Who Dated Who onGossip Girl? All About the On-Set Romances During the Show (and Which Leads Dated Each Other IRL!)

Mar. 15, 2025

Blake Lively and Penn Badgley attend the Nina Ricci After Party For Met Ball Hosted By Olivier Theyskens and Lauren Santo Domingo at Philippe in New York on May 5, 2008 ; Leighton Meester and Sebastian Stan attend the Parsons Fashion Benefit 2009 Pre-party at Calvin Klein Collection on April 2, 2009, in New York City.Photo:Getty

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TheGossip Girlcast didn’t venture too far when finding love of their own while shooting the show.Known for its salacious drama as Manhattan’s elite Upper East Siders navigate the fragile social hierarchy of high school and their own fluctuating relationships,Gossip Girlaired from 2007 to 2012 and made stars out of its main cast members, includingBlake LivelyandPenn Badgley.The two leads not only made up the most tantalizing on-and-off couple, Serena van der Woodsen and Dan Humphrey, on the show. but they also dated in real life.Lively and Badgley weren’t the only on-set romance.Leighton MeesterandEd Westwick— who played steamy couple Blair Waldorf and Chuck Bass — were also linked to costars (though never to each other, much to fan’s dismay).Here’s everything to know about who dated who on the set ofGossip Girl.

TheGossip Girlcast didn’t venture too far when finding love of their own while shooting the show.

Known for its salacious drama as Manhattan’s elite Upper East Siders navigate the fragile social hierarchy of high school and their own fluctuating relationships,Gossip Girlaired from 2007 to 2012 and made stars out of its main cast members, includingBlake LivelyandPenn Badgley.

The two leads not only made up the most tantalizing on-and-off couple, Serena van der Woodsen and Dan Humphrey, on the show. but they also dated in real life.

Lively and Badgley weren’t the only on-set romance.Leighton MeesterandEd Westwick— who played steamy couple Blair Waldorf and Chuck Bass — were also linked to costars (though never to each other, much to fan’s dismay).

Here’s everything to know about who dated who on the set ofGossip Girl.

01of 05Blake Lively and Penn BadgleyPenn Badgley and Blake Lively during the 2008 Teen Choice Awards at Gibson Amphitheater on August 3, 2008 in Los Angeles, California.GettyLively 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 toldVarietyin 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 theybroke 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 ofPodcrushed. “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 twowelcomed a sontogether in 2020. Lively, meanwhile, metRyan Reynoldsshortly after she and Badgley broke up andmarried the actor in 2012. The pair sharefour children: James, Inez, Betty and Olin.

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Blake Lively and Penn Badgley

Penn Badgley and Blake Lively during the 2008 Teen Choice Awards at Gibson Amphitheater on August 3, 2008 in Los Angeles, California.Getty

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 toldVarietyin 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 theybroke 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 ofPodcrushed. “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 twowelcomed a sontogether in 2020. Lively, meanwhile, metRyan Reynoldsshortly after she and Badgley broke up andmarried the actor in 2012. The pair sharefour children: James, Inez, Betty and Olin.

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Leighton Meester and Sebastian Stan

Leighton Meester and Sebastian Stan sighting on April 30, 2009 in Hollywood, California.Getty

ThoughSebastian Stanplayed 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 whenPage Sixreported 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.

“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 toldVarietyin September 2024 that filmingGossip Girlwas “the first time I was in serious lovewith 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 tomeet her husband,Adam Brody, in 2011, and the twostarted dating in 2013. Now, they’ve been married since 2014 and sharetwo children, daughter Arlo and a son, together.

03of 05Ed Westwick and Jessica SzohrEd Westwick and Jessica Szohr arrive at The Art of Elysium’s 3rd Annual Black Tie Charity Gala “Heaven” on January 16, 2010 in Beverly Hills, California.GettyWestwick andJessica 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 theChicks in the Officepodcast 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 daughterBowie Ella Richardsonin January 2021 with former Vancouver Canucks player Brad Richardson, whom she married in August 2024.Westwicktied the knotwith his wife,Amy Jackson, that same month after dating for three years.

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Ed Westwick and Jessica Szohr

Ed Westwick and Jessica Szohr arrive at The Art of Elysium’s 3rd Annual Black Tie Charity Gala “Heaven” on January 16, 2010 in Beverly Hills, California.Getty

Westwick andJessica 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 theChicks in the Officepodcast 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 daughterBowie Ella Richardsonin January 2021 with former Vancouver Canucks player Brad Richardson, whom she married in August 2024.

Westwicktied the knotwith his wife,Amy Jackson, that same month after dating for three years.

04of 05Taylor Momsen and Chace CrawfordTaylor Momsen and Chace Crawford attend the Dolce & Gabbana and The Cinema Society Celebration for Madonna and the cast of “Filth and Wisdom” at The Thompson Hotel on October 13, 2008 in New York City.GettyIn the first season ofGossip 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, perPage Six.“It’s great, because going to set we’re all such good friends. And you know, rumors are rumors,” Momsen toldOK!in March 2009 after shutting down the possibility that she was dating Crawford.In June 2024, Crawford confirmed during an appearance onCall Her Daddythat 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.”

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Taylor Momsen and Chace Crawford

Taylor Momsen and Chace Crawford attend the Dolce & Gabbana and The Cinema Society Celebration for Madonna and the cast of “Filth and Wisdom” at The Thompson Hotel on October 13, 2008 in New York City.Getty

In the first season ofGossip 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, perPage Six.

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

In June 2024, Crawford confirmed during an appearance onCall Her Daddythat 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.”

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Kelly Rutherford and Matthew Settle

As another couple that had a romantic storyline throughout the six seasons ofGossip Girl,Kelly Rutherfordand 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 herkissing him on the cheekand herleaning 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.

source: people.com