Hey, there Upper East Siders, Gossip Girl here and I have the biggest news ever! It turns out that the personal lives of the actors and actresses are just as scandalous as they were on screen, because many of them actually dated one another in real life, including—gasp—Chuck and Vanessa?! Don’t believe me? Then, keep reading because, thankfully, we have gathered up pictures and quotes on all of the Gossip Girl real-life couples, and trust us when we say they’re just as dramatic as we thought.
Blake Lively (Serena van der Woodsen)
Blake Lively has been very famously married to Ryan Reynolds since 2012, but before that, she actually dated her Gossip Girl co-star, Penn Badgley.
The two dated for three years while filming the show, but split in 2010 to help try and balance their personal and professional lives.
In recent years, Badgley has opened up about how Lively helped him avoid addiction, saying “To be honest, I never struggled with substance. Blake didn’t drink, and I think our relationship in some ways saved me from forcing myself to go down that road.”
After Badgley, Lively met Ryan Reynolds on the set of Green Lantern. They began dating in 2011, got married in 2012 and now have four children together.
The couple often makes fun of one another online, walk red carpets together and go to dinner with their best friend, Taylor Swift—who is the godmother to three of their children.
Leighton Meester (Blair Waldorf)
Another person who dated their Gossip Girl co-star is none other than Blair Waldorf herself. From 2008 until 2010, Leighton Meester dated Sebastian Stan, who played Carter Bazien on the show—and went on to play the Winter Soldier in the Marvel Cinematic Universe.
“She’s the most interesting, sophisticated, talented and extremely funny person that I know,” Stan told reporters in 2009. “She’s really hilarious.”
The reason for the pair’s split remains unknown, but Meester did say “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.” This was in reference to their breakup.
Four years after that, Meester married Adam Brody after meeting on the set of The Oranges in 2011.
“He’s my best friend,” the actress said in 2019. “I wanna work with him on everything, and I think he’s the best in everything.”
Meester and Brody have since welcomed two children and are often seen walking red carpets together.
Ed Westwick (Chuck Bass)
Sadly, Chuck and Blair didn’t end up together in real life, but you know who almost did? Chuck and Vanessa! That’s right, Ed Westwick and Jessica Szohr dated in 2008, with the actress revealing, “A lot of us did date and I remember when Ed and I started dating, we wanted to keep it super private.”
“A couple of months in—we had been together for quite a bit before it came out—we were going to go to a New York Knicks game, and we went back and forth,” she continued. “Either we are going to live this private life and never leave our apartment, or we do it, and we just keep our s**t as private as we can. And we were people who liked going to sporting events and concerts and plays and stuff. After a couple of months, it got old. We need[ed] to leave.”
The relationship lasted two years before the couple decided to split. The reason remains unknown.
After that, Westwick kept a relatively low profile, especially given his multiple sexual assault charges in 2017. The allegations were since dropped, and the actor celebrated by marrying Amy Jackson in 2024.
“For me, [marrying Ed] means having a life partner to adventure with, to share love and support, to create a beautiful family and to have each other’s backs throughout all of life’s moments,” Jackson said. “It’s about building a future together and creating endless memories, knowing that we are a team through it all.”
As of this posting date, the couple doesn’t have any children.
Penn Badgley (Dan Humphrey)
After ending things with Lively, Badgley began dating Domino Kirke in 2014 and married her in 2017. They then welcomed their first child in 2020.
“Penn and I met at a meatball shop,” Kirke revealed on her husband’s podcast, Podcrushed. “I had never seen Gossip Girl, so I had no context for Penn.”
She then shared how at the time Badgley was couch surfing, so she offered him her spare bedroom.
“I got his number because I was really interested in him living with me, and I thought he was cute,” Kirke said.
Nowadays, the two often talk about each other on social media and in various interviews.
Jessica Szohr (Vanessa Abrams)
After leaving the Upper East Side and Westwick behind, Szhor remained single for a long time. Then, in August 2024, she married former hockey player Brad Richardson.
“It was the most magical, beautiful day, filled with the people we love the most,” Szhor said.
Both Szhor and Richardson have children from previous relationships, and it remains unclear if they plan to have any more.
Kelly Rutherford (Lily van der Woodsen)
Like her character, Lily van der Woodsen, Kelly Rutherford has been married multiple times. First to Carlos Tarahano from 2001 to 2002 and then to Daniel Giersch from 2006 to 2010, with whom she shares two children.
The custody battle for the children was quite difficult, though, because the judge granted both of them equal custody. However, since Giersch’s work visa has been revoked, the judge decided that the kids will live with him full-time in Monaco, meaning Rutherford either has to move there or just visit her kids when she is able.
“Yes, it was a challenging time. It was a heartbreaking time. But I focus on the good most of the time, I really do,” Rutheford said in 2024. “I’m very thankful for where we are. I have a great relationship with my kids.”
“They’re teenagers now, and they’ve got their friends and their stuff. So my day-to-day has recently been more about me and my dogs, working and traveling.”
It is unclear at this time how often Rutherford sees her kids. She attended Westwick’s—who played her adopted son on the show—wedding, though, and even gave a speech.
Matthew Settle (Rufus Humphrey)
Matthew Settle was married once in 2006 until 2011 to Naama Nativ Settle. They also have one child together.
“Things happen in life, and you just have to roll with it. I wish things could have been better, but our focus is on our daughter,” Settle said at the time of the split.
Since then, Settle hasn’t been in a public relationship and is hardly seen with his child.
