Former Playboy model Zoe Gregory recently claimed that she had a fling with Justin Timberlake while he was dating Cameron Diaz in the early 2000s. Gregory stated that she met Timberlake at a party at the Playboy Mansion and made the first move on him. Despite Timberlake initially declining due to his relationship with Diaz, Gregory alleged that he eventually gave in to her advances. The encounter reportedly involved fooling around but not having sex.
Gregory had previously made headlines for alleging that Alex Rodriguez had sexted her just weeks before proposing to Jennifer Lopez. She described Rodriguez as being inappropriate and unfaithful in his interactions with her.
In a separate incident, Britney Spears accused Timberlake of cheating on her multiple times during their relationship. Spears claimed in her memoir that Timberlake had been unfaithful with another celebrity. There were also reports of Timberlake cheating with Nicole Appleton while still dating Spears.
Timberlake's dating history has been marred by rumors of infidelity. Following his split from Diaz, he was seen getting close to Jessica Biel at a party, which reportedly upset Diaz. Timberlake and Biel eventually married but faced rumors of Timberlake cheating with Olivia Munn.
In 2019, Timberlake was photographed holding hands with his co-star Alisha Wainwright, leading to speculation about their relationship. Timberlake later issued an apology, attributing his behavior to excessive drinking.
