Justin Timberlake’s recent arrest in New York has reportedly served as a wake-up call for his wife, Jessica Biel, rekindling concerns about their tumultuous relationship history marked by infidelity allegations. According to sources close to the couple, Biel is at a crossroads and may issue an ultimatum to Timberlake: seek help or face the possibility of divorce.

In Touch Weekly reported that Biel felt deeply humiliated by Timberlake's arrest, which has intensified the scrutiny on their 17-year relationship. “Justin has humiliated her again,” an insider told the magazine. “This could all lead to a divorce bombshell. No one would be shocked if Jessica issued Justin an ultimatum: Get help—or it’s over.”

Friends of Biel reportedly believe she has endured enough, referring to Timberlake as a "loser" and expressing frustration over Biel’s continuous efforts to keep him on the straight and narrow. “The arrest was a wake-up call: It’s time for her to realize she can’t do it alone. If he keeps going down this path, their marriage will be over,” the source added.

Throughout their 17 years together, 12 of which they have been married, Biel has faced numerous allegations of Timberlake’s infidelity. The couple's relationship was first rocked in 2010 when Timberlake allegedly had a weekend fling with actress Olivia Munn in New York City, reportedly after telling Munn that he and Biel had already split. Although Timberlake and Biel briefly broke up in 2011, they reconciled and married in December 2012.

Despite their marriage, the infidelity rumors persisted. In late 2012, Timberlake was rumored to have made out with another woman on a couch just before his wedding. In 2013, he was alleged to have kissed actress Thaila Ayala in Brazil. A year later, in Paris, Timberlake was seen getting flirty with his backup singer, Zenya Bashford. “He was rubbing and caressing her from behind, dancing in a way that no married man should ever dance with someone who isn’t his wife,” a source detailed.

One of the more publicized incidents occurred in 2019 when Timberlake was photographed holding hands and getting cozy with his Palmer co-star Alisha Wainwright during a night out in New Orleans. Timberlake later apologized, stating, “I drank way too much that night, and I regret my behavior. I displayed a strong lapse of judgment.”

In an effort to shield Timberlake from further temptations, Biel had the family spend more time in Montana around that period. “They were trying to focus on their family and their marriage. At one point, I’d heard he was offered a big contract for a Vegas residency, and she thought it would be a horrible idea, so he turned it down. She knows how easy it is for him to get caught up in the partying and where that will lead. He doesn’t know how to turn it off,” the source explained.

The rumors did not stop there. In 2021, Timberlake was claimed to have made out with another woman in Atlanta. Furthermore, in 2024, Playboy cover girl Zoe Gregory revealed that Timberlake had cheated on her while he was dating Cameron Diaz in the 2000s. “He just can’t escape this ‘cheater’ label, and it upsets Jessica every time,” confirmed a source. “Her friends fear he’ll break her heart again: Do cheaters ever change?”