In 2022, Justin Timberlake and Jessica Biel celebrated a decade of marriage. Biel shared her happiness about reaching this milestone with Access Hollywood, despite acknowledging that their relationship has had its ups and downs.
Before anyone criticizes us for discussing their marriage, remember that this information has been publicly available for years. Anyone can find it with a quick online search. We’re not sharing anything new, and we’re not the only ones who’ve noticed some issues in their relationship. According to an insider who spoke with Us Weekly, despite their frequent displays of affection on social media, their close friends think it’s only a matter of time before Justin or Jessica decides to end things.
We’re about to dive into some serious gossip, so get ready. And if you need a snack to go with the drama, check out rrgsnacks.com for delicious options like beef and bacon jerky, buffalo ranch popcorn, and green apple licorice.
Before dating Jessica, Justin had a tumultuous on-again, off-again relationship with actress Cameron Diaz that lasted nearly four years. During a guest appearance on The Ellen DeGeneres Show, Ellen teasingly asked Justin when he planned to propose to Cameron, even joking about needing to buy her bridesmaid dress. Justin laughed and said, “You know what? Go ahead and reserve one. Just make sure you stay the same size for the next 15 years.”
Justin and Cameron ended things in late 2006 but didn’t make it public until January 2007. A few days later, they bumped into each other at Prince’s Golden Globes after-party at a Hollywood nightclub. Jessica, who was starring in Seventh Heaven at the time, was also at the party. She and Justin met for the first time, chatting with mutual friends when Cameron approached them.
Jessica politely excused herself, leaving Justin and Cameron to have what was reported as a heated 40-minute argument. Witnesses said Justin ended up with his head in his hands and, in a moment of frustration, slammed his fist into a cabinet, reportedly damaging it.
Despite the tense encounter, Justin was keen on getting to know Jessica better. He got her number, and they kept in touch while he was on tour. In an interview with Us Weekly, Justin said they talked on the phone constantly for the next two weeks. As they got to know each other, his interest in her grew, while Jessica was already imagining their future. She even sent an email to a friend, saying, “I know I’m going to marry this man.”
After his tour ended, Justin returned home and spent an entire month with Jessica. During that time, he realized he was ready to settle down and asked her to be exclusive, and she happily agreed. By May 2007, just four months after they met, Jessica joined him on the European leg of his tour. Things were going so well that rumors started circulating online that Justin had asked Jessica to move in with him. In June 2008, an insider told Just Jared, “They’re both really excited. They’re definitely headed for marriage.”
But as Valentine’s Day 2009 approached, a friend told Us Weekly that Justin had broken up with Jessica because he wanted to experience single life again. Jessica reportedly begged him to reconsider, and they patched things up until July 2009, when Justin took a boys’ trip to Vegas. Jessica was said to be constantly calling him while he was away. An insider shared, “She’s extremely needy and always keeping tabs on him. All of Justin’s friends find her really annoying. She’s always trying to fit in with the guys, but she and Justin just don’t have any chemistry.”
Then in November 2009, Us Weekly reported that Justin was spending time with Rihanna, and afterward, he took Jessica on a trip to North Carolina, only to break up with her again. A mutual friend of the couple told the publication, “He told her he was done. She was too much to handle.”
It seems the couple had a pattern of breaking up and making up, with someone in their circle always ready to spill the details to gossip magazines.
Tensions rose again in April 2010 when Justin Timberlake was cast in Bad Teacher alongside his ex-girlfriend Cameron Diaz. According to a friend of the couple, “He tortured Jess by taking this role, and they are reaching a breaking point.” The insider claimed that Justin and Cameron were flirting on set, and the more territorial and demanding Jessica Biel became, the closer Justin seemed to get to Cameron.
The same source said, “Justin would never marry Jessica,” and added, “When she’s not around, he’ll make fun of her to his friends.”
Apparently, Justin was disrespecting Jessica both to her face and behind her back. But Cameron wasn’t Jessica’s only concern. In September 2010, Us Weekly reported that Justin met actress Olivia Munn at a MySpace event. After exchanging numbers, Justin allegedly began pursuing Olivia, begging her to meet up. Online sources claim Olivia resisted his advances, saying she wasn’t interested if he was still dating Jessica. Justin reportedly told her he and Jessica were over, leading Olivia to believe he was single. They allegedly met up in New York, having a three-day fling that included a hotel stay, according to Us Weekly.
In 2011, Justin continued to show his lack of interest in Jessica. She threw him a surprise 30th birthday party and gave an emotional speech in front of the guests. Witnesses claimed Jessica was in tears as she reminisced about the day they met and expressed her love for him. According to Glamour magazine, Justin was so embarrassed by Jessica’s speech that he allegedly stood up and shouted, “Yeah!” to divert attention away from her.
Shortly after the party, Justin reportedly told Jessica, “You thought I was feeling you?” and admitted he didn’t want to marry her.
They quietly broke up, and after Justin was spotted getting cozy with his Friends with Benefits co-star Mila Kunis, rumors of cheating surfaced. Justin and Jessica released a statement to officially announce their breakup. A friend told Us Weekly, “Justin had been aggressively trying to end things with Jessica for the past month.” Another insider added, “He hasn’t been happy with Jessica for close to two years.”
This seems to be their longest breakup yet. After a few months apart, Justin had a change of heart. He told Vanity Fair that Jessica was the most important person in his life and started thinking seriously about the future, including marriage and family. Jessica took him back. They got back together in the summer of 2011, and by December, they were at their shared property in Montana. They went snowboarding, and in the middle of the snow, Justin proposed, and she said yes.
News of their engagement spread quickly, and everyone was genuinely happy for them. Well, almost everyone.
A writer for the gossip website Celeb wrote, “Everything seems back on track for Biel and Timberlake, and by ‘on track,’ I mean that everything is a complete mess. But Jessica won’t stand up to Justin because she’s so hypnotized by the idea of becoming a bride.”
We love juicy gossip, but we weren’t sure if the website was speaking facts or just hating on Justin and Jessica. As we kept reading, it became clear that an insider close to the couple was feeding the website all their private details. The insider said Jessica’s family wasn’t happy about the engagement because they were unsure of Justin’s intentions. The insider added, “Jessica’s dad and mom will never forget the hurt Justin caused their daughter.”
The website also claimed that after their engagement, Justin allegedly went back to his bad-boy ways, and Jessica was finding, quote, “phone numbers from girls in his pockets.”
Despite everything, Jessica and Justin went ahead with their wedding plans, and Jessica reportedly took an unusual step to ensure Justin’s loyalty.
According to the New York Daily News, Jessica had her lawyer draft a lifestyle clause. This document can include things like weight requirements for partners, frequency of intimacy, and ultimatums about infidelity. Supposedly, Jessica made Justin agree to pay her $500,000 if he ever cheated. If you need to go that far, maybe getting married isn’t the best idea.
They got married in Italy in October 2012 and welcomed their first child in April 2015. Everything seemed fine until October 2019, when Justin was seen holding hands with his Palmer co-star, Alicia Wainwright, during a night out in New Orleans.
Justin later apologized on Instagram, insisting nothing else happened with Alicia. However, an insider told Us Weekly that Justin and Jessica struggled to move past the scandal and even talked to lawyers about a potential divorce and what assets Jessica would get. The source said, “Jessica used to overlook Justin’s behavior, but she was ready to set new rules to keep him in check.”
People magazine reported that they went to couples counseling because Jessica was determined to fight for their marriage. But was Justin equally committed?
Another source said Justin went all out to make things right, sending Jessica gifts, flowers, and messages calling her “the hottest wife and mom in the world.”
In July 2022, they announced the birth of their second child. Some online users cruelly called the baby a “Band-Aid baby,” implying the child was conceived to save a rocky relationship. As of now, the couple has put their $35 million Los Angeles mansion up for sale and moved to Tennessee, away from the Hollywood spotlight. Hopefully, this change will bring them peace and happiness. Despite the glaring red flags, we wish Jessica and Justin all the best.