SIBLING RIVALRY

525 TREMONT ST., SOUTH END, BOSTON. 617.338.5338. SIBLINGRIVALRYBOSTON.COM

By CHRISTINE LIU | Photo By Derek Kouyoumjian

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I find Matthew Lishansky, director of operations at UpStairs on the Square, at the bar welcoming my rain-soaked ass with a hug and kiss. "I've never been here before, but my friend Jess used to be the pastry chef, and begged me to come," he says, dipping into a bowl of wasabi-coated peas. Little did I know the evening would soon be rife with confessions such as "I'm trying to be the Carlton Banks of the new millennium," "John Oates is a big-time douchebag" and "I don't know if in execution I would really enjoy vegans—they're admirable, but I like bacon a lot."

Drink 1: Blood Orange Sidecar ($11). At our behest, bartender Adam produces a bloody take on the classic with brandy, Cointreau and freshly squeezed juice. Down the hatch. "I would even put more brandy in it," Matt whispers conspiratorially into my ear. With another luxuriant sip, he continues, "I love sidecars—they make me feel fancy, like I should have a watch fob." He pauses to peel off his sweater. "I tend to get naked when I'm drinking ... I hope you don't get offended."

Drink 2: White Cosmo ($11). A respectable lady endures her bar companion while nursing a cocktail. "It's great," she relates, twirling her pearls. "It's not so sweet, so you can drink more." She's onto us. Cue glasses of Reyka Vodka, Cointreau, white cranberry juice and fresh lime juice, dramatically dribbled with Chambord at the bar. Matt, tripping Proustian from his white cranberry juice childhood, shares dirt on UpStairs diners: Christopher Walken is "as nice as he looks" and John Malkovich is "a toucher—he clarifies things by squeezing your arm." I'm irrevocably creeped out.

Drink 3: The Red Slipper ($11). "So, I'm ... a sauce queen," says Matt, unapologetically sticking his finger into the goodness pooling in our bowl of ravioli. "I'm a big hand eater—well, not literally." We wash it down with Absolut Ruby Red, fresh red grapefruit juice, simple syrup and a splash of Campari, lavishly banging our buck with a top-off of Champagne Perrier Jouët. A couple at the bar joins our posse, gossiping cattily about the recent red carpet showing. Our companions confirm: "The Oscars are like the Superbowl of the South End."

Drink 4: Diplomatico Reserva Exclusiva Rum ($11). Everything at this point is taking on a shiny veneer, but we can't resist the frosted green bottle stamped with the stony visage of a statesman. The smoky-sweet Venezuelan import, aged in white oak barrels, jolts us awake with a whiff of brain-meltingly high proof. Soon the four of us throw down an unofficial 4.5th drink, a shot ($7) of Grey Goose Pear and cranberry juice to prove Matt's highly scientific theory that together they equal Banana Runts. The smell? Definitely. The taste? Who cares!

Drink 5: Spiced Pear ($11). Matt's been craving this from three hours ago, and I can't resist those pleading eyes. A dried pear chip perilously rides the rim of Leblon cachaça, fresh ginger, pear nectar, lemon juice and a splash of simple syrup. I'm suddenly consumed by hiccups, and Adams lovingly shoves a lemon wedge laced with bitters in my face. I bite. I'm healed. "It's all about the breathing," Matt helpfully offers. He turns and continues, "I'm going to chew on this nub, if you don't mind," reaching with fingers outstretched toward an unsuspecting piece of blue cheese.