• I tried Pie Social, a million-dollar app that encourages socializing through in-person meetups.
  • It’s being tested in Chicago right now, so I attended three events through the app.
  • The app makes meetups accessible but isn’t exactly groundbreaking — it’s mostly a directory.

Making friends is apparently a million-dollar problem — and the latest app trying to solve it is Pie Social.

The Chicago-based startup was founded by Andy Dunn, cofounder and former CEO of the menswear brand Bonobos. As of October, Pie reported it’s raised about $24 million in capital.

Its goal is clear: “Make it easy to make friends,” Dunn wrote on LinkedIn in October.

“We are building a social app to combat this problem. The job to be done is to make it easy to make friends,” he wrote. “Our vision is for a world where doing things you enjoy with people you like should be as easy as calling an Uber.”

Since the app is being tested in Chicago, where I live, I decided to see how effective Pie Social is in finding community, especially among social circles I wouldn’t normally gravitate toward.

So, I downloaded the app and used it for a few days. Here’s how it went.

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