Penn Badgley Reveals Dan Humphrey’s Worst Moment on Gossip Girl

We can pump the brakes on the XOXOs when it comes to one major moment that happened between the OG Gossip Girl and Dan Humphrey’s little sister, Jenny.
 
Penn Badgley, who played Dan Humphrey and—BIG spoiler alert—the mysterious titular character herself in the series’ original run, recently revealed his pick for Dan’s “worst” moment on Gossip Girl.
 
While reflecting on his, um, villainous character, in an Oct. 19 video for Esquire, the actor revealed Dan crossed a line when he publicly outed the moment his little sister, Jenny (played by Taylor Momsen) lost her virginity to the entire world of Upper East Siders.
 
“He’s the worst, but what’s the actual worst thing he did? Okay,” Penn answered in the Explain This segment. “Didn’t he—he outed his sister losing her virginity. These storylines are twisted.”

Yes, you read that right (and may even remember it). Just a refresher since it’s been almost 10 years since the series ended in 2012: Dan Humphrey, masked as the anonymous gossip blogger otherwise known as Gossip Girl, leaked that very private piece of information to all of her high school peers, humiliating her.

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