Justin Timberlake is facing another cheating scandal. Former Playboy model Zoe Gregory claims she hooked up with the singer while he was dating Cameron Diaz in the early aughts.

Zoe, 49, says Justin, 43, initially refused her advances when they met at a party due to his relationship with Cameron, 51, but after Zoe teased him that Cameron was “not with [him] now,” the pair allegedly hooked up in Hugh Hefner’s pool at the Playboy Mansion in L.A. “He didn’t want to look like a wimp. We both got in the grotto, and we ended up fooling around,” Zoe recalls.

“I didn’t have sex with him, but we had a fondle, and we made out.” News of the tryst “shook” Justin’s wife, Jessica Biel, 41, a source exclusively tells In Touch. “What wife wants to hear that her husband cheated in the past?” says the source. “Plus, it brings back bad memories for Jessica because [in 2019] Justin was accused of cheating on her after he was photographed holding hands with his Palmer co-star Alisha Wainwright while on location in New Orleans.”

More recently, Justin came under fire when Britney Spears claimed in her 2023 memoir, The Woman in Me, that Justin cheated on her “a couple of times” throughout their relationship. “It’s a lot for Jessica.”

Have a tip? Send it to us! Email In Touch at contact@intouchweekly.com.