Penn Badgley's Short Dating History Includes Blake Lively and Zoë Kravitz

Badgley and Lively famously starred as Dan and Serena on "Gossip Girl," and their onscreen chemistry extended into the real world for a bit while they were on the show. The pair had an on-and-off-again relationship starting in 2007, even making their red carpet debut at the 2018 Met Gala together, though they officially broke up in 2010.

Lively, of course, is now married to Ryan Reynolds, and the couple recently welcomed their fourth child together.