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Former Playboy Model Zoe Gregory Claims Justin Timberlake Cheated On Cameron Diaz With Her, Recalls Alleged Encounter At Playboy Mansion
According to Gregory, she shared a purported intimate encounter with Timberlake while he was still romantically involved with Cameron Diaz. Timberlake and Diaz dated between 2003 and 2006.
Former Playboy model Zoe Gregory has claimed that Justin Timberlake hooked up with her while he was still dating Cameron Diaz. Gregory, 49, told the Daily Mail on Sunday, February 18, that Timberlake refused her advances initially at a party at the Playboy Mansion in Los Angeles. However, after she teased the Selfish singer that her then-girlfriend Diaz was “not with [him] now,” the pair allegedly hooked up.
Justin Timberlake cheated on former girlfriend Cameron Diaz with a Playboy model?
Gregory further claimed that she “didn't have sex with him, but we had a fondle and we made out.” Earlier, in the same statement to the Daily Mail, the former Playboy model asserted, “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 dated between 2003 and 2006. The duo also later reunited in 2011 for their comedy-drama film Bad Teacher. Speaking to Us Weekly at the time, Diaz said, “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.” 
About the chemistry and camaraderie, while filming and spending time together as exes, Cameron 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.”
Gregory’s claim about Justin Timberlake, though, is not the first time the Cry Me a River singer has been accused of being unfaithful in a relationship. In her 2023 memoir, Britney Spears too claimed that Timberlake cheated on her a “couple of times” throughout their relationship.
Did Justin Timberlake cheat on Britney Spears? — The latter claims in her memoir
In her recently released best-selling memoir, Spears, who dated Timberlake from 1999 to 2002, recounted an incident where the SexyBack singer purportedly boasted to one of her dancers about a girl he had hooked up with the previous night in Las Vegas. She claimed that Timberlake told the dancer he “hit that last night.”
His other cheating scandals over the years
Timberlake also sparked controversy in November 2019 when he was photographed holding hands with his Palmer costar Alisha Wainwright on a balcony in New Orleans. The musician later issued a public apology to wife Jessica Biel, whom he married in 2012.
He wrote via Instagram, “A few weeks ago, I displayed a strong lapse of Judgement – but let me be clear – nothing happened between me and my costar.”
He continued, I stay away from gossip as much as I can, but for my family, I feel it is important to address recent rumours that are hurting the people I love. I drank way too much that night and regret my behavior. I should have known better. This is not the example I want to set for my son."
Timberlake further apologized to his "amazing wife and family for putting them through such an embarrassing situation" and affirmed that he is focused "on being the best husband and father I can be."
Timberlake and Biel have been married for more than a decade now and share two children, sons Silas and Phineas, who are 8 and 3 years old, respectively.
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