Hilary Duff Knows How Iconic Her Gossip Girl Threesome Is

Every former Disney star needs their “Can’t Be Tamed” moment — that scintillating, rebellious scandal which announces to the world they’re no longer a squeaky-clean kids show actor. For Hilary Duff, that arrived in 2009, when the Lizzie McGuire star embraced her sexuality on Gossip Girl. Though her guest starring stint as the famous actor Olivia Burke was short, it was hugely memorable because of one sizzling scene.

Duff poked a bit of fun at herself during Season 3 of Gossip Girl by playing a movie star who can’t seem to escape the spotlight even if she’s just trying to live a normal life by enrolling in NYU. Olivia had a fling with Dan Humphrey, which quickly evolved into a bit of experimentation. To get the full college experience, Olivia insisted that on having a threesome, inviting Dan and his bestie Vanessa to hook up with her.

When Harper’s Bazaar recently asked what Duff’s most memorable moment from filming the series was, she obviously pointed to this boundary-pushing sex scene. "Probably the threesome was the most standout moment," Duff said, adding that she was concerned how her mother would handle is: "Oh, my mom's going to call me after this one."

Duff’s worries at the time make total sense. The threesome scene had become an incredibly hot button issue even before it aired in late 2009. Family groups began loudly protesting the show when the threesome was first teased, and for Duff personally, it marked a boldly new direction in her otherwise PG acting career up to that point.

Clearly, the risk paid off — Olivia, Dan, and Vanessa’s threesome remains one of the buzziest moments to come from Gossip Girl. And fans are still obsessed with Duff’s character, as she revealed later in her Harper’s Bazaar interview.

"I was in Paris not too long ago and my bag got lost. I went up to the lady who worked at the airline and she's like, 'Are you on Gossip Girl?'" Duff said. "'Yes. Love that's how you know me.'"