These two were late 2000s royalty.
Fun fact: Blair Waldorf and Carter Baizen — I mean, Leighton Meester and Sebastian Stan — dated from around 2008 to 2010 after meeting on the set of Gossip Girl.
When asked how he felt about Meester’s kissing scenes with Ed Westwick, who played Chuck Bass, he said, “It’s all work and everyone shares the same mentality when it comes to that. But we all laugh about it. The good part is I get to go home with her.” BRB, swooning.
For Valentine’s Day 2009, the couple reportedly went on a Jamaican vacation with Westwick and Jessica Szohr, who were also an item at the time. Meester told Buzznet Stan gifted her a painting she hung in her dining room. “He told the artist about me, my favorite colors and poetry and she painted a large very special abstract work.”
They broke up in April 2010, and although neither confirmed a reason for the split, a source claimed to OK! Meester reportedly ended it because she “doesn’t know how to be in a relationship and doesn’t really like them.” Prior to the breakup, in December 2009, Meester told British Glamour, “Honestly, I’ve hated every boyfriend I’ve had.”
However, it doesn’t seem like Stan was one of them. In December 2010, Meester referenced the breakup, telling 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.”