Social Startup 222 Raises Millions to Expand Relationship Tech | Invesloan.com

It’d be nice to meet someone the old-fashioned way: Passing by them on the street, meeting at a restaurant, or sharing an exchange at a party.

However, apps dominate the modern dating experience, replacing kismet meet-cutes with scrolling and DMs.

222, a startup focused on relationship building with the help of AI, thinks it can bring back the spontaneity of making a new friend — or falling in love.

“We’re trying to get as close as possible to you walking into someplace with other people there, and connection just naturally happens,” CEO Keyan Kazemian told Business Insider.

At a high level, 222 matches people with strangers for experiences like dinner or a night out after they take a robust personality quiz, using machine learning models trained by its team and open-source AI models.

“When you walk in, all of those people are people we predict you’re going to be able to have a good conversation with, and you’ll like,” COO Danial Hashemi said.

When 222 launched in 2021, it began as a dinner series in Los Angeles for young adults emerging from the COVID-19 pandemic, helping them meet new people. Then the project grew into a company. It was accepted into Y Combinator, raised capital, moved to New York City, and launched a mobile app to spur in-real-life (IRL) socializing.

While people who join 222 are often new to a city, Kazemian said, today they’re pretty evenly split along why they’re using the platform: they’re either looking for new friends or potential romantic connections.

Since putting out its app in 2024, the 222 experience has evolved. It’s no longer just about meeting strangers, having a fun night, and forming new relationships.

“We’re very focused on going beyond that,” Kazemian said.

The platform is now digging deeper into connecting people after the first encounter that 222 initiates. It’s helping plan follow-up hangs with friends and kindling a romantic connection by setting people up on a date if the feeling is mutual.

Simulating the meet-cute

After a 222 experience, the platform follows up to ask attendees whether they want to hang out or go on a date with anyone they met.

Once two people say they’d like to go on a date, “we fully set up the next date for them,” Hashemi said — reservation and all.

“If you think about just before dating apps, before all this stuff, how would people meet each other?” Hashemi said. “It would be you’re in the same physical space with no preconceived notions of who this person is going to be.”

Hashemi said that some of the “joy” of navigating how you feel about someone new in your life has “gone away because of dating apps.”

Meeting in a way that feels more organic, such as a social gathering or through friends, has staying power. A 2025 survey of 7,000 US adults by health company Hims found that 77% of Gen Z met their partners IRL. Even Partiful, the Gen Z replacement for Facebook Events, is getting in on the IRL event-to-dating pipeline.

222 thinks AI can make the meet-cute more accessible.

What 222’s founding team has zeroed in on is “labeled data,” Kazemian said, which comes from its users’ feedback after they meet people.

The startup knows its first pairings may not be the ultimate match, which is why it encourages its subscribers — who pay $22 a month — to try multiple experiences. Its AI, in return, can curate better matches from 222’s network.

There are layers of factors that contribute to that, 222’s CTO Arman Roshannai said, such as similar music tastes or hometowns.

“The signal that we’re training on is after you meet this person, you spend two hours getting dinner with them, and then you hang out for a few hours afterwards, were you guys actually a good match for each other?” Roshannai added.

Kazemian added that training on this proprietary data from user feedback is a “painstakingly difficult and long process,” but gives the startup a “technical moat” to stand out from some competitors.

AI’s new role in relationships

222 isn’t the only startup — or public company — betting that AI can improve how we connect.

Several startups have launched with this premise and are raising millions, pitching matchmaking solutions that use AI to set people up. Meanwhile, Bumble, Tinder, and Facebook Dating are testing the AI waters and reimagining the swipe. Hinge’s founder recently left the Match Group-owned dating app to build an AI dating alternative.

After raising another $10.1 million from venture capital investors in 2025 — bringing the startup’s total raised to $13.7 million — 222 is doubling down on hiring and expanding its product with tools that keep relationships going.

222’s next undertaking is to provide avenues for its users to reach their “next offline moment” together, so they can deepen those relationships.

The startup wants to be in the business of both creating relationships and maintaining them.

“They need to show up at the same place together,” Kazemian said, be it a hangout, a date, or a restaurant reservation. “We can help them figure out what that place is.”