Who: Teen Choice Award-winning actress Leighton Meester, 34, and Teen Choice Award-nominated actor Sebastian Stan, 38.
How They Met: The actor pair presumably met in 2007 when they both first appeared on The CW's hit drama Gossip Girl — Meester as series regular Blair Waldorf and Stan as recurring guest star Carter Baizen.
Rumors of an off-set romance began to swirl in early 2008 when Page Six reported that the two "couldn't keep their hands off of each other" during an industry dinner.
Mere months later, false reports of an engagement circulated, allegedly stemming from posts on the actors' Facebook pages.
In 2009, Stan called Meester "the most interesting, sophisticated, talented and an extremely funny person that I know."
Why We Loved Them: This was the era of Gossip Girl — and, more specifically, the era of Gossip Girl stars dating each other. Before their collective crash and burn, Blake Lively and Penn Badgley as well as Ed Westwick and Jessica Szohr were coupled up in real life.
And, I mean, why wouldn't 2008's coolest 20-somethings get together? It's convenient; it's good publicity; it gives you a reason to break out your largest alligator clutch and coolest graphic tee.
Plus, they were sweet. Stan told People he was "a really lucky guy" in regard to his relationship with Meester. When asked how he dealt with his girlfriend's kissing scenes on the show, he said, "It's work and everyone shares the same mentality when it comes to that. But we all laugh about it," adding, "The good part is I get to go home with her."
Stan reportedly bought Meester a (custom) painting for Valentine's Day in 2009. "He told the artist about me, my favorite colors and poetry and she painted a large very special abstract work I have hanging in my dining room," Meester said.
When They Peaked: Though somewhat private when it came to discussing their relationship, Meester and Stan weren't exactly camera shy. In the spring of 2009, the couple went to a basketball game with fellow Gossip Girl co-star Chace Crawford — and, like, made out at a basketball game in front of fellow Gossip Girl co-star Chace Crawford.
I guess Chace didn't seem to mind?
The Breakup: In spring 2010, about a year following their iconic courtside PDA, Meester and Stan were first reported to have broken up. At the time, OK! reported that Meester had called things off because she "doesn't know how to be in a relationship and doesn't really like them."
As bizarre as that reasoning might sound, Meester said as much herself toward the end of 2010, telling Seventeen that she'd "never really liked anybody before," and that in relationships "it was always a relief when we broke up."
In fact, she told British Glamour "I've hated every boyfriend I've had," while she and Stan were still together.
In that same Seventeen interview she reportedly admitted that her and Stan's breakup was the only experience "where it was really hard and I was really sad when it ended." Still, she found the positive in the situation, explaining that the split "taught me a lot about myself and love and life."
In 2014, Meester released her debut album Heartstrings. Meester said the title track, which includes verses like "You took me for granted all the time" and "Had to save my own self from all your evil games," was written about "some stupid breakup that I had when I was 25 or earlier."
"At the time it was like,' Screw you, I don't care about you anymore, and it's not going to happen!'" she continued. "Joker."
Given that Meester and Stan broke up when she was about 24, there's been speculation that the Marvel star is the "joker" in question. Meester has neither confirmed nor denied this theory.
Where They Are Now:
Meester wed fellow teen drama star Adam Brody in 2014. She and the O.C. alum welcomed daughter Arlo in 2015 and a son in late 2020.
The actress was most recently seen in ABC sitcom Single Parents, which was canceled shortly after its second season finale aired last May.
Stan is reportedly dating Spanish actress Alejandra Onieva.
Next up for the actor is Disney+ Marvel series The Falcon and the Winter Soldier, which premieres March 19. Stan has several other projects on the horizon as well, including Pamela Anderson and Tommy Lee miniseries Pam & Tommy — he's expected to play Lee opposite Lily James's Pamela.
#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.
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