Blog Get in the (cupcake) van: The A.V. Club rides along with Flirty Cupcakes

It's easy to hate the concept of a cupcake truck. It relies heavily on three sometimes-obnoxious trends—gourmet cupcakes, street food, and social media marketing—and seemed to gain popularity soon after Andrew “Dice” Clay and Dennis Rodman cruised around in one in an episode of Celebrity Apprentice last year. To make matters worse, the names of these cupcake vendors-on-wheels also tend to be sickeningly cute: Curbside Cupcake, Love'n Cupcakes, Cake & Shake, etc. As for the price of these diminutive cakes-in-a-cup? Pretty pricey for recession-frosted consumers—Chicago’s first mobile-cupcake business, Flirty Cupcakes, charges $3.25 a frosted pop. Still, when Flirty invited The A.V. Club along for a ride-along earlier this week in its second week of operation, who were we to begrudgingly resist?

But by the end of my ride-along, I felt my skepticism melt away. It's hard to be Scrooge when nearly everyone who encounters Flirty acts like Tiny Tim on Christmas Day.

Although I hitched a ride with full-time driver Jessica Burton, the bright blue Flirty van is actually the brainchild of husband and wife Chris Sewall and Tiffany Kurtz. Kurtz said she spied an old, beat-up ice-cream truck in her neighborhood last year and thought it could be fun for city dwellers if they upgraded it with another kind of sugary treat—the cupcake. Getting through all of the city's red tape of required permits and regulations wasn't easy. Kurtz spent several months and thousands of dollars investing in requirements like a running sink and mobile refrigerator for the van to finally shift Flirty Cupcakes out of neutral.

Like most cupcake trucks in other major cities, Chicago's doesn't have a set schedule. It tweets several of its scheduled stops for the day—and also posts them on Facebook—and leaves the rest to serendipity. As a result, Flirty customers can be neatly divided into two different camps. There's the random foot traffic that happens to stumble upon it, and the Facebook or Twitter-enabled foodies who track down the truck like they might find the pot of gold at the end of a rainbow.

Some wanderers who spotted the truck chuckled and moved on or seemed to intentionally get out of its wake. Others stopped suddenly in their tracks and marveled: "Oh my!" exclaimed a startled nurse who actually lifted her hand over in mouth in shock.
Ryan Smith

A twee, professorial-looking man named Frank even briefly lost his expression of studied disinterest and seemed to completely lose his shit. "Do my eyes deceive me?" he said before purchasing four of the seven kinds of cupcakes: the Devil In Disguise (red velvet), a Curious George (banana-chocolate with salted caramel buttercream icing), the chocolate chip and cream cheese-engorged McDreamy, and the PB&C (chocolate with peanut butter ganache).

On our second stop in front of Al's Italian Beef (1079 W. Taylor St., 312-226-4017), a rugged-looking vendor swooped in to open up his jangling ice-cream cart. “What do you think of the competition?" I inquired. "No, no. It's good. I like the cupcakes," said the ice-cream man in a thick eastern European accent. Burton tapped out a tweet about it.

We ran into more of the second kind of Flirty customers, the social-media devotees, at the stop at Al's. Two 20-year-old college girls from Michigan sprinted up to the truck and exhaled in a simultaneous sigh. "Finally, we've been looking all over for you!" The pair had been following Flirty Cupcakes on Twitter and trekked all the way from West suburb Oakbrook Terrace earlier that morning to find the van. Were the $3.25 cupcakes worth the hours of racing on the Blue Line and sprinting down Taylor Street? "Every penny," said one of the pair.

This seemed strange to me. I sampled a Devil in Disguise and found it tasty, but similar to the wares sold in other cupcake boutiques. But perhaps that's not the whole point. 

"It's an adventure," Burton says. "It's the game that keeps people intrigued. They don't know when they'll see us again and so it feels special."

I can't argue with that logic after spending the day with Flirty Cupcakes and witnessing grown adults act like grade-schoolers who'd been told there'd be an extra recess or a pizza party. Maybe I personally wouldn't go into catatonic shock after a surprise encounter with the van, or ride the CTA an hour to track it down, but I'm not its target market: I'm content with the Hostess three-pack of cupcakes for $1.39 at the 7-Eleven. But that doesn't mean I'm not glad Flirty Cupcakes is here in Chicago, spreading high-calorie joy in the form of individually wrapped sugar cakes.