When a Former Playboy Model Claimed Justin Timberlake Cheated on Cameron Diaz With Her

Before dating and marrying Jessica Biel, Justin Timberlake was in a highly publicized relationship with Cameron Diaz. As per reports, Zoe Gregory, a former Playboy model, once claimed recently that she had an affair with Timberlake, while he was dating Diaz. Gregory told the Daily Mail that because of his relationship with Diaz, Timberlake originally turned down her advances when they first met at a party in the early aughts. The Playboy model then offered him an explanation, saying that Diaz was 'not with you now.'

At that point, Timberlake is said to have dived into the notorious grotto pool while just wearing his boxers. Gregory further added, "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. I didn’t have sex with him, but we had a fondle and we made out." However, reps for Timberlake or Diaz never commented on this incident. 

But this is not the only time such accusations have been hurled against the Rock Your Body singer. Moreover, Britney Spears claimed in her biography The Woman in Me that he cheated on her with 'another celebrity,' who was thought to be All Saints girl group member Nicole Appleton, and Timberlake can't seem to shake the persistent infidelity accusations since then.

In her memoir, Spears stated that she had an abortion when she was dating Timberlake. As per the BBC, she wrote, "I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated. But Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young. I’m sure people will hate me for this, but I agreed not to have the baby. I don’t know if that was the right decision. If it had been left up to me alone, I never would have done it. And yet Justin was so sure that he didn’t want to be a father."

Similarly, in 2019, Timberlake caused further controversy when he was seen on a New Orleans balcony holding hands with Palmer co-star Alisha Wainwright. After their 2012 wedding, the musician later apologized to his wife Biel. Timberlake wrote on Instagram, "A few weeks ago, I displayed a strong lapse of 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. This is not the example I want to set for my son [Silas]," as per CNN. The Grammy winner, who has a son Phineas, 3, and a daughter Silas, 8, with Biel, went on to "apologize to my amazing wife and family for putting them through such an embarrassing situation” and noted that he was “focused on being the best husband and father I can be." Though rumors circulated that Timberlake's interaction with Wainwright indicated marital issues, the couple has remained close.

Editor's Note: This article was originally published on Feb. 21, 2024. It has since been updated.