Gossip Girl is at it again. Spoiler alert from more than a decade ago, but Dan Humphrey, aka Lonely Boy, aka Penn Badgley turned out to be the titular anonymous blogger and pot stirrer on Gossip Girl. And his time off the show was honestly just as interesting; he was dating his co-star Blake Lively.
Blake played Serena van der Woodsen, and at the same time that Serena and Dan were dating on the show, Blake and Penn were dating in real life. If that sounds like it might have been emotionally confusing to try to separate real life from fictional life, well, you’re not wrong. Penn just sat with Alex Cooper on Call Her Daddy and talked about how he lacked the “emotional maturity to understand how to differentiate” himself from Dan “in terms of self-worth.”
In 2017, Blake talked to Vanity Fair about how his and Blake’s professional and personal lives got all mixed together. “I remember there was one point where we were just afraid of how our personal lives overlapping our work life could be perceived by our bosses,” she said. “[But then] we were like, ‘Oh no, that’s exactly what they want.’ They wanted us all to date. They wanted us all to wear the same clothes that we’re wearing on the show. They wanted that, because then it fed their whole narrative. People could buy into this world.”
It honestly sounds like it must have been pretty confusing. Let’s break down Penn Badgley and Blake Lively’s relationship timeline to try to understand.
Penn Badgley And Blake Lively’s Relationship Timeline
September 2007
Gossip Girl premiered in the fall of 2007, and around the same time, relationship rumors started swirling around Penn and Blake. Even though they didn’t confirm it publicly at the time, later they said this is when they started dating.
January 2008
Blake denied an off-screen romance with Penn when she spoke to PEOPLE. “Everybody always tries to dig into your personal life or create things that aren’t there … It’s silly,” she “Any male friend is obviously a ‘romance alert’ [for the media], but I’ve always been friends with boys my whole life.”
May 2008
But by spring 2008, the truth came out when PEOPLE published photos of Blake and Penn kissing in Mexico. There were a bunch of other photos of them looking very cozy and couple-y.
August 2008
Blake and Penn attended the 2008 Teen Choice Awards with their whole Gossip Girl cast, but the two of them were especially touchy-feely with each other while at the show.
Spring 2009
A lot of reports say Blake and Penn broke up in 2010, but according to Gossip Girl executive producer Joshua Safran, their breakup actually happened in spring 2009. “I found out on the set of the season 2 finale that Blake and Penn had broken up months before,” he told Vanity Fair in 2017. “They kept the breakup hidden from the crew, which you could never do now. I don’t even know how they did it. They kept it from everybody, which is a testament to how good they are as actors. Because they did not want their personal drama to relate to the show.”
October 2010
They officially confirmed their breakup in October 2010, over a year after they allegedly actually broke up. But probably the hardest part is that they kept working together through the end of Gossip Girl in 2012.
