Cloak and Dagger at Lolinda ($10)
A "tequila Manhattan," the Cloak and Dagger brings together Calle 23 reposado tequila, Cynar, Rothman & Winter's Orchard Apricot, and Angostura bitters. The Cynar flavor particularly shines against the herbal tang of tequila, with a hint of citrus aroma thanks to the orange peel garnish.
Berlinetta at Burritt Room ($12)
Be still, my whiskey-loving heart—I think I'll ask the Berlinetta to be my Valentine this year. It starts with a blend of dueling whiskies, Old Overholt rye and Four Roses Yellow Label bourbon, bittered-up with Cynar, Carpano Antica, and Fee Brothers orange bitters. The effect is similar to a good Old Fashioned, with a little punch of bitter something-extra from the Cynar.
Protect Ya Neck at Nopa ($10)
Nopa's been showcasing mezcal cocktails on their menu since last fall (all of which are named for Wu-Tang Clan songs. Now that's effing romance!), and the Protect Ya Neck is as aggressively good as the name would suggest. Del Maguey Mezcal Vida is blended with Cynar, Gran Classico, and lime juice. The drink is intensely tart, then mellows to a smokey rich bitterness, entirely selling me on the brilliance of a mezcal-Cynar combination.
Grandma's Sweater at Trick Dog ($10)
What stands out in this juicy-tasting cocktail from Trick Dog is the bitterness of Zucca Amaro, which is flavored with rhubarb, cardamom, and bitter orange peel. It's deliciously matched with gin and bitter lemon soda, plus a long slug of housemade blood orange syrup.
Church at Locanda ($10)
The Italians understand the bitter cocktail better than many of us, what with their Negroni and Campari and such. The Church at Locanda delves into the citrus side of this more heavily, but stays true to tradition with its blend of Beefeater gin, Cocchi Americano, Aperol, and lemon. The Aperol dominates the flavor profile, making the overall experience a bittersweet one.
Palomaesque ($9), Comal
Over in the East Bay this Valentine's Day? Never fear! The Palomaesque at Comal in Berkeley will have you feel bitter (in a good way) in no time (even if it is pink). A variation on a Paloma, Don Amado Rustico Mezcal is mixed with Cocchi Americano, grapefruit, lime, honey, salt, and soda. You'll get some nice quinine bitterness from the Cocchi Americano, and a note of bitter citrus from the grapefruit.