According to Andy Dunn, founder of the online fashion retailer Bonobos, “We’re a long way from pants.” Now, the former CEO is undertaking a new challenge: helping people form friendships. In an interview with TechCrunch, Dunn discussed his latest venture, which aims to bring individuals together in real life.

Dunn’s latest startup, Pie, is a social app designed to facilitate in-person connections among users. The platform has secured an $11.5 million Series A funding round, enabling it to pay organizers to host events. As a result, Pie has garnered over 130,000 monthly active users in San Francisco and Chicago, despite being available in only these two cities. However, the increasing number of users has led to more crowded events, making it challenging for individuals to connect with each other.

The company is facing a dilemma: when hundreds of people attend an event, it can be difficult for guests to determine who to engage with, making it hard to form meaningful connections. Dunn noted, “This is the beauty of building a startup – a solution often creates a new problem.” Fortunately, a potential solution to this issue was not difficult to find.

Two event organizers on Pie, Samir Mahafzah and Sam Stubbs, were already developing a tool called Sparked Connections, which utilizes AI to predict compatible individuals at social events. Pie acquired the founders and integrated the quiz into select gatherings, branded as “Sparked by Pie.”

For instance, at Pie’s “Coffee with Strangers” event, attendees are required to take a short personality test before the gathering. The test asks respondents to rate their level of agreement with various statements on a scale of 1 to 5, covering topics such as willingness to pursue a passion, beliefs in astrology, and voting habits. The algorithm then divides the respondents into groups of six, based on their predicted compatibility, and places them in a group chat on Pie, allowing them to get acquainted before the event.

Dunn explained that the quiz’s algorithm is being powered by ChatGPT, and as the platform receives feedback on user connections, it will gain insights into what makes people compatible. He noted, “I think that’s such a complex issue that without the AI inflection point, it would be almost impossible to solve.”

As concerns about Americans’ increasing loneliness continue to grow, it may seem disappointing that we require algorithms to facilitate friendships. However, if you’ve ever connected with someone on Instagram or used a dating app like Bumble, you’ve already allowed AI to play a role in your social life.