The Unavoidable Red Flags In Jessica Biel & Justin Timberlake's Marriage

Jessica Biel and Justin Timberlake have been Hollywood romance royalty ever since they were first spotted together in early 2007. They've gone on to welcome two sons, Silas and Phineas, and have celebrated huge milestones including their 10th wedding anniversary in 2022.

But, sadly, just like with Nick Jonas and Priyanka Chopra's relationship, the inevitable red flags came as thick and fast as the celebrations — including plenty of divorce speculation. In January, Biel shared interesting verbiage in her Instagram birthday tribute to her husband. "Another year growing and evolving and sometimes devolving, with you. Another year laughing about it all," she wrote, in part. But "devolving" raised eyebrows. "For her to make a dig like that in a birthday message is a clear sign things are not well between Jessica and Justin," a source told Radar Online. "Fans have gone wild speculating they are headed for the divorce court," they added. But rumors of trouble in paradise aren't the only potentially worrying facet of this relationship.

Justin Timberlake and Jessica Biel went their separate ways in March 2011 after around four years of dating, with their rep telling People, "They mutually have decided to part ways. The two remain friends and continue to hold the highest level of love and respect for each other." But they were back together and engaged by early 2012. We're giving your permission to get back with your ex, but it's rarely a green flag to break up before going the distance, as it implies incompatibility.

Exactly why they split wasn't made public, but if they didn't put in the work to resolve whatever issues they had, that would create the potential for trouble. "You need to identify the patterns in the previous relationship which didn't work before and then both be truly committed to working towards what is best for the relationship rather than just what is best for you," clinical psychologist and tantric sexuality coach Gemille Cribb explained to GQ Australia. "Old hurts need to be given a supportive listening ear by your partner and then you both must agree to not bring up the past and only focus on managing current issues," Cribb added.

Justin Timberlake shocked the world when The Sun published shots of him and his "Palmer" co-star Alisha Wainwright getting close while out with the movie's cast and crew in 2019. The snaps showed Wainright's hand on Timberlake's leg, and showed them holding hands.

Timberlake apologized in a since-deleted Instagram post. "I displayed a strong lapse in judgment — but let me be clear — nothing happened between me and my co-star. I drank way too much that night and I regret my behavior," he wrote (via People). "I apologize to my amazing wife and family for putting them through such an embarrassing situation, and I am focused on being the best husband and father I can be." A bigger red flag? A source told Us Weekly the apology was Biel's idea. "She felt embarrassed by his actions and wanted him to take accountability," they claimed. "Jessica was very upset and embarrassed by Justin's behavior."

The photos humiliated Biel, and while she had every right to remain married, it's imperative she stayed because she wanted to, not because she bought into the concept of 'The One.' "If we hold on to the idea that they are our soulmate, we could stay in a relationship that is unhealthy and possibly toxic. We wed ourselves to the idea of 'the one' instead of continuing to evaluate the quality of the relationship," licensed psychologist and relationship expert Dr. Kimber Shelton told Bustle.

Justin Timberlake's drama with Alisha Wainwright wasn't the first time he's been accused. In 2010, Us Weekly reported he'd supposedly been unfaithful with Olivia Munn. "[Timberlake] has been telling people it's over with Jessica, even though the reality is he's just doing it behind her back," a source claimed. His rep refuted the allegations, but speculation didn't go away. Biel and Timberlake continued their relationship, but Life & Style claimed he was still messaging Munn. "One [text message] said, 'My relationship is basically over.' The other said, 'I'm thinking about you.' There was part of a third that said something like, 'You don't understand how hard it is,'" a source purported (via HuffPost).

But that wasn't all. The following year, rumors swirled his split with Biel may have been because he'd cozied up to "Friends With Benefits" co-star Mila Kunis. A source denied the allegations to Daily Mail, hitting back, "Mila had nothing to do with their break-up. In fact, no one came between them." Neither cheating claim was confirmed, but it's bad if your partner is repeatedly being accused of inappropriate behavior.

To weather the storms, Biel needed to trust and forgive Timberlake implicitly, or walk away. As Kalley Hartman, LMFT at Ocean Recovery, exclusively told us when discussing how to trust when you're dating someone who has cheated before, "Staying with someone [you] don't trust or haven't forgiven will only build more distrust and resentment."

Justin Timberlake made headlines again in 2024 when he was arrested for DWI. Naturally, Jessica Biel wasn't happy about this, with a source telling People, "[He has] done everything he can [to make up] for the incident." The insider added Justin's behavior wasn't a dealbreaker for Biel, but noted, "They've been married for a long time. They have to work on their marriage like most couples. Being working parents is never easy." Another source told Us Weekly of the "7th Heaven" star's reaction, "Jessica is extremely upset. She was shocked to hear the news and had no idea as she was working. She was really worried about him."

Though they stayed together, it's a red flag if Biel can't trust her husband — she may feel resentment or embarrassment if he is constantly courting controversy. "It's taken a lot for Jessica to hang on through these ups and downs," a Radar Online source claimed, implying Biel's loyalty has been tested.

A separate source told Radar Online the controversy was a red flag for Biel's inner circle — this can be detrimental to any relationship if friends and family don't approve of a partner's behavior. "It's a lot, and her friends hate seeing her bogged down by all of this, and then having to deal with his humiliating arrest on top of everything else. They feel like Justin has been weighing her down for years, honestly," they claimed. 

Jessica Biel and Justin Timberlake were in other relationships before getting together. On January 5, 2007, Biel was with Derek Jeter in Puerto Rico. On January 11, 2007, Timberlake and Cameron Diaz called it quits after four years together. Only one week after that, Timberlake and Biel were seen at a Golden Globes after-party.

Timberlake admitted in his 2018 book, "Hindsight: & All the Things I Can't See in Front of Me," that he and Biel were casually dating others when they got together. "We were both still seeing other people, keeping ourselves safe from getting hurt, from really putting ourselves out there," he admitted (via Grazia). "It took a bit for both of us to admit to ourselves that we're really, really that into each other."

The red flag here? Professionals recommend taking a hiatus to fully recover from a breakup before dating someone new, and Kiaundra Jackson, LMFT, is one of them. "My rule of thumb after someone has a breakup is to have a period of detox," she told NBC News. "This is where you take time for yourself. You do not date. You do not have flings. You do not do anything that would be contradictory to your healing process." Stepping back allows for time to process the split and work out what happened. "If you don't address those things head on, you will be bringing the same baggage, issues and drama into your [next] relationship."