“Does your grandaddy have a girlfriend?”

This was the question that stopped me—seven years old, missing a tooth, and halfway through a bowl of Frosted Flakes—mid-chew. My cousin Mya tossed it out there at our family reunion like it was no big deal, even though, for me, it was the equivalent of dropping a match on gasoline. My grandpa? A girlfriend? Wasn’t he supposed to be, I don’t know, just straight-up retired? Turns out, family stories are rarely as straightforward as we think—and if yours are anything like mine, they're full of plot twists, unforgettable characters, and just the right amount of chaos.

Let me back up.

So, my grandpa, Ernest Holloway Sr.—or Big Ern, as we called him—was the centerpiece of most family gatherings. He had this voice, deep and smooth, like the bassline of a Smokey Robinson record, and a swagger that leaned somewhere between "cool uncle" and "unbothered king." Born in Mississippi and raised on jazz and moonshine, Big Ern immigrated (okay, packed his bags and got on a Greyhound) to Chicago during the Great Migration. He was the type of man who could fix a car, knit a scarf, and roast a whole chicken—and I'm talking perfectly golden-brown—without breaking a sweat. But what made Big Ern legendary? His flair for storytelling.

The Best Storytellers Know When to Embellish

Take this one: “When I first got to Chicago, I walked into a pool hall and made $45 hustling some fellas who didn’t know I could play.” Depending on the audience (and his mood), that story’s number fluctuated: $45, $75, $150… until, at one reunion, someone shouted, “Ern, how you gonna say $500 when they weren’t even playing for money?” Big Ern just shrugged and gave one of his classic lines: “Never let the truth get in the way of a good story, son.”

This, as you may have guessed, shaped my entire worldview. From Big Ern, I learned that creating compelling narratives is as much about seasoning as a good pot of gumbo. Stories—like relationships (you see what I did there?)—aren’t just about facts. They’re about texture, flavor, rhythm. It’s about feeling what needs a dash more paprika and knowing when to let something simmer.

Every Family Has Their “Meal Ticket”

Big Ern wasn’t just a storyteller. He was also the catalyst for one of the most infamous traditions in the Holloway household: the Family Spades Championship. Now, if you don’t know spades, let me tell you—it’s not just a card game; it’s a blood sport. Think of it like basketball, but for people who can calculate the number of tricks left in a game while also holding a full plate of baked mac and cheese.

Every Sunday after church, my parents and uncles would drag me and my cousin Mya to my grandparents’ double-decker until we were old enough to “catch hands” and play. Here’s the thing: You don’t gain confidence in Holloway spades. You survive. My mom once accused my dad of reneging, and Big Ern stepped in the middle, not to calm the argument, but to replay the eight of clubs like a game-changing highlight on SportsCenter.

This wasn’t just a weekly reckoning—Spades became our family’s symbol for understanding relationships. I mean, it’s all in there: trust, communication, strategy, and a deep belief some things are worth defending to the grave. Big Ern once told me, “Boy, life is spades—you gotta know what to bid and when to bluff.” (This, to be real, also applies to dating. More on that later.)

Unlikely Matchmakers…and Hard Lessons

Which brings me back to the "Does-your-grandaddy-have-a-girlfriend question." Turns out, Big Ern had a “friend” from choir rehearsal. Her name was Miss Laverne, and she brought banana pudding to all the church picnics like it was currency. People whispered. My grandma had passed a few years earlier, and the sight of Big Ern and Miss Laverne walking into First Baptist together sent shockwaves through the aunties.

“They’re adults, let them live!” my cousin yelled during one heated discussion, while my aunt Diane insisted, “A man needs to grieve for at least ten years—minimum.” Meanwhile, my dad? He nodded toward me, as if to say, “Watch and learn.”

And learn I did. Because for all the whispering, there was something deeply kind about how their friendship evolved—not forced, but easy. That’s where I think most of us go wrong in relationships. We’re so caught up in the idea of something lasting or fitting a script (or what Aunt Diane thinks is right), we forget the importance of just showing up, being kind, and seeing where things lead. Call me sentimental, but Miss Laverne taught me that putting in the effort—banana pudding or otherwise—is one of life’s simplest but most profound gestures.

Love Is Seasonal But Storytelling Is Forever

Now, you might think the lesson here is that you can find love at any age, even when your hair’s gone gray or you get winded climbing stairs. And sure, that’s true. But for me, the deeper takeaway from stories like Big Ern’s is this: Love and connection—whether romantic or familial—work best when stitched together by moments that live on long after they’ve happened.

Because here’s the thing about Big Ern: He didn’t need everyone to fully believe his $500 pool hustle. And Miss Laverne didn’t need him to propose or make public declarations of love. What mattered were the moments we kept returning to, the ones we built on every Thanksgiving, every fish fry, every Sunday on the porch.

So, How About Your Story?

Maybe your family’s Big Ern is your grandma, who still crushes Zumba classes, or your cousin who can’t cook but swears by their air fryer. Or maybe it’s you, trying every day to build relationships out of shared laughter, memory, and a little exaggeration here and there (it’s okay; Ernest Holloway Sr. would approve).

What matters is that you take those stories—messy, hilarious, bittersweet—and carry them. Because, just like a good spades game, life’s won not by playing fast or perfect but by staying in play and making the moment count. And who knows? Maybe one day you’ll tell your kids about how their great-grandpa, Big Ern, found love in choir rehearsal and left us all debating whether that pot of banana pudding was really worth the hype.

Spoiler: It was.