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Had a Bad Day? It Turns Out, Chocolate Pairs Very Well with Booze

Perhaps by now you’ve had that enormous chocolate cake at Moody Tongue Brewing. We found three other can’t-miss combos.

Chocolate chip cookies are a great way to bring out the different flavors of whiskeys.   Photo: The Lunatic, The Lover & The Poet

Beer and cake seem an unlikely pair, but that doubt quickly dissipates once you’ve had a sip of a Moody Tongue brew and a forkful of the Pilsen brewery’s 12-layer, German chocolate stunner.

It got us wondering: Where else can we find unexpected chocolate and booze pairings that work remarkably well?

1. Chocolate chip cookies and whiskey

The Lunatic, The Lover & The Poet (736 W. Randolph St.)

“I’ve been drinking bourbon most of my adult life and I have loved chocolate chip cookies longer than that, and I never had them together,” says Tom Powers, managing partner of the West Loop wine bar.

This shortcoming dawned on him one quiet night at home early this summer while sipping his favorite beverage in close proximity to the cookie jar. He then did what was long overdue.

“There’s a natural marriage in the brown sugar and chocolate in the cookie and the whiskey in the bourbon, and as you explore different whiskeys, it brings out their different flavors,” Powers says.

But what good was this knowledge without sharing it? In July, Powers organized a whiskey-and-cookie tasting, offering three 1-ounce pours of whiskey and two cookies for $35. He did it again last week. As of this week, it’s every Thursday. 

The whiskey choices will rotate. The cookie will not. Soft in the center, crispy on the edges, gooey with semisweet chips (though Powers says he might swap them for dark chocolate at some point), it’s an iteration of the one Mindy Segal perfected at his request when both worked at Marche, Powers as general manager, Segal as pastry chef.

The cookie “works remarkably well with a wide array of whiskey,” says Powers, especially Japanese varieties with their crisp, clear notes. But the standout whiskey so far has been Widow Jane out of Brooklyn. “It has the right kind of sweetness. There is unequivocally a uniquely chocolate element to it,” he says.

2. Salted dark chocolate caramels and a gimlet

North Shore Distillery (13990 Rockland Rd., Green Oaks)

The north suburban distillery’s food menu is limited by design, but co-owner Sonja Kassebaum always includes at least one sweet, usually something chocolate. “It has a nice pairing capability with a range of spirits and cocktails,” she says.

Case in point: salted dark chocolate caramels currently on offer at the tasting room ($2 for 1, $5 for 3). While these aren’t from her favorite source, Katherine Anne Confections, they work just as gorgeously with her suggested drink, the Ginger Gimlet ($10), made with Distiller’s Gin No. 6, fresh lime juice, and ginger simple syrup.

“The ginger plays nicely off the caramel notes, but the acidity from the lime helps cleanse the palate so that neither overwhelms the other,” she says. “Each bite of caramel is a new bite. That’s what I try to do with pairing anything, but especially dessert.”

Kassebaum is saving her other knockout pairing for later this fall, when it tends to sell better: chocolate-covered potato chips and a classic Old Fashioned. “The alcohol is a good balancer, and with the citrus and bitter notes, it helps cleanse the palate so you can go back in for more salty and fatty and go around the circle again,” she says.

 3. Chocolate ganache and vermouth

Rootstock Wine Bar (954 N. California Ave.)

A single, silky quenelle of chocolate ganache ($2) is the only dessert at this Humboldt Park wine bar. It’s topped with a seasonal fruit preserve—blueberry right now—drizzled with olive oil and dotted with sea salt, it goes well with port, madeira, and cognac, all of which owner Tonya Pyatt will gladly suggest. But recently, beverage manager Jamie McLennan turned her onto a pour he says trumps them all: a made-in-Brooklyn vermouth.

Whatever botanicals Uncouth Vermouth founder Bianca Miraglia doesn’t forage to make her wine, she grows on her upstate New York farm. “She also doesn’t believe in adding sweetness, which is very uncommon in vermouth production,” McLennan says.

Rootstock carries three Uncouth vermouths: apple mint, hops, and—the one you want—wild raspberry ($12 for a 2-ounce pour). How it plays out with the ganache is “fascinating,” McLennan says. “Both are bitter, tangy, and a touch salty, which helps them play nicely off one another, and the moderate sweetness of the chocolate really intensifies the flavor of the wild raspberries, which is what I find truly delicious.”

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