Cats, Cranberries, And Questionable Maps: A Very Tipsy Holiday Special

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Holiday spirit tastes better when it comes with stories, experiments, and a little chaos. We kick off with a surprise: a red blend built from an AI “recipe.” The winemaker hated the idea, followed the constraints anyway, and ended up impressed by the result. That tale sets up a larger theme as we juggle innovation and tradition—how to honor craft while giving new ideas a seat at the bar.

From there we throw open the door to real-life hosting. We swap Rochester misadventures, bottle share finds, and Irish pub nostalgia while laying out a blueprint for stress-light entertaining: focus on meats, let guests bring sides and desserts, set early, and actually use the nice china. We talk seating 35 without losing your mind, why punch bowls deserve a comeback, and the etiquette of shipping gifts that shouldn’t be opened before the big morning.

Behind the bar, we get hands-on. A cranberry bourbon sour becomes a lesson in restraint—choose one tart driver and give cranberry room to paint the glass. A rum old fashioned with agave and orange bitters proves that sweetness should support, not smother. We debate maple syrup in an old fashioned, weigh a New York sour’s wine float, and rethink orphan liquor into party-ready punches with ginger and pineapple. Then we go deep on nog and milk punch: how to whisk yolks with sugar, fold in whites for lift, and grate nutmeg; why clarified milk punch looks like amber and drinks like silk; and how a few historic techniques can make your holiday table sing.

By the end, you’ll have a shortlist of crowd-pleasing winter cocktails, a smarter approach to hosting big family gatherings, and a fresh take on what tradition can mean when you let flavor lead. If this episode made you thirsty, share it with a friend who’s on drink duty, hit follow for more spirited conversations, and drop your favorite holiday cocktail in a review—we might mix it next time.

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Jamie Flanagan @DJJamieDetroit

Matt Fox @fox_beazlefox

August Gitschlag @rawgusto

Merch www.WearingFunny.com