Everyone who’s ever eaten an oyster remembers his or her first time. The peer pressure. The slippery substrate coated in blood-red cocktail sauce. The texture of something cold and tongue-like sliding along the roof of the mouth and, ideally, immediately down the esophagus before the brain could trip the gag reflex—or, if one was brave enough to chew it the first time around, the tiny tidal wave of foreign flavors, bursting forth with notes of butter and brine and bits of primordial organs.

Unfortunately for many people, this first experience is also their last. It’s just too creepy and weird. But for the select—and they do consider themselves select—few people who push on through that initial traumatic swallow and onto the next bivalvic adventure, oyster eating can become an unparalleled culinary pleasure.

Our managing editor, Jessie Rogers, is one of the unlucky few who was forced to down an oyster against her will (at the urging of this author) and barely lived to tell the tale. (The slew of cocktails at Rialto that followed didn’t help either.) The guilt’s been eating away at us ever since, so we called in Shore Gregory, director of business development at Island Creek Oysters and Boston’s own Oyster Whisperer, to show her how to face down even the gnarliest plate of Belons without fear. These are his tips.

1)    Belly up to the bar at a quality establishment that takes their oyster program seriously. Not all raw bars are created equal, so if you’re looking to jump back on the horse, pick a thoroughbred, so to speak. We’re big fans of Rialto’s and Sel de la Terre’s Monday night dollar oyster nights, while Gregory’s favorites include Neptune Oyster, B&G Oysters and Eastern Standard, where we met up with Gregory for our shellfish seminar. “Garrett’s got a great program here,” Gregory said approvingly of Eastern Standard owner, Garrett Harker, as our waitress listed off this season’s sought-after options. “And Jeremy [Sewall] is such a great seafood chef.”

We put together a sampler of Wellfleet oysters from the warm waters just off the Cape; Beachpoint oysters, grown by a small boutique producer near West Barnstable, Mass.; and Island Creeks, harvested year-round from the icy flats of Duxbury Bay.

2) Try a variety of oysters before you decide what you like. Even though most of the oysters grown on the East Coast are the same species (crassostreus Virginica), they taste different depending on the temperature and salinity of the water in which they’re grown—much like a California Chardonnay will taste dramatically different from a French Chardonnay even though they’re made from the same grape. (Side note: It’s for this reason that longtime wine drinkers will roll their eyes when you say you “hate Chardonnay” when in all likelihood, you only hate the cheap, sour domestic Chardonnays you’ve been served in the past.)

One thing Gregory’s observed over time is that warm water oysters, such as those grown in Wellfleet or along the Pacific Coast, tend to have a more mild, mellow flavor—a chicken soup kind of flavor, on this particular night—due to the lower nutrient content in the water, which makes them easier for oyster amateurs to handle. Kumamotos, from Nagasaki, Japan, are known as the quintessential beginner’s bivalve, and ostreaphile extraordinare Rowan Jacobsen loves them because they are “sweet as heck and they smell like honeydew.”

Meanwhile, Island Creeks are some of the saltiest, briniest buggers you can find ‘round these parts—and for the oyster eater who loves the idea of eating a little slice of the sea (or for people who prefer salty tastes to sweet), ICO’s will hit the spot.

And that’s not even scratching the surface of what’s available, from France’s coveted Belons (also known as European Flats) and their cousins, the Chiloes, to the buttery Sydney Rocks of New South Wales, to the tiny smoky Olympias of Washington’s Puget Sound. Just as no one can say they’ve truly explored the wine world if all they’ve had is Franzia, you can’t really rule out oysters entirely until you’ve sampled a wide range of what’s out there.

3) Go with someone with experience. A high quality restaurant will know how to shuck ‘em as well as source ‘em. While it seems simple enough—just pry the guys open and set them on a bed of ice—it’s easy to mess up, either by cracking the shell, failing to properly separate the oyster from the adductor muscle that attaches it to the shell, spilling out the “liquor” (seawater), or slicing into the middle of the meat. Gregory compares this to overcooking a steak: it’s a lamentable waste of a good thing. A perfect oyster will fill most of the shell, be presented with plenty of seawater still inside, and come away cleanly, giving the customer the most meat for their money.

4) Go naked. Maybe you’re used to having globs of condiments on hand to make the medicine go down, but Gregory suggests you lay off the (cocktail) sauce. When you’re sitting down to a dozen oysters that are literally fresh off the boat, drowning them in dollops of the stuff is a bit sacrilegious and pointless, like putting ketchup on your caviar. Try yours with just a squeeze of lemon, or maybe a light dash of mignonette if you’re really in need of a kick—after all, it’s an oyster, not a damn hot dog. And don’t forget to chew.

5) Don’t force it. Like anything in life, oyster appreciation comes with time. Few people love goat cheese, or hoppy beer, or tannic red wine the first time they try it—it tastes like something gone wrong, out of sync with our natural, human attraction towards sweet, simple flavors. But for those with the patience and the stones to stick with it, the rewards are great. Oysters are good for our bodies (they’re high in zinc, a factor which some researchers think gives it its fabled aphrodisiac qualities), and they’re good for the environment. They filter and clean the water wherever they are, they’re often harvested by hand instead of by dredge (which damages the ocean floor), and they’re at the bottom of the food chain, so removing them from an ecosystem does less damage than harvesting other kinds of sea creatures (like swordfish and salmon, both predator fish).

What’s more—local oysters from Massachusetts are held to incredibly high standards of quality, required to be of a certain size before they’re harvested, and, of course, are much fresher here than they would be in Austin, Texas or Denver, Colorado. So here, you can feel good about every aspect of oyster eating—which you can’t always say about a steak, cooked properly or no. Plus, eating them will earn you points with the next sophisticated lady or gent you take out to the bar. (One couple we know even got engaged after a night out on the town gulping down oysters. We’re just sayin’.)

But what of Jessie? Did we convince her to embrace ostreophilia with the rest of us?  “I almost enjoyed the milder oyster,” she said after slurping down one each of the diverse sampling we chose for our table, “And the wine. The wine helped.” (We went with the Poggio Della Costa, for the record.)

–Ryan Weaver

The Shore Gregory TeaParty 10

Many thanks to Shore Gregory, who will never forget the time he tried Thomas Keller’s famed Oysters with Pearls at Per Se (made with his own Island Creek Oysters), and to Rowan Jacobsen, author of A Geography of Oysters, for providing our favorite funny, readable and poetic guide to oyster eating in North America, from the Pacific Ocean to Prince Edward Island. You can read more of his writing here.