Who Dated Who on 'Gossip Girl'? All About the Show’s On

01 of 05 Blake Lively and Penn Badgley Lively and Badgley took their on-screen romance to real life early on during filming, with sparks flying between the two when the show started in 2007. Fans of the show quickly became as invested in the pair's real romance as they were in their character's love story.

"It was a little bit night and day," Badgley told Variety in February 2023 while reflecting on how quickly the cast skyrocketed to fame. "Beyond our relationship, I don't think anybody was going to be interested in me publicly."

Despite the struggle of sudden fame and being in the spotlight, Badgley admitted that dating Lively prevented him from going down a dark path.

"Blake didn't drink, and I think our relationship in some ways saved me from forcing myself to go down that road," he said.

Though they broke up halfway through the show 's run in 2010, Badgley has looked back at the relationship fondly — and admitted that their breakup didn't cause any tension as they continued to work together.

"We were always very professional," he said in a September 2023 episode of Podcrushed . "I don't even think, in my memory, there was not one bit of strangeness. It wasn't even a thing."

Now, Badgley has been married to his wife, Domino Kirke , since 2017 and the two welcomed a son together in 2020. Lively, meanwhile, met Ryan Reynolds shortly after she and Badgley broke up and married the actor in 2012 . The pair share four children : James, Inez, Betty and Olin.

of 05 Leighton Meester and Sebastian Stan Though Sebastian Stan played Serena's on-and-off love interest Carter Baizen in guest appearances between 2007 and 2010, in real life, he dated Meester. The two were first rumored to be together when Page Six reported that they were seen getting cozy with one another at an event in May 2008.

Stan eventually confirmed their relationship in a 2009 interview with PEOPLE, stating that he was a "really lucky guy" because he got to "go home with her."

"She's the most interesting, sophisticated, talented and an extremely funny person that I know. She's really hilarious," he said.

However, by the spring of 2010, the two had called it quits, with Meester opening up about the breakup in an interview with Seventeen later that year.

"I've only had one experience where it was really hard and I was really sad when it ended, but that's what taught me a lot about myself and love and life — and that's good," she said of her romance with Stan.

The relationship was equally as meaningful to Stan, who told Variety in September 2024 that filming Gossip Girl was " the first time I was in serious love with somebody," though he didn't name Meester.

"Walking around the city, seeing these same buildings and streets — life seemed simpler," he said.

Meester went on to meet her husband , Adam Brody , in 2011, and the two started dating in 2013 . Now, they've been married since 2014 and share two children , daughter Arlo and a son, together.

of 05 Ed Westwick and Jessica Szohr Westwick and Jessica Szohr 's characters Chuck and Vanessa were on-and-off flames in the show, and, in real life, the two had chemistry between them as well. When the actors first started dating in 2008, they attempted to keep their relationship private.

Szohr recalled on a February 2022 appearance on the Chicks in the Office podcast that after keeping things lowkey in the first few months of their relationship, they grew restless and wanted to attend an NBA game together, despite the unwanted attention it would bring.

"Either we are going to live this private life and never leave our apartment, or we do it and we just keep our s- as private as we can," Szohr recalled them deciding.

The two broke up a number of times throughout their relationship, but called it quits for the final time in 2010.

In their personal lives since, Szohr welcomed daughter Bowie Ella Richardson in January 2021 with former Vancouver Canucks player Brad Richardson, whom she married in August 2024.

Westwick tied the knot with his wife, Amy Jackson , that same month after dating for three years.

of 05 Taylor Momsen and Chace Crawford In the first season of Gossip Girl, Dan's little sister, Jenny Humphrey ( Taylor Momsen ), has a crush on her idol Blair's boyfriend, Nate Archibald ( Chace Crawford ).

Later in the show, the two briefly date. However, in real life, Momsen has denied that anything happened between herself and Crawford, despite reporting that they may have shared a kiss, per Page Six .

"It's great, because going to set we're all such good friends. And you know, rumors are rumors," Momsen told OK! in March 2009 after shutting down the possibility that she was dating Crawford.

In June 2024, Crawford confirmed during an appearance on Call Her Daddy that he had hooked up with one of his costars but wouldn't share which one.

"I would say those things are inevitable," he said. "When you're in your 20s ... the thing is you're on these things ... It's the downtime. You're doing this show, you're on set for like 12 to 14 hours a day, and usually there's some pretty interesting people from all walks of life."

of 05 Kelly Rutherford and Matthew Settle As another couple that had a romantic storyline throughout the six seasons of Gossip Girl, Kelly Rutherford and Matthew Settle (who played Serena's mom Lily and Dan's dad Rufus) were often rumored to be in a relationship themselves.

In 2010, both Settle and Rutherford split from their partners and were undergoing divorces, leading fans to tie the two together. At the time, Settle denied the rumors to PEOPLE, explaining that they're just "good friends."

"Kelly and I have a lot in common because we are supporting each other at this time in our lives," he said.

In 2014, Rutherford made a number of Instagram posts with Settle, including one of her kissing him on the cheek and her leaning against his shoulder , causing fans to suspect their relationship was more than friendly once again.

However, the two never clarified their relationship past that point and have seemingly remained close friends since.