Penn Badgley Admits This Was Dan Humphrey's "Worst" Moment on Gossip Girl

Dan Humphrey had many cringeworthy moments during the original run of Gossip Girl, but what does Penn Badgley think is the worst thing his character ever did? See the answer for yourself.

By Kisha Forde Oct 21, 2021 8:18 PMTags
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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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And as for how he was able to make the switch from sneaky blogger to serial killer with his latest role as Joe in Netflix's You?

Penn said that although his new dangerous character is something he "thinks and worries" about, he noted his "acting is more of a spiritual thing."
 
"I'm just present with the words I read on the screen and when it's awful and it kind of like, makes your skin crawl, that's what comes up and that's what I do," he shared with Esquire. "I think if I tried to profile [Joe] really—like a psychopath—You would be disgusting and unwatchable."

Also, find out what his Wikipedia page was changed to at one point in time in the video above!

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