Here Are The 10 'Gossip Girl' Actors Who Dated Each Other IRL

On Gossip Girl, Blake Lively and Penn Badgley played on-and-off-and-on-again couple Serena van der Woodsen and Dan Humphrey, and the actors also dated on-and-off IRL between 2007 and 2010. After the two split, they managed to hide their breakup from the rest of cast for several months, which is impressive AF. "They kept the breakup hidden from the crew, which you could never do now," executive producer Joshua Safran told Vanity Fair. "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."

During a May 2013 interview with Elle, Badgley was asked whether it was difficult to work with Lively after their breakup, and he said they were "ultimately professional" together, adding, "We were very much caught up in the show, which itself was a six-year endurance test. Our relationship was a part of that and helped us through it. I mean, like anything valuable, it was good and it was bad and it was a learning experience."

Later, when Badgley appeared on Watch What Happens Live With Andy Cohen in March 2015, a caller asked the actor which cast member he enjoyed kissing the most on screen and who he enjoyed kissing the least. His answer for both: Lively. "I'd say best... I'll say it was Blake, because we actually had a relationship at the time," he said. He then jokingly adding that the worst kiss was "maybe Blake after we broke up," though he noted they both handled the situation well. "We should both pat ourselves on the back because anything is complicated in that way... and we handled it," he added.

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.