This may not be the Upper East Side, but it's one reunion you don't want to miss.
The clip showed the You star—wearing a blue t-shirt with his hair down—taking a page from his on-camera sister's style book with the dark eyeliner, while Taylor herself brought the rock and roll attitude of Jenny, with a black and grey checkered flannel and ripped jeans.
Penn wrote on the Sept. 1 TikTok, "Next week on Podcrushed."
And fans flocked to the comments to voice their excitement, with one user exclaiming, "OMGGGG GOSSIP GIRL REUNION CRUMBS," while another wrote, "No way!!!!"
But this isn't the first moment fans of the CW show had to gossip about. Back in April, Taylor returned to the famous steps of New York City's Metropolitan Museum of Art after a decade.
Capturing Jenny's edgy style, the "Pretty Reckless" singer posed on the steps in baggy jeans, a black t-shirt and converse with her hair in pigtails, captioning the Instagram moment, "This picture feels familiar…"
Penn, too, has embraced the Gossip Girl nostalgia by having former co-stars on his podcast: Leighton Meester (who played Blair Waldorf) was on the debut episode of Podcrushed in 2022, followed by Chace Crawford, who portrayed Nate Archibald, in July 2022.
But speaking of Manhattan's most elite, Penn has been vocal about how ready he was to leave the gossip behind him when the series came to an end after six seasons in 2012.
"I didn't want to be in television," he told Vanity Fair in Feb. 2023. "I was biding time a lot with Dan—I was not invested. And I'm not saying it's a good thing! I'm saying it's just what it was."