OkCupid

Founded in 2004 by Harvard math whizzes Christian Rudder, Chris Coyne, Sam Yagan and Max Krohn, OkCupid took the online dating world by storm with an algorithmic approach to love that promised to turn data into desire. The site’s quirky questions and freewheeling attitude quickly attracted millions of users, making it a pioneer in the democratization of online matchmaking. Yet, the company wasn’t without its controversies—Rudder’s candid revelations about user data manipulation in his book 'Dataclysm' sparked debates on privacy and ethics. In 2011, Match.com acquired OKCupid for $50 million, folding it into the conglomerate’s portfolio of love factories. Under Rudder’s continued leadership, the platform maintained its relevance in a market saturated with swipe-based apps, though critics argue its original charm has faded with commercialization. OkCupid’s legacy? A trailblazer in the world of digital romance, it proved that algorithms could indeed be Cupid’s modern arrow, albeit with a few ethical strings attached.