On a normal Friday, I’d have drinks at a dive like the Sunnyside Tap (4410 N Western Ave), where potbellied men show you wallet photos of their grandchildren festooned in Bears gear, but Tamia suggests we start with art openings, since Chicago’s gallery scene offers myriad opportunities for free hooch. (See Art & Design and Around Town for more info.)

7:30pm
Standing outside in the gallery district
Hipsters fear no open-container laws, so we find them milling around smoking and drinking Schlitz outside the 40000 Gallery (119 N Peoria St, 312-738-0179). Since I didn’t down my customary drinks beforehand, I feel socially awkward and avoid eye contact with acquaintances. As we make our way inside, Tamia gets halted by a girl in a blue vintage dress who’s holding a beer in one hand and a teacup terrier in the other. Tamia quietly informs me that last weekend she ended up at the girl’s house and in the middle of a late-night movie, the terrier’s member became very prominent. The girl, uh, took care of it, so he wouldn’t “become aggressive.” I normally need a stiff drink before conversations about bestiality, so we quickly make for the gallery.
Lesson 1: If you’ve got booze sitting around at home, hit that before you go out. There are some real strange ones out there.

7:45pm
Inside 40000 Gallery
The gallery is packed. Inside, L.A. artist Nathan Redwood has created a seaworthy wooden ship decked out with a chandelier. I spot the free beer and weave through the crowd only to find that the Grolsch has a suggested donation sign next to it. But as I’ve learned from my therapist, a suggestion is only a suggestion, so I ask for two beers. Stuffing the extra beer into my purse, I figure I’m set for the next hour or so.
Lesson 2: When it comes to free beer, ignore your conscience and hoard what you can.

8:15pm
The beer supply is depleted, so people flee the space. We decide to take a risk and head to another gallery.

8:20pm
The Charles LaBelle show at Bodybuilder & Sportsman
The gallery (119 N Peoria St, suite 2C, 312-492-7261) is practically empty, but I spy three lone PBRs on a counter. Between the beers and me is a guy with thick tortoise-shell glasses who appears to work at the gallery. I beg him for a beer and he hands me a single sweating can. I decided to push my luck. “Actually can I have two?” He grins knowingly and hands me another. I give Tamia a beer and meditate on the digital quilts of color until I see Tamia with a puddle of still-foaming yellow liquid on the floor in front of her. “I dropped my beer…what do I do?” she whispers. Deciding that we’ve overstayed our welcome and worrying that these art lovers are onto us, I figure it’s time to make a break for it. “Just walk away,” I hiss. And that’s exactly what we do.
Lesson 3: Know when to cut your losses.