Playboy Model Claims Justin Timberlake Cheated on Cameron Diaz

Former Playboy model Zoe Gregory is claiming that she hooked up with Justin Timberlake while he was dating Cameron Diaz.

Gregory, now 49, told the Daily Mail on Sunday, February 18, that Timberlake, now 43, initially refused her advances when they met at a party in the early aughts due to his relationship with Diaz, now 51.

However, Gregory claimed that after she teased Timberlake that Diaz was “not with [him] now,” the pair allegedly hooked up in Hugh Hefner’s indoor pool at the Playboy Mansion in Los Angeles.

“He didn’t want to look like a wimp. We both got in the grotto, and we both got our kit off — down to his shorts — and we ended up fooling around,” Gregory claimed. “I didn’t have sex with him, but we had a fondle and we made out.”

Us Weekly has reached out to Timberlake for comment.

Timblerlake and Diaz dated from 2003 to 2006 before reuniting onscreen in the 2011 film Bad Teacher.

“Justin and I have always had a good laugh together, and to make a movie where we get to have a laugh together, and there really was no one else who was more perfect for this part,” Diaz exclusively told Us of the project in March 2011. “It really wasn’t a big deal, we had a great time and did the job, and we do what all actors do afterward: We all go our separate ways.”

Gregory’s claim about Timberlake and Diaz is not the first time Timberlake has come under fire for alleged infidelity. In her 2023 memoir, The Woman In Me, Britney Spears claimed that Timberlake cheated on her “a couple of times” throughout their relationship.

Spears, 42, who dated Timberlake from 1999 to 2002, recalled one instance when the “SexyBack” singer allegedly bragged to one of her dancers about a girl he hooked up with the night before in Las Vegas. She claimed that Timberlake told the dancer he “hit that last night.”

Timberlake also sparked controversy in 2019 when he was photographed holding hands with Palmer costar Alisha Wainwright on a balcony in New Orleans. The musician subsequently issued an apology to wife Jessica Biel, whom he wed in 2012.

“A few weeks ago, I displayed a strong lapse of judgment — but let me be clear — nothing happened between me and my costar,” Timberlake wrote via Instagram at the time. “I drank way too much that night and I regret my behavior. I should have known better. This is not the example I want to set for my son [Silas].”

The Grammy winner, who shares Silas, now 8, and son Phineas, 3, with Biel, 41, went on to “apologize to my amazing wife and family for putting them through such an embarrassing situation” and noted that he was “focused on being the best husband and father I can be.”

Despite speculation that the moment with Wainwright, 34, suggested problems in his marriage, Timberlake and Biel have maintained a strong bond.

“I sometimes feel like 10 years has just flown by in the blink of an eye and other times I feel like, ‘Oh, my gosh, 10 years, that’s a really substantial amount of someone’s life,'” Biel told Access Hollywood in April 2022, months before the duo celebrated 10 years of marriage. “I just feel really proud of it. … We’ve had our ups and downs like everybody and I’m just really proud of it, and I’m still the happiest and loving my life.”