Justin Timberlake allegedly cheated on Cameron Diaz with Playboy model. A former Playboy model, Zoe Gregory brings allegations against Timberlake that he hooked up with her at the time when the SexyBack singer was dating actress Cameron Diaz. The blond bombshell told the Daily Mail that she met Timberlake met at a party at the Playboy Mansion, and it was not him but her only, who made the move first. Gregory claimed Timberlake initially declined, stating he was dating Diaz, but when she further teased him by saying that Diaz was “not with [him] now,” he allegedly gave in.
Justin Timberlake reportedly cheated on Cameron Diaz with Playboy model
Gregory elaborated on their encounter, stating that while they did not have sex, they “had a fondle and we made out.” She further recounted, “He [Justin Timberlake] 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.”
Timberlake and Diaz were in a relationship from 2003 to 2006 and reunited professionally in 2011 for their comedy-drama film, Bad Teacher. Reflecting on their collaboration, Diaz told Us Weekly, “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.”
Discussing the dynamic of working with an ex, Diaz added, “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.”
Britney Spears also claimed that he cheated on her
However, Gregory is not the first to accuse Cry Me a River singer Justin Timberlake of being unfaithful in an affair. Britney Spears also stated in her 2023 biography that she was cheated on by Timberlake “a couple of times” during their relationship.
Spears, who dated Timberlake from 1999 to 2002, described an incident in her recently published best-selling memoir in which the SexyBack singer allegedly boasted to one of her dancers about a female he had hooked up with the night before in Las Vegas. Timberlake allegedly told the dancer he “hit that last night,” according to her.
