Celebrity Celebrity Relationships Sebastian Stan Hints Gossip Girl Costar Leighton Meester Was His First 'Serious Love': 'Life Seemed Simpler' Stan and Meester dated from 2008 to 2010 after meeting on the set of 'Gossip Girl' By Stephanie Wenger Stephanie Wenger Stephanie Wenger is a TV Writer/Reporter at PEOPLE. She joined the brand in 2021 as a digital news writer, covering stories spanning across the site's verticals. She previously contributed E! Online, Hollywood Life and Oscar.com. People Editorial Guidelines Published on September 19, 2024 05:43PM EDT Sebastian Stan and Leighton Meester . Photo: Getty(2) Sebastian Stan is looking back at his first time falling in love. The 42-year-old actor opened up to Variety about his first serious relationship while reflecting on his time on the hit TV show, Gossip Girl. “It was the first time I was in serious love with somebody,” he shared of experience filming the CW series in New York City. “Walking around the city, seeing these same buildings and streets — life seemed simpler.” Sebastian Stan and Leighton Meester attend CALVIN KLEIN COLLECTION Hosts PARSONS Fashion Benefit 2009 Pre-Party at Calvin Klein Collection on April 2, 2009 in New York City. PATRICK MCMULLAN/Patrick McMullan Sebastian Stan's Dating History: From Leighton Meester to Annabelle Wallis Though he doesn't directly name his Gossip Girl costar and ex-girlfriend Leighton Meester, the two dated from 2008 to 2010. Stan — who played Carter Baizen on Gossip Girl — appeared in 11 episodes from 2007-2010. He's avoided publicly discussing his relationships over the years, but he spoke highly about Meester during their time together. "She's the most interesting, sophisticated, talented and an extremely funny person that I know. She's really hilarious," he told reporters about Meester in 2009. The pair called it quits the following year and Meester, 38, opened up about the break up in an interview with Seventeen. "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 shared about her relationship with Stan. Meet the Gossip Girl Cast's Real-Life Partners Since then, Stan has been linked to several of his co-stars, including Jennifer Morrison and Margarita Levieva, as well as Dianna Agron and the Spanish actress Alejandra Onieva. Most recently, the A Different Man star spent time with Malignant actress Annabelle Wallis. They were photographed holding hands in 2022. As for Meester, she has been married to husband Adam Brody since 2014. They share 7-year-daughter Arlo Day and a son who was born in 2020. Adam Brody and Leighton Meester arrive at Warner Bros. Pictures and New Line Cinema's world premiere of "SHAZAM!" on March 28, 2019 in Hollywood, California. Morgan Lieberman/FilmMagic Never miss a story — sign up for PEOPLE's free daily newsletter to stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories. Telling E! News about her “normal relationship with all the good and the hard" in 2023, Meester added that "we just make it work.” She continued, "We're super, super lucky, and I think we recognize how lucky we are with one another. We give each other a lot of respect and time and attention and focus. Like, really put our time and energy into a relationship." Close