“We’re a long way from pants,” said Andy Dunn, founder of Bonobos, in a chat with TechCrunch. Now, he’s diving into a new venture: helping people make friends.

Dunn’s latest project, Pie, is a social app designed to bring people together in real life.
With an impressive $11.5 million Series A funding, Pie has attracted over 130,000 active users, even though it’s only in San Francisco and Chicago. But as the events on the app grow busier, it can be harder for people to find connections.
The challenge for Pie is clear: When lots of people gather, how can attendees find potential friends? How can they bond in a crowded space filled with strangers?
“This is the beauty of building a startup,” Dunn noted. “A solution creates a problem.”
Fortunately, a solution was already in the works.
Two event planners on Pie were developing a tool called Sparked Connections, an AI quiz that helps match attendees with similar interests. Pie acquired the creators, Samir Mahafzah and Sam Stubbs, and integrated their quiz into specific events called “Sparked by Pie.”
For instance, at Pie’s “Coffee with Strangers” events, each guest takes a fun personality quiz. Attendees rate their agreement with statements like: Are you willing to sacrifice stability to pursue a passion? Do you believe in astrology? Do you pray? Do you vote? Do you have any toxic traits?
Based on the quiz results, an algorithm groups participants into sets of six. These groups are then assigned to a chat on Pie, allowing them to get to know each other before meeting up.
“We’re starting to power it through [ChatGPT]. Once we gather feedback on who connects well, we’ll understand better why some people hit it off,” said Dunn. “Without AI, figuring this out would be really tough.”
With rising concerns about loneliness in America, it may feel odd that we need algorithms to forge friendships. Yet, if you’ve ever made a friend through Instagram or dated via Bumble, you’ve already welcomed AI into your social life.
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