Before Justin Timberlake dated and married Jessica Biel, he had a very high-profile romance with Cameron Diaz. The duo was together for four years from 2003 until 2007, but the rumors of infidelity have long haunted the “Cry Me a River” singer — and they have resurfaced again.
Playboy Bunny Zoe Gregory, who lived in Hugh Hefner’s Playboy Mansion, claimed to the Daily Mail that she had a fling with Timberlake while he was dating Diaz. They met at one of Hefner’s parties where the former NSYNC star initially resisted Gregory’s advances because he had a girlfriend. The Playboy star reportedly gave him an excuse since Diaz was “not with you now” and that’s when Timberlake allegedly stripped down to his boxers and jumped into the infamous grotto pool. 
Related story Justin Timberlake Is Seemingly Embracing His Scandals by Opening a Bar With This Highly-Controversial Star
Gregory was not shy nor discreet about what happened next. “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,’ she claimed. “I didn’t have sex with him, but we had a fondle and we made out.” While Diaz is now happily married to Benji Madden and probably doesn’t care about what happened in the past, it’s never a good feeling to be cheated on.
Timberlake can’t seem to escape the constant infidelity rumors since they began during his young relationship with Britney Spears, who alleged in her memoir, The Woman in Me, that he cheated on her with “another celebrity,” who was rumored to All Saints girl group member, Nicole Appleton. Besides Gregory, the 42-year-old singer reportedly cheated on Diaz with his now-wife… and then reportedly stepped out on his Biel relationship with Olivia Munn in 2010. (Are you following all of this?)
The Munn affair was an Us Weekly headline story where they alleged that he was telling the then-Daily Show correspondent that “it’s over with Jessica,” even though “the reality is he’s just doing it behind her back.” An insider claimed that Munn “had amazing sex” with Timberlake during a three-day affair in New York City. Biel and Timberlake were able to work things out and they walked down the aisle in 2012 — but their troubles were not behind them.
In November 2019, Timberlake was spotted holding hands on a drunken night out with his Palmer costar, Alisha Wainwright. While a People source close to the married actor said it was “completely innocent,” he did offer a public apology. “A few weeks ago I displayed a strong lapse in judgment — but let me be clear — nothing happened between me and my costar. I drank way too much that night and I regret my behavior. I should have known better,” he wrote while apologizing to his “amazing wife and family for putting them through such an embarrassing situation.” Related story Justin Timberlake Is Seemingly Embracing His Scandals by Opening a Bar With This Highly-Controversial Star
Before you go, click here to see all the celebrity couples who have stayed together after cheating scandals.
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