“This feels like a basement,” my friend Jenny said as our group settled into a cluster of chairs at Watershed, the new River North bar tucked below Pops for Champagne that serves wine, beer, and spirits solely from the Great Lakes region. It was the kind of remark that doesn’t bode well when you’re trying to give a place a snark-free shake. “It is a basement,” I told her. “But don’t you think it’s kind of cozy, like being at your grandma’s or something?”

“Yeah, if my grandma lived in a retirement community,” Jenny retorted, eyeing the carpeted floors and upholstered armchairs. Maybe she had a point, but since my own first impression of Watershed was more comfy-hospitable than convalescent home, I was willing to work to convince the others. I directed my friends’ attention to the drink menu and recommended a favorite from a previous visit, the Shake in the Hay (a concoction involving Lake Bluff’s North Shore gin; $10), then reminded them that the Northside Southpaws, a guitar-and-mandolin duo, were set to play shortly. “It’ll be like an urban hoedown!” I enthused.

At 7 p.m. on a Thursday, Pops’ once-dead jazz room was abuzz with afterwork chatter. We’d snagged the last few seats in the house and waited patiently for our first round of cocktails, including a Moscow Mule (Crop cucumber vodka, Koval ginger liqueur, lime juice, and ginger beer; $10) for the doubting Jenny, who pronounced the drink “good—really good.” Also on order: a bowl of Brussels sprouts, a few mussels, and—worth a visit alone—some crispy marble potatoes fried in duck fat ($3). “When’s the band coming on?” my friend Sean asked a little anxiously as he peered at the musicians lounging at a nearby table, instruments safely encased.

“Supposed to be nine,” I said, checking my BlackBerry and weighing the cost of another $10 cocktail as the loosened-tie/chic-heeled crowd started to trickle out the door. A switch to beer—all featured brews hail from Illinois, Indiana, Ohio, Wisconsin, and Michigan—bought us some time, and we entertained ourselves by reminiscing about basement bars of the past (RIP, Katacomb) and speculating whether a pair of attractive blonds with atrociously awkward body language were on a first date (confirmed). But when I found myself gazing at yet another empty drink in a half-empty room, we signaled for the check and gathered our bags.

Turns out the Southpaws don’t play until 10 p.m.—a time I’d suggest tweaking. This is a business district after all, and happy-hour drinkers prefer early retirement.

Watershed 601 N. State St.; watershedbar.com

Photograph: Chris Guillen