If you're a true Gossip Girl fan, then you know just as much drama went down behind the scenes as it did on the series. Over the course of the show's six-season run, there were rumors of feuds, disputes, and diva behavior, and — as you'd expect when you put a bunch of ridiculously good-looking actors together — a lot of juicy hookups. Though it's still unclear how many Gossip Girl actors dated each other IRL and how many were only rumored to be dating, it's clear that co-star romances were prevalent. In fact, according to Blake Lively, those off-screen hookups were actually encouraged by production.
"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 during an August 2017 interview, "[but then] we were like, 'Oh no, that's exactly what they want.' They wanted us all to date ... They wanted that, because then it fed their whole narrative. People could buy into this world." Well, congrats, team, because it definitely worked.
Gossip Girl herself (or, well, himself) may be the only one who knows exactly what went down behind the scenes, but here are the biggest GG cast hookups you should know about.
Jessica Szohr and Ed Westwick — who played occasional lovers Vanessa Abrams and Chuck Bass — also developed a casual relationship off screen. The two dated on-and-off between 2009 and 2012, though Szohr left the show as a series regular in 2011 after its fourth season.
It seems the two remained good friends even after their split. Five years after Gossip Girl ended, Westwick was accused of sexual assault by several women, and during a November 2017 interview with Cosmopolitan, Szohr said she found the accusations "shocking," especially since she and Westwick still had a close relationship.
"...I have known Ed for years and know how lovely he is, and don't think he would ever put someone in a position like that," she said, later adding, "From the Ed I know and working with him for five years and having a friendship through all of that and after, it was shocking." (Westwick later denied the accusations, writing in a since-deleted tweet, "I have never forced myself in any manner, on any woman. I certainly have never committed rape." In July 2018, the L.A. County District Attorney's Office announced it was declining to file charges against Westwick.)
Dating rumors started swirling around Leighton Meester and Sebastian Stan — who played one-time lovers Blake Lively and Carter Baizen — after a source for Page Six claimed the two actors "couldn't keep their hands off of each other" while having an industry dinner in May 2008. The following year, Stan told People that the best part about working with Meester is that he gets to "go home with her" after the director yells cut, making their relationship status clear. "I'm a really lucky guy," he added. "She's the most interesting, sophisticated, talented and an extremely funny person that I know. She's really hilarious."
The couple reportedly dated for just about two years before going their separate ways in April 2010. At the time, a source for OK! magazine claimed Meester broke up with Stan because she didn't "know how to be in a relationship and doesn't really like them." Meester seemingly confirmed this when she told Seventeen that being in a relationship wasn't really her style. "I've never really liked anybody before," Meester explained in January 2011. "Even when I would date guys, it would sort of be on the surface and it was always a relief when we broke up."
Though Taylor Momsen and Chace Crawford — who played short-lived couple Jenny Humphrey and Nate Archibald — never officially dated (as far as fans know, anyway), the two reportedly hooked up back in December 2008. A source for Page Six claimed the actors were reportedly caught kissing during their cast holiday party (and reportedly, that wasn't the only time the two were spotted hooking up). However, when asked about the dating rumors by OK! in March 2009, Momsen denied them. "It's great, because going to set we're all such good friends. And you know, rumors are rumors," she said.
Fans still aren't sure what the deal is with Kelly Rutherford and Matthew Settle, who played on-screen lovers Lily van der Woodsen and Rufus Humphrey. After Rutherford and Settle announced the end of their respective marriages around the same time in 2010, fans began speculating that the actors were an IRL item. However, the two insisted they were merely friends who relied on each other for support. "We're good friends," Settle told People in March 2010. "Kelly and I have a lot in common because we are supporting each other at this time in our lives."
The actors may have denied dating claims, but they definitely kept the rumor mill turning with their many social media posts and cozy red carpet appearances. In October 2014, Rutherford and Settle dating rumors hit a fever pitch when the two suddenly ramped up their social media affection. Sadly, the pair has never clarified whether they were ever an actual couple, but based on this March 2020 Instagram post from Rutherford, I'd say the two are still tight.
Here's hoping the HBO Max Gossip Girl reboot delivers just as much off-screen drama.
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