When I was a child, my family had a tradition that occurred every summer evening in Santiago: someone would announce, “La sobremesa empieza” – and that was our signal. Plates were cleared, wine glasses refilled, and the real magic began. Sobremesa, for the uninitiated, is the period after a meal when conversation flows like a second course. But in my family, sobremesa wasn’t just conversation; it was an art form, part improv comedy, part oral history, and, occasionally, part courtroom drama.

My parents, both teachers, would orchestrate the evening, gathering us around the table as if they were conducting a seminar on life. My abuelita would chime in with grandiose tales of her youth, her theatrical gestures rivaling anything you’d find on a Netflix drama. My tías and tíos would contribute their running themes of ridiculous characters, rivalries, and romance, debating whose story was closest to “la verdad,” the truth. And somehow, amidst all of this, a younger version of me was taking notes – not because I knew I’d be writing about it someday, but because the stories shaped how I thought about love, connection, and relationships.

Here’s the thing about family lore: it’s not static. Every re-telling becomes a remix. Stories evolve based on who’s at the table, who’s interpreting the characters, and who’s conveniently omitting certain incriminating details. But through the decades of listening (and the years I later spent deconstructing my family’s tales while awkwardly learning to date as an adult), I realized these stories offered far more guidance than just entertainment. They shaped the way I understood relationships—what bonds us together and, just as importantly, what can pull us apart.

The Tale of “Tío Romántico” and the Never-Ending Serenades

In my family, there’s a legend about my uncle—let’s call him Tío Romántico. As the story goes, when he was young and madly in love, he once serenaded his high school crush every night for two weeks beneath her window. He would sing boleros—lush, melodramatic love songs—with his entire heart, rain or shine. My abuelita swears he sourced lyrics directly from Pablo Neruda’s poems, scribbled dramatically onto the back of napkins.

Here’s the tragic plot twist: the girl he serenaded did not know her mother had been intercepting her letters and misdirecting her suitors. Por supuesto, she thought she’d been ghosted. Tío Romántico, convinced he’d been rejected, stopped singing and disappeared into a moody three-month solo road trip across the Chilean countryside.

The moral got debated every single time this story popped up (which was often). Was it romantic to risk vulnerability in this way, or blindly foolish? Some family members argued it was proof of love’s capacity for perseverance. Others insisted the serenades were a lesson in mutual communication—singing in the rain only works if the person you love can actually hear you.

Over the years, I’ve taken this story to heart. Today, I tell friends navigating their own dating lives this: if you’re feverishly writing paragraphs in your love language, make sure your person speaks it. For all the effort Tío Romántico poured into his grand gestures, one honest conversation about mutual expectations might have saved him months of heartache. (And some very soggy shoes.)

Sobremesa Wisdom: “El Amor Es Para Valientes”

Every family gathering inevitably came back to this adage: love is for the brave. (It sounds better in Spanish; trust me.) My tías had dozens of anecdotes to illustrate the point. There was the cousin who quit his corporate job to follow his partner to a one-bedroom apartment in Buenos Aires (spoiler: they’re still together). And the great-uncle whose courtship included handwritten sonnets he would mail every week to his future wife.

But “bravery” wasn’t only about dramatic gestures. My father, usually the quiet sage at our table, would argue that courage was just as necessary in the quiet moments. He’d tell us about how he and my mother, also teachers, spent years organizing protests for better pay at the local school. During the hardest times, when the school administration wanted them gone and the students were restless, it wasn’t grand declarations of loyalty that kept them together. It was grit. It was being able to sit at dinner, share a glass of wine, and agree they were a team despite everything trying to pull them apart.

What I’ve learned from their experiences is this: relationships aren’t solely about the fireworks. Courage isn’t always loud. Sometimes real bravery is in the honesty required to say, “I’m scared. Let’s figure this out together.” Families don’t always get it right—in fact, they stumble often—but mine taught me that vulnerability is the cornerstone of connection, even if it feels messy or uncomfortable.

The Case of “Cousin Susana” and the Curious Cake

No family story would be complete without a little humor—or dessert. Enter Cousin Susana, the family’s self-proclaimed gossip columnist, whose anecdotes always came with unexpected lessons. One year, during a particularly heated sobremesa session, Susana told the table about her notorious “Curious Cake Breakup.”

Back in university, she’d been dating this charming musician whose charisma seemed endless. When they hit their six-month anniversary, she decided to bake him a cake from scratch as a surprise. (Her grandmother’s recipe—lest we forget, this family reveres both boleros and pastries.) What she didn’t anticipate, though, was catching him red-handed texting his ex while the cake was still cooling on the counter.

Her response? She calmly sliced the cake, handed him a generous piece, and said, “Enjoy it while it lasts.” Then she ate the rest herself. And by “rest,” I mean all seven remaining slices.

I think about Susana every time I hear someone blame themselves excessively post-breakup. She taught me—and later, herself—that relationships don’t demand absolute perfection. Sure, they require effort. But if someone texts their ex while you’re investing in homemade pastry? That’s not on you, mi amiga. That’s their loss.

Susana framed the experience as bittersweet but transformative in the end. “Every slice taught me something,” she joked. (By that point, the wine usually started flowing, and her delivery was halfway Shakespearean.) She’d go on to meet her now-husband years later, but she claims that breakup cake was the best thing she ever baked.

At the Table of Our Lives

The stories in my family taught me that relationships—whether they’re between friends, romantic partners, or relatives—are built on tiny moments we piece together, sobremesa-style. Everyone contributes something to the weave. The humor, the heartbreak, and the lessons all collide in beautiful, chaotic harmony.

What my family’s sobremesas really gave me, though, was a way to frame my own stories. A bad date? Hilarious fodder for someone else around the table. A romantic risk that backfired? Proof that, at least, I was giving love the bravery it requires. And the quiet moments, the ordinary tedium of connection, became the backbone of my belief in the magic of relationships.

So, when you find yourself at your own life’s metaphorical sobremesa—whether with family, chosen friends, or someone you love—remember this: stories have a way of bringing us closer, grounding us in something greater. They’re your guidebook for navigating everything from first dates to forever connections. And if you don’t like the ending just yet? Stay a little longer. Sometimes, like the sobremesa itself, the best parts happen when you think the meal is already over.