Since you are in-the-know, and conventionally handsome, and are often asked to be a fit model in Canadian K-Swiss commercials, you likely already hit up Backbar, Somerville's Doug Flutie-sized cocktailery. But what you likely don't know is that they've got a new Fall drink menu so sexy, it could likely star in one of these damn K-Swiss commercials too. The highlights:
The Detour: They call it the Detour because it's what would happen if you first went to England for their Plymouth Gin, then went to Mexico for some Del Maguey Crema Mezcal, but on the way "you took a quick detour in New England for some apples (or in this case housemade apple shrub)".
West Barbara: Hmmm. Sooo... Barbara West was the second-to-last remaining survivor of the Titanic sinking (you win this one, Milivina Dean!). Perhaps she was into drinks made with sherry, lemon, mezcal & sugar? Though one doubts she'd want it with... wait for it... ice (NOTE: there is also a small chance this drink has nothing to do with Barbara West).
Rhuby Mela: This has apple brandy, maple liqueur, and something called Zucca in it. A quick primer on Zucca -- it's an Italian apertif whose name translates to pumpkin or squash, although its base ingredient is rhubarb, which gets combined with zest and cardamom and other curative herbs to make the booze. Also, beautiful people in Milan who wear fancy driving loafers are known for drinking it by the barrel, though given your own previously mentioned aesthetics, you likely already knew that.