Before Justin Timberlake embarked on his journey with Jessica Biel, there was a notable chapter in his romantic history with Cameron Diaz. Their high-profile relationship, spanning from 2003 to 2007, captured headlines and public interest. However, persistent rumors of infidelity have trailed Timberlake over the years, resurfacing recently.
Allegations from Playboy Bunny Zoe Gregory, who resided in Hugh Hefner’s famed Playboy Mansion, have added fuel to the speculation. According to reports, Gregory claimed to have had an encounter with Timberlake while he was still involved with Diaz. Their paths crossed at a party hosted by Hefner, where Timberlake initially resisted Gregory’s advances due to his relationship status, told Daily Mail.
However, Gregory allegedly persuaded him otherwise, pointing out that Diaz was not currently with him. Subsequently, Timberlake purportedly engaged in a playful escapade with Gregory in the mansion’s grotto pool, an iconic location within the Playboy Mansion lore.
Gregory did not mince words when recounting the incident, stating they both shed their clothing, albeit Timberlake only down to his boxers and engaged in intimate behavior. While their interaction did not escalate to intercourse, Gregory claimed they indulged in physical affection. Despite Diaz having moved on and found happiness in her marriage to Benji Madden, revelations of past infidelity can undoubtedly stir uncomfortable emotions.
Timberlake’s history with relationship turbulence traces back to his earlier years, notably during his time with Britney Spears, who accused him of cheating with another celebrity, speculated to be Nicole Appleton of the All Saints girl group. Moreover, reports suggest Timberlake was unfaithful to Diaz with whom he was romantically involved, and later with Olivia Munn in 2010. The affair with Munn gained attention through headlines in Us Weekly, detailing allegations of Timberlake misleadingly indicating the end of his relationship with Biel while engaging in an affair with Munn.
Despite the challenges, Biel and Timberlake eventually tied the knot in 2012. However, their relationship continued to face public scrutiny. In November 2019, Timberlake was photographed holding hands with his Palmer co-star, Alisha Wainwright, during a night out. While sources close to the actor downplayed the incident as innocent, Timberlake publicly apologized for his behavior, acknowledging a lapse in judgment and expressing regret for the embarrassment caused to his wife and family.
