Justin Timberlake's romantic entanglements have been a rollercoaster of heartbreak.
The latest bombshell comes from former Playboy model Zoe Gregory, who alleges that she had a fling with Timberlake while he was still dating Cameron Diaz. According to Gregory, their rendezvous happened at a party in the famed Playboy mansion. She claims to have made the first move on Timberlake, who initially resisted, citing his relationship with Diaz.
However, Gregory's persistence allegedly led Timberlake to succumb to temptation, fearing he'd appear weak. While they didn't engage in intercourse, Gregory asserts that they engaged in activities. Despite attempts to reach out for comment, representatives for Timberlake and Diaz remained silent.
This isn't Gregory's first time revealing affairs of the heart involving high-profile figures. In 2019, she made headlines by alleging an affair with Alex Rodriguez shortly before his proposal to Jennifer Lopez. Describing Rodriguez as "needy" and "horny," Gregory expressed her disapproval, deeming it unfair to Lopez.
Timberlake himself has faced accusations of infidelity. Britney Spears, in her 2023 memoir, accused him of cheating multiple times during their relationship. One notable incident involved Nicole Appleton of All Saints, sparking rumors of Timberlake's unfaithfulness while still with Spears. Reports also surfaced of Spears finding another woman, Tanya Mitchell, in Timberlake's bed, leading to a tumultuous breakup.
Timberlake's romantic escapades continued post-breakup with Diaz. In 2007, he was spotted cozying up to Jessica Biel, causing speculation and tension. Despite rumors of infidelity, Timberlake denied allegations of cheating with Olivia Munn while dating Biel. Yet, whispers persisted, hinting at a passionate encounter at a Park Avenue hotel. Ultimately, Timberlake and Biel tied the knot in 2012, weathering storms and welcoming children together.
However, Timberlake's fidelity came into question once more in 2019 when he was photographed holding hands with co-star Alicia Wainwright. Amid public scrutiny, Timberlake issued a public apology, attributing his behavior to excessive drinking. Despite the reassurances, the incident reignited doubts about Timberlake's commitment and integrity in relationships.
