When the Popsicle Princesses arrive at the Time Out Chicago offices for an interview, they immediately hoist a picnic basket and distribute their wares—the Gloria Gaynor (whole blueberries, lemon zest and juiced berries), the Madonna (strawberry and basil syrup), the Kathleen Hanna (mango with a hit of cayenne)—to passersby in the foyer. “Would you like a pop?” they ask me. A hand-labeled, multicolored fruit pop made by two women wearing matching red gingham shirts and cutoffs? Only David Brooks is a big enough killjoy to refuse.
The Popsicle Princesses are Liz Wolferman and Emma Nolley, a renegade pair of 23-year-olds whose mission is to bring ice pops, made in batches of 30 and transported in that picnic basket on the back of a sometimes-functioning tricycle, to the streets. Their role model: the tamale guy. “We were just fed up with the laws of vending in Chicago,” says Nolley, “and we were like, You know what, those tamale guys are out there doing it, and we love that, and they go to the bar, run around, and everyone gets so excited. Can we do that, too?”
The paleta men don’t need to fear for competition in city-park territory, though. Since May, the Popsicle Princesses have been setting out late night (around 10pm) to Boystown and Andersonville. “We have a tag,” Wolferman explains: “A gal on a trike and a dyke on a bike: I’m the dyke on the bike; Emma’s the gal on a trike.” ("We're never going to be able to afford a truck," Nolley says.) As part of their girl pride, their pops—made from pureed fresh fruit and herbs grown in Wolferman’s garden—pay homage to female icons. “We sat down and we were like, ‘Who personifies each flavor?’” Wolferman says. Hence the Lady Gaga, which layers all the other flavors into one crazy pop. And though the hot afternoon seems like Popsicle hour, Wolferman and Nolley see the craving differently: “Standing in line at a bar is so boring; why not eat a Popsicle?” asks Nolley. “Leaving a bar at night, you’re hot: Popsicle!”
Despite all their excitement, the Princesses know what they’re doing could hold consequences bigger than accidentally napping in a room with dry ice. “It’s kind of an experiment to see what boundaries we can push,” Nolley says. “Maybe we can set some sort of positive example.” The pair have sanitation certificates and a peddler’s license, but legally that license allows them to sell only whole fruit. So why have it at all? “It’s a little bit of security,” says Wolferman, so “we [can be] like, oh, don’t worry, we can totally sell these. And if anyone really questions hard enough, we would just…” And with that, Wolferman motions to Nolley to get on the trike.