‘Gossip Girl’: Which Cast Members Dated Each Other?

Gossip Girl is a teen drama that originally ran from 2007 to 2012. It features many juicy story lines about sex, love, and heartbreak.

When the cameras weren’t rolling, some cast members had their own romance stories going on as well. In fact, quite a few cast members of Gossip Girl dated each other. 

Blake Lively and Penn Badgley kissing on the set of 'Gossip Girl'
Blake Lively and Penn Badgley on the set of ‘Gossip Girl’ | James Devaney/WireImage

Blake Lively and Penn Badgley

Blake Lively (Serena van der Woodsen) and Penn Badgley (Dan Humphrey) were a major couple on the show, and the actors apparently also had chemistry off the screen.

Lively and Badgley dated during the few early years of the show. When they broke up, they tried to hide it from the cast and crew as they did not want their personal life interfering with their work.

“The shocking thing was, I found out on the set of the season 2 finale that Blake and Penn had broken up months before,” executive producer Joshua Safran told Vanity Fair. “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.”

Leighton Meester and Sebastian Stan

Sebastian Stan and Leighton Meester playing with a toy together
Sebastian Stan and Leighton Meester | Astrid Stawiarz/Getty Images

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Leighton Meester (Blair Waldorf) and Sebastian Stan (Carter Baizen) were another on-screen romance that seeped into real life. 

According to The Things, Meester and Stan dated from around 2008 to 2010. They spoke about each other a few times to media outlets but otherwise kept their relationship private.

In 2014, Meester released a song called “Heartstrings,” which many fans believe is about Stan. The song talks about an ex who broke Meester’s heart, but she has never confirmed who the song is actually about.

Jessica Szohr and Ed Westwick

Jessica Szohr and Ed Westwick smiling
Jessica Szohr and Ed Westwick | Frazer Harrison/Getty Images

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Like Meester and Stan, Jessica Szohr (Vanessa Abrams) and Ed Westwick (Chuck Bass) also dated from around 2008 to 2010.

A source told Page Six that Szohr reportedly cheated on Westwick while he was filming in Europe. The insider alleged, “Jessica recently celebrated her birthday in LA and was being openly affectionate and flirty with [Westwick’s friend] Marco [Minuto]. They ended up back at the same hotel, but nobody knows what happened behind closed doors.”

Kelly Rutherford and Matthew Settle

Matthew Settle and Kelly Rutherford smiling
Matthew Settle and Kelly Rutherford | Michael Stewart/WireImage

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Kelly Rutherford (Lily van der Woodsen) and Matthew Settle (Rufus Humphrey) also had a relationship on the screen, and they were rumored to dating in real life as well. According to Buzzfeed, Rutherford and Settle posted numerous pictures of each other on their Instagram accounts.

However, neither actor has ever confirmed this rumor. Instead, they often talk about their close friendship. In 2010, Settled talked about this as they went through breakups with their previous relationships.

“We’re good friends,” Settle told People (per Entertainment Weekly). “Kelly and I have a lot in common because we are supporting each other at this time in our lives.”

In 2017—five years after Gossip Girl ended—Rutherford posted a sweet birthday message for Settle on Instagram. She wrote, “Happy Birthday to my handsome soulful friend @matthew_settle. I love you and think the world of you. As an actor, father and friend. Sending you so much love today and everyday.”