Andy Dunn, the former CEO of online fashion retailer Bonobos, has embarked on a new venture that's far removed from the world of pants. Dunn's latest startup, Pie, is a social app designed to bring people together in real life, tackling the growing concern of loneliness in the process.

Pie has already made significant strides, securing an $11.5 million Series A raise and amassing over 130,000 monthly active users in just two cities, San Francisco and Chicago. The app's growth has been fueled by its innovative approach to hosting in-person events, which are organized and funded by the company. However, as the user base expands, Pie faces a new challenge: how to facilitate meaningful connections between attendees in crowded event settings.

This conundrum is a common problem in the social app space, where users often struggle to find common ground with strangers in large groups. To address this issue, Pie has turned to AI-powered solutions. The company has acquihired the founders of Sparked Connections, a tool that uses personality quizzes to predict compatible connections at social events. This technology has been integrated into certain Pie events, dubbed "Sparked by Pie," which aim to create more intimate and meaningful interactions between attendees.

The Sparked Connections quiz is a short, 10-question personality test that asks users to rate their agreement with various statements on a scale of 1 to 5. These prompts cover a range of topics, from willingness to take risks to beliefs about astrology. The algorithm then divides respondents into groups of six, based on their compatibility, and places them in a group chat on Pie before the event. This allows attendees to get to know each other beforehand, increasing the chances of forming genuine connections.

Dunn believes that AI is essential to cracking the code of human connection. "We're starting to power it through [ChatGPT]. And then when we get feedback loops of who connects with who, and who invites people to stuff, we'll start to see, well, why do people hit it off?" he explained. "And I think that's such a dark art that without the AI inflection point, I think it would be an almost unsolvable problem."

The rise of Pie and its AI-driven approach to social connections raises important questions about the role of technology in our personal lives. While it may seem counterintuitive to rely on algorithms to form friendships, the reality is that many of us already use AI-powered platforms to connect with others, whether it's through social media or dating apps. As concerns around loneliness and social isolation continue to grow, Pie's innovative approach may be a vital step towards building more meaningful relationships in the digital age.

In the broader context, Pie's success could have significant implications for the social app landscape. As users increasingly crave more authentic, in-person connections, startups like Pie are well-positioned to capitalize on this trend. With its unique blend of AI-powered matchmaking and in-person events, Pie may be the key to unlocking a new era of social connection and community-building.