In a revelation that has sent shockwaves through the entertainment industry, former Playboy model Zoe Gregory has come forward with claims that Justin Timberlake, once celebrated as America's heartthrob, engaged in a romantic encounter with her while he was in a relationship with actress Cameron Diaz. Gregory's allegations have reignited discussions about Timberlake's past relationships and his reputation in the public eye.

According to Gregory, the incident took place at the iconic Playboy Mansion, where she initiated an advance towards the then-NSYNC member. Despite Timberlake's initial hesitation, Gregory alleges that the singer succumbed to temptation when assured of Diaz's absence. "He didn't want to look like a wimp," Gregory recounted to The Daily Mail, describing how their encounter escalated within the mansion's famed grotto, though she clarifies that it did not culminate in sexual intercourse.

This bombshell claim has not yet elicited responses from Timberlake or Diaz's representatives, leaving the public to speculate on the veracity and implications of Gregory's account. The narrative is further complicated by Gregory's additional revelation of a liaison with baseball star Alex Rodriguez, shortly before his engagement to Jennifer Lopez, describing him as "being like a dirty dog."

The resurgence of interest in Timberlake's romantic history follows a period of intense scrutiny triggered by Britney Spears' revelations about their relationship in the early 2000s. Spears, in her memoir "The Woman In Me," disclosed a deeply personal and painful decision to terminate a pregnancy resulting from their relationship, a decision influenced by Timberlake's expressed unreadiness for fatherhood.

The public fallout between Spears and Timberlake has been marked by a series of accusations and threats of legal action, particularly after Timberlake's defiant refusal to apologize at one of his concerts, which Spears countered with a threat to sue.

These developments paint a complex portrait of Timberlake, challenging the clean-cut image he once enjoyed and prompting a reevaluation of his legacy in the music and entertainment industry. As the story unfolds, fans and observers are left to grapple with the juxtaposition of Timberlake's musical achievements and the emerging narratives that suggest a more turbulent personal life.