5 DRINK MINIMUM: UPSTAIRS ON THE SQUARE

Down a cobbled street, up cheetah print carpeted stairs and overlooking Winthrop Square is Upstairs on the Square, a place where you can escape the drudgery of reality and enter a cocktail and wine-fueled fairy tale. It’s like a dollhouse (that you can get drunk in) with a purple, pink, teal, and gold-trim color scheme, funky chandeliers, and tea-cup light fixtures.

It’s not just for the dainty though. The 21-page drink menu is presented in a three-ring binder and includes an extensive wine selection, but they also tout “the cheapest Miller High Lifes in Harvard Square,” at $2 a pop. See? Something for every mom.

DRINK 1 (BARTENDER’S CHOICE):
MAGNOLIA ($9)
If this is a fairy tale, then bartender Brendan is the knight in shining armor. He starts us off with a Magnolia (Angostura Bitters, Verjus, and Lavender Tincture) named after the general manager’s daughter. It matches the décor: dark purple-red topped with a frothy rose pink layer that clings to the side of the lovely Coupe glass. My drinking partner Lauren and I settle into our high-back pink chairs and shrug off stress.

DRINK 2 (BARTENDER’S MOM’S CHOICE):
MOLLY RINGWALD ($14)
An old favorite that’s no longer on the menu, Molly’s half-gin, half-fresh-squeezed grapefruit juice and housemade elderflower liqueur. Brendan’s mom is a beer and wine lady, but she likes fresh juice, and today’s grapefruits were exceptionally red, he says, as he pulls out a container of ruby red juice from under the counter. Perfect for moms who need to slip something strong into their morning juice.

DRINK 3 (DRINK THAT REMINDS YOU OF YOUR CHILDHOOD):
FREE-FALL ($8)
A free-fall seemed fitting as a metaphor for my childhood, but it also just sounded delicious: Rye Whiskey, Allspice Liqueur, Campari, and Falernum. The dinner crowd’s thinned out and only a couple and an older man join us at the bar. “Do you get a lot of moms in here?” I ask Brendan. “Oh Yea,” he replies. “For the tea service on Sundays. There’s all sorts of hats—it’s like the Kentucky Derby in here.”

DRINK 4 (YOUR MOM’S CHOICE):
SHOT OF FERNET ($7)
The absolute last thing my mom would ever order is a shot of Fernet—my family has inoffensive mid-range white wine in our blood. But frequently tells me to “take care of yourself,” and I’ll be damned if a shot of Fernet halfway through a five drink minimum isn’t the best way to do that. It comes in a dainty leaf-etched glass, because even the Fernet shots are classy here. It tastes fucking disgusting. My mom would hate it.

DRINK 5 (YOUR CHOICE):
PISCO-SOUR ($10)
Brendan serves us his favorite egg white drink and surprises us with their famous Charlotte au Chocolat cake ($8). It’s swoon-worthy—dark, moist chocolate slathered in vanilla whipped cream and topped with a candied violet flower—and plays right into our fairy tale delusions. I wasn’t much of a princess type growing up, but if someone had told me that all it takes to go from rags to royalty is five drinks on a Monday, I would have started much earlier.