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Frankly, My Dear, I Do Give a Damn…

Can an avowed Manhattanite become a Southern Gentleman in a matter of days?

Unless I change my name from Joshua David Stein to something like Sterling, Blaine or Hunter—or maybe all three at once—there are limits to how close I can come to resembling a true Southern Gentleman. I’m not talking about Rhett Butler, but the modern version: Today’s Southern Gentleman is a rarefied breed, half candy cane and half etiquette ninja. His skill set is a mysterious assemblage of charming diversions and arcane convention. He speaks slowly but acts decisively. He says “ma’am” and “sir.”

As a neurotic New Yorker, the extent of my politesse consists of trying, often unsuccessfully, to determine whether or not it would be insulting to offer my seat to a woman who may or may not be pregnant on the subway. I talk the talk much more than I walk the walk. I dither. And when I call someone sir or ma’am, they usually recoil, saying, “Sorry, I don’t have any change.”

But the charm of the southern bourgeoisie had always intrigued me. They seemed like valiant porters from an earlier time, who skated by on privilege and quiet confidence, open vowels and extraneous syllables. It wasn’t just the accent, it was the action. The body of knowledge held by a Southern Gentleman was, to me, dark matter. So I made my way to Sea Island, Georgia, both a proving ground and training center for newly minted—and thoroughly mint-juleped—southern gents.

Sea Island is a sprawling, 1,235-acre resort that opened in 1928 and currently occupies the entirety of a small coastal island in south Georgia. The island, which sits 80 miles north of Jacksonville, Florida, is an elegant spread of private houses and guest villas, connected by lanes shaded by live oaks dripping Spanish moss. Most activity centers around the Cloister at Sea Island, an elegant, vaguely Spanish inn with 175 rooms, long Versailles-like hallways and a patio that looks out over the Black Banks River. On a recent evening, a sloop was moored on the pier. Its name, written across the bow, was Schmuck. Maybe I would fit in after all.

The first lesson I picked up in my crash course was that the Southern Gentleman must pack for his vacation an inordinate amount of cleanly pressed khaki pants and a gentle rainbow of pastel polo shirts. Skinny jeans are definitely not in vogue. Interestingly, the piqué cotton polo shirts I saw sported at afternoon tea or, later, in the cigar-smoking room—cigars being another thing a Southern Gentleman enjoys—were also the preferred workout gear in the fitness club. At Sea Island, they take the term undershirt literally.

My next tutorials came fast and furious, thanks to the island’s status as a grown-up playground. There are 36 holes of championship golf at the Lodge at Sea Island, which overlooks the St. Simons Sound, as well as three squash courts, a shooting club and sailboats back at the Cloister.

Over the next few days, I shot, squashed, swung and tacked with abandon. But much of the advice doled out by impeccably polite men in light-colored slacks was the same. Jared Zak, my golf instructor, eyed me neutrally as I tried to drive a ball like it was a Mack truck. “Try to relax,” he said. “You don’t need to swing that hard.” As I clutched a Beretta semi-automatic shotgun, missing clay pigeon after clay pigeon, as they lofted away before falling into the marsh, Jake Duncan, my teacher, amiably mentioned it might be a good idea to relax just a bit, at least while I was holding the gun.

But the best piece of advice that came my way was courtesy of a man in spotless white shorts. Steve Hall, an on-property squash pro, had just finished clobbering me on the courts—an episode that left me soaked in sweat and Hall not even short of breath.

“Joshua,” Hall said as I panted, red-faced and spent, “it’s not about force. It’s about finesse.”

On the final night of my trip, sunburnt from my time on the golf course and exhausted from everything else, I donned khaki pants and a lime-green polo shirt I’d picked up in the gift shop and headed to dinner. At the threshold of the restaurant, I swung the door open, gently, and held it for an approaching southern lady. I waited, amiable. And as she approached, I smiled. “Good evening,” I said.

“Thank you, sir,” she said. And I, drawling out the vowels, replied, “My pleasure, ma’am.” I was well on my way.