Former Playboy model Zoe Gregory claims she once hooked up with Justin Timberlake while the “SexyBack” crooner was dating Cameron Diaz in the early aughts.
The blond bombshell, now 49, told the Daily Mail on Sunday that she met Timberlake, now 43, at a party at the Playboy Mansion, and she was first to make a move on him.
Gregory claimed the “Rock Your Body” singer initially declined, stating he was dating Diaz, but when she further enticed him by saying the “Charlie’s Angels” star was “not with [him] now,” he allegedly gave in.
Former Playboy model Zoe Gregory claims she hooked up with Justin Timberlake while he was dating Cameron Diaz.Zoe Gregory/Instagram
Timberlake dated Diaz from 2003 to 2007.Getty Images“He didn’t want to look like a wimp,” she told the outlet. “We both got in the grotto, and we both got our kit off — down to his shorts — and we ended up fooling around.”
The porn star clarified she and Timberlake did “not have sex,” but they allegedly fondled and “made out.”
Page Six has reached out to his reps for comment but did not immediately hear back. Diaz’s reps also did not respond.
“We both got in the grotto … we ended up fooling around,” Gregory alleged.Zoe Gregory/Instagram
Gregory claimed Timberlake acknowledged he was dating Diaz, but then gave in to the model’s advances.Getty ImagesGregory previously exposed another taken man with whom she allegedly had a tryst: Alex Rodriguez.
In 2019, she claimed A-Rod had sexted her just weeks before he proposed to Jennifer Lopez.
“He was being like a dirty dog. He seemed like a needy, horny bloke,” Gregory told the Sun at the time. “If he is doing this right up until the point he is proposing to her, it is just not fair.”
Gregory, seen here with Hugh Hefner, moved into the Playboy Mansion in 2001.AFP via Getty Images
She previously alleged to also having had a tryst with Alex Rodriguez.WireImageTimberlake’s dating record has not been squeaky clean either.
Britney Spears recently accused the “Cry Me a River” singer of cheating on her multiple times throughout their three-year relationship.
The Princess of Pop, 42, claimed in her bestselling memoir “The Woman in Me,” released in October 2023, that Timberlake had been unfaithful to her with “another celebrity.”
The former *NSYNC member was rumored to have cheated with Nicole Appleton of the English girl group All Saints after they were spotted heading back to his hotel in London in 2000 — while he was still with Spears.
Britney Spears accused Justin Timberlake of cheating on her more than once.Ron Galella Collection via Getty ImagesIt was also reported amid the pop icons’ romance that the “Oops! …I Did It Again” singer once flew into a “jealous rage” when she found Tonya Mitchell, an up-and-coming singer who had performed as one of *NSYNC’s opening acts, on her then-boyfriend’s bed, according to an archived Star magazine article.
Timberlake then broke up with Spears via text when he found out she cheated on him with choreographer Wade Robson.
Despite his own heartbreak, the “What Goes Around … Comes Around” singer has since been caught in more compromising situations.
Timberlake has not admitted to his alleged indiscretions.Getty ImagesJust a few weeks after his split from Diaz, now 51, in 2007, Timberlake was seen chatting up Jessica Biel at a Golden Globes party, which reportedly infuriated the “There’s Something About Mary” star. It’s unclear whether there was any crossover between those two relationships.
The “Selfish” singer dated the “7th Heaven” alum for some time, but in 2010 he was rumored to have cheated on her with Olivia Munn. He denied the allegations at the time via his rep.
Sources claimed the “Daily Show” alum, now 43, resisted his advances initially, but then gave in to a night of passion at her Park Avenue hotel, where the pair were “openly affectionate.”
Timberlake and Biel, 41, overcame that hurdle, going on to wed in 2012 and have two kids together.
Timberlake allegedly cheated on Jessica Biel early on in their relationship.Getty Images
The pop star was later caught holding hands with his movie co-star in 2019.Getty ImagesHowever, in November 2019, the former boy band member was caught holding hands with his then-co-star Alisha Wainwright off-set while they were filming a movie in New Orleans.
Timberlake issued an apology shortly after, writing via Instagram in part, “A few weeks ago I displayed a strong lapse in judgement [sic] — 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.”
