Every great Christmas date needs a muse, and this one arrived with brass, wit, and a wink: Ana Gasteyer’s “Sugar & Booze.” Her jazzy ode to holiday indulgence got us wondering why sugar and alcohol feel so synonymous with Christmas in the first place. A little digging revealed that the pairing is older than nearly every Christmas tradition we know. In medieval Europe, sugar was rare and costly—saved for feast days and religious holidays—while spiced wines and sweetmeats marked moments of celebration. By the 1600s and 1700s, colonial kitchens relied on rum and brandy to preserve fruitcakes that were meant to last the whole season, and nog-like milk punches warmed taverns across the colonies. Victorian cooks steeped their puddings (and their guests) in spirits, and eggnog—our chosen centerpiece of the day—became a festive winter staple long before Santa ever touched a glass. With centuries of history behind the pairing, we decided to devote our entire date to exploring every way Christmas has married sweetness and spirits.

The day opened with Eggnog Bourbon French Toast Muffins, warm and custardy with the unmistakable holiday trio of nutmeg, cream, and whiskey. Our neighbor Siera joined us for breakfast, chatting over Apple Cider Mimosas while we prepared gingerbread dough. The house smelled like brown sugar, spice, and December itself. On the counter, silicone molds waited for the day’s first big craft experiment: making edible shot glasses from chocolate, gingerbread cookie dough, and crushed peppermint.

Before the ovens heated up again, we whisked together Bailey’s Irish Cream mousse crowned with sugared cranberries and revived our old “gingerbread cadaver” cutters to create a new generation of Tipsy Gingerbread Men. And lunch was no exception to our theme, complete with brown sugar and bourbon glazed ham sliders.

By early afternoon, our close friends Corinne and Kris arrived, folding seamlessly into the cheerful kitchen chaos. Together we baked, shook cocktails, and taste-tested as we went—Mini Gingerbread Martinis, Rum Rum Rudolphs, gingerbread mocktails for the kids, and glasses dipped in cinnamon-sugar rims. Between batches, we played rounds of Sugar & Booze Trivia, learning about all the unique combinations of sweets and spirits that have been combined for festive fare. 

Dinner carried the theme without overwhelming it—a roast turkey breast with cranberry port sauce, roasted root vegetables, salad, and sparkling wine to bridge the final hours of daylight. As Ana Gasteyer’s album looped back to “Sugar & Booze,” the whole day felt like a playful tribute to both the song and the history behind it: the centuries when sweetness was a luxury, when spirits preserved both fruit and festivity, and when Christmas was one of the few times ordinary people tasted true indulgence.

After the kids went to bed, we leaned into the evening’s cozy absurdity: Ana Gasteyer’s classic “Schweddy Balls” sketch from SNL, followed by The Office’s “Benihana Christmas,” which features a fictional sake-nog joke that led perfectly into our annual international nog tasting. This year’s star was tamagozake—Japan’s warm blend of sake, egg, and sugar. Historically a cold-season remedy, it turned out to be an unexpected but delightful addition to our global nog repertoire, its simple ingredients echoing centuries of winter comfort.

By the end of the night, it was clear that the real joy of Sugar & Booze wasn’t just the cocktails or confections. It was the sense of continuity—tracing how these ingredients traveled through time, how preservation became tradition, how rare sweetness became celebration, and how people across centuries found warmth together in the coldest part of the year. With friends gathered around the table, flour dusting our shirts, holiday music swinging through the house, and spiked desserts passing hand to hand, it felt like we had stepped right into that history and whisked it into something entirely our own.

Activities

  • Ana Gasteyer “Sugar & Booze” Kickoff

  • Holiday Eggnog History Chat

  • Chocolate / Peppermint / Gingerbread Shot-Glass Crafting

  • Gingerbread Decorating

  • Sugar & Booze Trivia

  • Holiday Baking Marathon With Friends

  • SNL “Schweddy Balls” Viewing

  • The Office “Benihana Christmas” Episode

  • Christmas Music Lounge: Ana Gasteyer + Straight No Chaser

Menu

  • Eggnog Bourbon French Toast Muffin Cups

  • Apple Cider Mimosas

  • Bailey’s Irish Cream Mousse With Sugared Cranberries

  • Drunken Gingerbread Men

  • Bourbon Brown Sugar Ham Sliders

  • Mini Gingerbread Martinis

  • Gingerbread Mocktails

  • Rum Rum Rudolph (Cider, Cranberry, Ginger Beer)

  • Fruitcake

  • Rum Balls

  • Turkey Breast With Cranberry Port Sauce

  • Roasted Root Vegetables

  • Sparkling Wine Cranberry Sparkler

  • Tamagozake (Japanese Warm Eggnog)

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The Peppermint Twist