing him (okay, maybe it was a little); it was about showing that I cared. What I missed in the process was the more valuable opportunity to have asked, “Hey, what’s the snack that makes you happiest out here?”

Lesson learned: Genuine connection doesn’t always come from obsessing over what you think is perfect for someone—it grows when you make room for what they consider meaningful, even if it's (sigh) pretzels.

The IMDB of Human Interaction: Overanalyzing the Non-Verbal Narratives

Here’s another fun way my obsessions manifest: decoding subtext. I’m the person who replays conversations in my head like a Sherlock episode, zooming in on tone shifts and body language clues, hunting for the emotional equivalent of invisible footprints. Did he pause a little before saying “I’m fine”? Did she use a lot of ellipses in her last text? Is the polite laugh the same as the “let’s just be friends” laugh?

This obsessive decoding comes from a good place—I genuinely want to understand the people I care about. It’s my way of closing the gap between what’s said and what’s felt. But I’ve learned that, in practice, this can be equal parts insightful and completely maddening—for me and everyone else involved.

One evening, after a particularly frustrating volley of texts with someone I was dating, I finally confessed my overanalysis. “I feel like I’m looking for answers you haven’t given me, and it’s making me weird,” I told him. His response? “Caleb, just ask me what you’re feeling too awkward to ask outright.”

Mind-blowing, I know. Turns out, asking him directly was WAY more productive than mentally cataloging punctuation marks for hidden angst.

Lesson learned: Relationships aren’t escape rooms. You don’t have to crack every emotional code—sometimes it’s okay to just open the door and, you know, communicate.

Obsessions as Connection Superpowers

Here’s the thing: My obsessions aren’t just quirks—they’re tools. When channeled the right way, they make me curious, attentive, and deeply invested in my relationships. They remind me to pay attention to details, like learning your favorite tea or remembering you bench-watched The Great British Baking Show during flu season. They make me pause during a sunset hike to snap photos, not just for Instagram (#viewsfordays) but because I want to remember what it felt like to share the moment with you.

But they also teach me balance. Not every pancake needs to be photogenic. Perfection in trail-mix form is a myth. And sometimes, clarity comes faster when you stop decoding and just ask.

Takeaway Thoughts for the (Fellow) Overthinkers

So, to all my fellow overthinkers and obsessive hobbyists out there: Lean into your quirks. They’re a part of what makes you endlessly interesting and uniquely lovable. But remember that the people who care about you aren’t evaluating you on your pancake consistency or your Spotify playlist sequencing. They just want you—slightly crispy edges and all.

Focus less on getting everything “right” and more on simply showing up. Because connections aren’t built on perfect pancakes or trail mixes—they’re built by the simple, messy, beautiful art of being present. And if you can do that with a killer snack in tow? Well, that’s just the (caramel) drizzle on top.