Former Playboy model Zoe Gregory has made a sensational claim, alleging that she had an affair with Justin Timberlake while he was dating actress Cameron Diaz. Gregory revealed to the Daily Mail that she met Timberlake at a party in the early 2000s, where he initially declined her advances due to his relationship with Diaz. However, she reportedly convinced him by saying that Diaz was “not with you now.”
According to Gregory, Timberlake eventually joined her in the notorious grotto pool wearing just his boxers. “He didn’t want to look like a wimp,” she said, adding that they ended up fooling around. Although she clarified they didn’t have sex, they “made out and fondled.” Neither Timberlake nor Diaz’s representatives have commented on these allegations.
This isn’t the first time Timberlake has faced accusations of infidelity. Britney Spears, in her memoir The Woman in Me, alleged that Timberlake had cheated on her with another celebrity, rumored to be Nicole Appleton of All Saints. Spears also shared in her book that she had an abortion while dating Timberlake, saying, “Justin didn’t want to be a father” at the time, and she agreed to his wishes, though she had doubts about the decision.
Timberlake’s past controversies have continued to spark rumors. In 2019, he was spotted holding hands with his Palmer co-star Alisha Wainwright on a New Orleans balcony. Timberlake later apologized to his wife, Jessica Biel, via Instagram, acknowledging a “strong lapse of judgment.” He clarified that “nothing happened” between him and Wainwright but regretted his behavior, stating, “This is not the example I want to set for my son.”
Despite these controversies, Timberlake and Biel, who share two children, have remained together and continue to present a united front as a couple.
