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 dated IRL from 2007 to 2010.
“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,” Lively told 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.”
Executive Joshua Safran went on to tell Vanity Fair that Lively and Badgley “kept their breakup hidden from the crew,” as they “did not want their personal drama to relate to the show.”
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 before splitting for good in 2010.
Scroll through for a breakdown of the Gossip Girl cast’s love lives:
Credit: Image Press Agency/NurPhoto/Shutterstock
Blake Lively
Following her romance with Badgley, Lively was infamously linked to Leonardo DiCaprio for a whirlwind romance in 2011. “When I think about shooting the L.A. episodes, Blake was dating Leo at the time,” Joshua Safran told Vanity Fair, referring to the two episodes of Gossip Girl season 5 set in California. “She had this thing where she had a doll that she took photos of that she sent to Leo.”
Lively started dating now-husband Ryan Reynolds after meeting on the set of 2011’s Green Lantern. They wed in September 2012 and share three daughters: James (born in 2014), Inez (2016) and Betty (2020). The couple welcomed their fourth baby, son Olin, in February 2023.
Credit: Gregory Pace/Shutterstock
Leighton Meester
Another on set romance, the actress who played Blair Waldorf was linked to guest star Sebastian Stan, who played Carter Baizen on several episodes of the CW series from 2007 to 2010. When asked about Meester’s steamy scenes with onscreen love interest Ed Westwick in 2009, Stan replied, “It’s work and everyone shares the same mentality when it comes to that. But we all laugh about it. The good part is I get to go home with her.”
While she was briefly linked to her Country Strong costar Garrett Hedlund in 2011, Us Weekly broke the news in 2014 that she had secretly married Adam Brody. The pair have appeared together on screen in multiple films, but fans are more fixated on the fact that they both appeared in iconic Josh Schwartz teen dramas, with Brody playing Seth Cohen for four seasons on The O.C. The couple share daughter Arlo (born in 2015) and a son — whose name they haven’t publicly announced — born in 2020.
Credit: Chris Pizzello/Invision/AP/Shutterstock
Penn Badgley
When asked about his best and worst onscreen kisses on WWHL in 2015, the You star named Lively for his best (while they were dating) and his worst (when their characters got back together after their split).
Badgley dated Zoë Kravitz from 2011 to 2013 before exchanging vows with Domino Kirke in 2017. The duo welcomed son James in August 2020. They are currently expecting twins. The Easy A star is also the stepfather of Kirke’s son Cassius.
Credit: Kathy Hutchins/Shutterstock
Chace Crawford
While he often stays mum on his personal life, Crawford has been linked to Carrie Underwood, model Rachelle Goulding and Rebecca Rittenhouse. Us broke the news in 2019 that the Blood and Oil costars quietly split after three years together. While they were spotted together on vacation during summer 2021, they never publicly confirmed or denied that they were back on.
Credit: Scott Garfitt/AP/Shutterstock
Ed Westwick
Despite his public declarations of love for Meester, the twosome seemingly never dated for real. In addition to his romance with Szohr, Westwick has been linked to models Jessica Serfaty and Tamara Francesconi.
The Wicked City alum was accused of sexual assault by multiple women in 2017. After denying the allegations, Us confirmed in 2018 that Westwick would not face charges due to insufficient evidence.
Westwick began dating actress and model Amy Jackson in 2021 and popped the question in January 2024. “Hell YES 💍,” Jackson captioned Instagram pics of their proposal. Westwick wrote that he “hit the jackpot” via his Instagram Story at the time. The pair traveled to Italy ahead of their Amalfi Coast nuptials that August. Later that month, Westwick and Jackson said “I do.”
