‘Gossip Girl’ Cast’s Dating History: On Set Romances, Crossover Marriages

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‘Gossip Girl’ Cast’s Dating History: Blake Lively, Leighton Meester, Penn Badgley and More

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.”

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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:

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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 actress is currently expecting her fourth child. 

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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.

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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. The Easy A star is also the stepfather of Kirke’s son Cassius.

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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.

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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.

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Jessica Szohr

In addition to her relationship with Westwick, Szohr dated Aaron Rodgers — twice. After a brief relationship in 2011, Us broke the news in 2014 that they were giving it another go before things fizzled again. Szohr was subsequently linked to Scotty McKnight before she started to see hockey player Brad Richardson. The actress and the athlete welcomed daughter Bowie Ella Richardson in January 2021. In May 2022, Szohr announced that she and Richardson are engaged. “I said yes!” she wrote via Instagram at the time.  

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Matthew Settle

While working on the series, Settle and wife Naama Nativ, who share daughter Aven, called it quits. News broke of their divorce in 2010. Rumors subsequently ran wild about the Gossip Girl dad and Kelly Rutherford dating IRL, but the close costars always referred to each other as friends. After he officially moved on with Maria Alfonsin in 2014, they welcomed a daughter named Nalu in 2015.

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Kelly Rutherford

The GG mom was briefly married to Carlos Tarajano from 2001 to 2002. She wed Daniel Giersch in 2006 and welcomed two kids: Hermés and Helena. Following their split in 2008, the former couple were involved in a lengthy custody battle as they lived in different countries. Us broke the news of her romance with screenwriter Chiswell “Chum” Langhorne in September 2018.

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Taylor Momsen

The youngest of the GG bunch, the Pretty Reckless songstress has kept her private life under wraps. She was briefly linked to Paul Weller’s son Natt in 2011.