Let me tell you a little secret about wisdom: it tends to show up late to the party, like that friend who misses dinner but arrives just in time for dessert. I’ve had my fair share of “If only I’d known” moments, especially when it comes to relationships. And while hindsight has 20/20 vision, we don’t always need to learn things the hard way. Sometimes, someone else’s hard-earned lessons—ahem, mine—can save you the trouble. So pull up a chair (or a patch of grass if you’re into that outdoors vibe), and let me share a few lessons I wish I’d gotten the memo on earlier.

1. You Can’t Skip Chapters

Here’s the thing about relationships: they’re not Netflix shows. You don’t get to fast-forward past “the awkward getting-to-know-you phase” to skip straight to “the heartfelt montage with soft indie music playing in the background.” It doesn’t work that way. And honestly? It shouldn’t.

I used to think that if a relationship felt tricky or uncertain at the start, that meant we weren’t “right” for each other. Spoiler alert: that’s not how connections work. Real relationships, like great hiking trails, often have switchbacks and rocky patches. What matters is whether two people can navigate them together.

The best relationships are built in layers—trust, vulnerability, inside jokes about who spills more pancake batter on Sunday mornings (it’s me). You can’t rush those moments. Take your time. Let it unfold, even if it feels messy. It’s worth it.

2. Compatibility Isn’t About Sameness

Once, on a warm summer day in Tahoe, I tried dating someone who was entirely me but in a different body. She loved folk music, could build a campfire in her sleep, and had strong opinions about the best brand of hiking boots. On paper, we seemed perfect. In reality? We were more “roommates with overlapping Spotify playlists” than partners.

Here’s what I’ve learned: compatibility isn’t about liking all the same things. It’s about how your differences complement each other. Are you more of a spontaneous dirt-road detour kind of person, while your partner meticulously plans road trips? Great. That balance can make life richer. Relationships thrive when there’s enough overlap to connect you and enough contrast to keep things interesting.

3. Boundaries Are Sexy (No, Really)

If young, overly-earnest Trent had met current Trent, I would’ve pulled him aside and gone, “Listen, buddy, stop saying ‘yes’ to everything.” Back then, I thought being agreeable was the key to making someone happy, so I bent over backward more often than a yoga instructor.

The truth is, setting boundaries isn’t about saying “no” for the sake of it; it’s about knowing your limits and communicating them. It’s saying, “This is what I need to feel respected and seen,” and allowing your partner to do the same. When both people show up with clarity about their emotional and personal space, respect deepens—and honestly, nothing is more attractive than mutual respect.

So protect your weeknight solo movie tradition or your insistence that peanut butter doesn’t belong on pancakes (don’t @ me). Boundaries = care.

4. Grand Gestures Are Overrated

Movies lie. Yep, I said it. You don’t need boomboxes held aloft in pouring rain or deeply choreographed flash mobs to show someone you care. Real love? It’s quieter, and thank goodness for that.

It’s in noticing how your partner’s voice lilted differently after a hard day and asking, “What’s on your mind?” It’s picking up that obscure trail mix they like because you remembered how they ate it all last time. The little things matter a lot more than your inner rom-com protagonist may want to admit.

Because honestly, anyone can book a hot air balloon ride once. But consistently showing up? That’s where love lives.

5. Self-Awareness Is a Superpower

Confession time: I’ve not always been the best communicator. Some years ago, during a stretched-out breakup-that-wasn’t-official-yet, I realized I’d been quietly seething about things I’d never once brought up in conversation. How was I expecting my partner to fix something they didn’t even know about? (Plot twist: they couldn’t.)

The key to resolving conflicts—and growing through them—is to first figure out your own emotions. What’s actually bothering you? What’s the underlying need or fear? Then (and this is the hard part), communicate it in words, not passive-aggressive sighs.

It’s like putting together a map before you try to lead someone to a solution. When both partners are self-aware, they can navigate even tricky terrain with grace instead of stumbling around like a bad improv duo.

6. You’re Allowed to Outgrow People

Picture this: you have a favorite pair of hiking boots. They’ve climbed peaks, crossed streams—you’ve got history. But eventually, they wear out. They don’t quite fit right. And as much as you resist, you know it’s time to let them go.

Some relationships are like those boots. And no, that’s not an insult to anyone I’ve dated—it’s just an acknowledgment that not all connections are built to last forever. Sometimes, people help us grow in a particular season, and then it’s time to move on. It doesn’t have to be anyone’s fault. Growth is bittersweet that way.

Don’t cling just because letting go feels like failure. It’s not. It’s a natural part of becoming the person you’re meant to be.

7. Love Starts with You

I know, I know. It’s a cliché worthy of a needlepoint pillow. But hear me out: Without a firm relationship with yourself, every other relationship is going to feel shaky. If you’re insecure, you might over-apologize or overanalyze. If you’re avoidant, you might keep people at arm’s length. Self-love is the foundation, not a bonus.

For me, this lesson really landed during a solo camping trip a few years back. There I was, alone under a sky full of stars, realizing how peaceful it felt to just be. That kind of self-acceptance didn’t come overnight, but it taught me that I don’t need someone else to “complete me”—I just want a partner to walk alongside me. Someone whose company makes the journey even better.

8. Laughter Fixes a Lot

If I’m ever on the fence about a relationship, here’s one litmus test I’ve come to trust: Do we laugh together? Not polite chuckles, but full-belly, tears-streaming, inside-joke kind of laughter. If the answer’s no, I’m out.

Life is heavy enough—taxes, flat tires, the one time I accidentally said “I love you” too soon. Relationships shouldn’t add to that weight. Laughter, even in the ridiculousness of miscommunication or mistakes, can lighten the load.

See, laughter is like trail mix: sometimes sweet, sometimes salty, and always good to have with you.

Take It One Step at a Time

If there’s one bigger truth tucked between these lessons, it’s this: Relationships aren’t about perfection. They’re about learning, adapting, and trying again. None of us get everything right. Heck, some of my “learning moments” have been embarrassing enough to require a stiff drink after.

But that’s the beauty of it. Love, like life, evolves in stages. Mistakes turn into stories. Endings make room for new beginnings. And no matter how daunting the path ahead, every step is worth it.

So take your time, laugh at your missteps, and trust the process. You’re doing better than you think.