Spotted: the most scandalous Upper East Siders settling down IRL. Blake Lively, Leighton Meester, Penn Badgley and more Gossip Girl cast members have settled down after skyrocketing to fame on the beloved drama.
During the series’ six-season run, however, there were several on set romances. While portraying on-again, off-again couple Serena and Dan, Lively and Badgley began a real-life relationship.
“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,” the Sisterhood of the Traveling Pants star recalled to Vanity Fair in 2017. “[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.”
The pair dated from 2007 to 2010. “Some would say it’s a double-edged sword, but in our case, we manage to balance it well,” he told Us Weekly exclusively in 2009 about navigating their relationship while working together.
Executive Joshua Safran recalled learning about their split in the Vanity Fair profile.
“They kept the breakup hidden from the crew, which you could never do now,” he said. “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.”
Chace Crawford shared a similar sentiment when asked by Andy Cohen in 2019 whether “Blake Lively and Penn Badgley’s real life relationship and breakup cause drama amongst the cast?”
“Not at all. Not in the least,” the Boys star said on Watch What Happens Live With Andy Cohen at the time. “Most mature people in the world.”
Lively and Badgley weren’t the only ones to mix business with pleasure on Gossip Girl. Ed Westwick (Chuck Bass) dated Jessica Szohr (Vanessa Abrams) on and off through the series run.
“It can be a little awkward when all of a sudden [you have feelings for] someone you’d call to talk about a different boyfriend,” Szohr told Teen Vogue in 2009. “But there wasn’t a lot of thinking and talking. It kind of just happened. We had fun together, and we were like, ‘All right, let’s see where this goes.’”
The duo split for good in 2010.
Scroll through for a breakdown of the Gossip Girl cast’s love lives:
