a person holding a couple of boys
Kathleen Sebastian
The author, his father, and his older brother in the early 1980s.

By late afternoon at Churchill Downs, I’d lost track of the number of bourbon drinks I had consumed. There were icy mint juleps by the bucketload and more than a few Old Foresters on the rocks. I was feeling pretty damn good.

My wife, Sally, and I had left the kids with Grandma and Grandpa and traveled to Louisville for the 150th running of the Kentucky Derby. This was Oaks Day, the Friday before the Derby, during which the guests wear pink for the main event: the running of the three-year-old fillies (in other words, young-girl horses). It was our first time at the Derby, only my third time at a horse track, and none of our bets had paid off yet. As guests of Longines, the official timekeeper of the Derby, we got to join the CEO and watch the Oaks from a grassy area right next to the track. That required crossing the dirt raceway. It had been raining on and off all day, so the track was sopping-wet mud. My wife took off her high heels and walked barefoot. I decided to brave it in my loafers, which became caked in mud and horse shit. I’m not sure a cobbler can ever restore them, and I’m not sure I care. That’s historic mud and shit right there! And the thrill of feeling the fillies pound right past us and hearing the hundred thousand spectators roar more than made up for one ruined pair of shoes. It’s now a core memory.

I never take these types of experiences for granted. But they often mean leaving my two daughters for stretches of time. I haven’t celebrated a Father’s Day at home in five years, because Men’s Fashion Week in Milan always falls in the middle of June. So I always spend part of that day reading Esquire.com, which has a trove of stories about fatherhood. My favorite is an essay by Tom Bissell about raising daughters. “To raise a son is to teach him how to master his world while knowing he’ll get hurt,” Bissell writes. “Raising a daughter can and should be about that, too, with the added trick of making her aware that the world will seek to hurt her in far subtler ways. The little boy’s mastery will be applauded, but the little girl’s mastery will often be resisted.” I think about this line at least once a day while parenting my two girls.

As an eight-year-old, I must have caught a nice buzz.

This month, Esquire published a fun, irreverent package of stories about how to be a dad—not a father. The comedian Jim Gaffigan offers advice on how to tell a dad joke; we question whether it’s okay to have a favorite child (answer: yes), endorse the practice of showing your kids R-rated movies, and offer a quiz that will determine whether you’re a dad or a father. My contribution is a short piece about the unexpected joy of becoming my father. Whether he knows it or not, my dad has given me a map for life—as both a father and a man. But he’s not the only father figure in my life. My older brother has filled that role. So have uncles, teachers, coaches, bosses, and my late father-in-law, John. My mom, too. You don’t have to have a Y chromosome, or be a father, to help bring up a man.

On our last night in Louisville, I was reminded of another father figure in my life. Late in the evening after the Derby, Sally and I decided to have a nightcap at the hotel bar. I wanted one last taste of Kentucky bourbon, and my eyes landed on a Manhattan, which I hadn’t had in years. Soon I got down to the bottom of my drink, where the cherry awaited. I popped it in my mouth, and the bourbon-soaked sweetness unleashed a powerful memory. My grandfather, my dad’s dad, drank Manhattans at home. And when I was a boy, he’d let me eat the cherries from the bottom of his glass. As an eight-year-old, I must have caught a nice buzz. He’s been dead nearly twenty-five years, but the taste of that cherry in a Louisville hotel bar brought me right back to his kitchen.

Need some dad advice? Check out Esquire’s new fatherhood column, Ask Dr. Harvey Karp.