Strange Things About Justin Timberlake And Jessica Biel's Marriage

Justin Timberlake and Jessica Biel tied the knot in October 2012, and if you judge their marriage by their often-adorable social media output, they appear to be as fresh-faced and head-over-heels in love as they did when they first stepped out together. We're talking Paris selfies, loved-up throwback photos, and tropical family vacation shots that only the rich and fabulous can afford. 

If you remove the filter, however, it becomes clear that their marriage is not as conventional as they would have you believe. And no, we're not talking about Timberlake and Janet Jackson's infamous Super Bowl halftime snafu that had parents all over the world scrambling for the remote — that was long before Biel was in the picture. We're not even talking about Timberlake's other Super Bowl halftime show over a decade later, which he flubbed so bad The Atlantic dubbed it "a monument to underachievement" — even though that surely made for some awkward silence around the TimberBiel house.  

We're talking about the stuff that's kept this pair in the tabloids since their first public canoodle. Let's take a look at the stranger side of Justin Timberlake and Jessica Biel's marriage. 

Justin Timberlake and Jessica Biel first met through mutual friends and got to know each other at a 2007 Golden Globes after-party. The superstars' instant chemistry apparently proved too much for JT's ex, actor Cameron Diaz — the "Charlie's Angels" star reportedly got into a row with the former NSYNC singer when she spotted him chumming it up with Biel, per People. "The Sinner" star reportedly arranged for Timberlake to get her digits that evening, and while Timberlake insisted he did all the leg work early in the relationship, sources close to the couple paint a different picture.

According to Us Weekly, Timberlake told reporters from the Hollywood Foreign Press that "there is a thing called chivalry and it doesn't have to die with the birth of the internet. The way I see it, if you're asking a girl out on a date, it's only right to do it in a way that she can hear your voice. I had to be pretty persistent in order to get her to say yes." 

The thing is, he apparently didn't actually call right away. During a birthday party Biel threw for her partner years later, the actor gave a speech to friends and family in which she admitted that she took matters into her own hands and drove to JT's house after he failed to call the next day. One party-goer told the Daily Mail, "She quickly welled-up as she reminisced about the first time she met Justin and joked about how she virtually stalked him into going on a date with her."

When Justin Timberlake finally made the call, it didn't take Jessica Biel long to realize she wanted to marry him. The actor opened up about the romance's early days during a 2017 interview on "The Late Late Show with James Corden." "I have this email that is really funny that I sent to my producing partner Michelle [Purple], and it's literally like, 'OK, I can't make that meeting so I have to cancel, also I know I will marry this man, you can't tell anybody but your husband,'" Biel said. "I have no idea why I wrote that email, I don't know what he did that day, but I have this hilarious email."

The fact that the Minnesota native was so sure about spending the rest of her life with Timberlake at this early stage is even stranger considering most of their relationship at this point was conducted over the telephone. Biel told Corden that Justin's hectic touring schedule meant physical contact was rarely possible back then. "We didn't kiss for a very long time because he was on tour," she said, "and we were talking on the phone, like normal pre-teens do, we were just chatting on the phone for hours. So, we never really kissed for a very long time."

Both celebs tried to keep TimberBiel under wraps when they initially hooked up in 2007. Those rumors became impossible to deny after the pair was papped several times during a romantic city break to Rome in 2008, first enjoying a glass of wine in a pizzeria, then buying some genuine Italian gelato, and finally chewing each other's faces off down a side street. Photographic evidence meant Justin Timberlake and Jessica Biel were on their way to becoming a celebrity power couple whether they liked it or not.

Four years later, Biel told British GQ (via HuffPost) that Timberlake was the one part of her life she still owned, and she wanted to keep it that way. However, after they tied the knot the following year, these two both started down the slippery slope to oversharing. Nowadays, it's not uncommon to see the Timberlake and Biel declaring their love for one another on public platforms, with JT's Instagram feed sometimes walking a fine line between sweet and cringe-worthy.

Why did they suddenly start projecting an image of marital bliss? Well, it might have something to do with...

In 2012, Jessica Biel walked down the aisle to a song written and performed by her soon-to-be husband as part of a lavish ceremony in Italy — but the previous summer, it looked like TimberBiel was over for good. 

Rumors that Justin Timberlake and his "Friends with Benefits" co-star, Mila Kunis, carried on rehearsing for the steamy rom-com long after the shoot had ended gathered steam, coming to a head after they were spotted seemingly getting a little too close while promoting the flick together in the UK. "Justin couldn't take his eyes off Mila," one source claimed to the Mirror. "He was hanging on every word she said, and laughing a little too heartily at her jokes." While friends of the couple told People that Biel "always wanted to turn a blind eye" to the situation with Kunis, in the end even she allegedly started to believe the buzz.

The couple split, and while Timberlake's camp denied any shenanigans with Kunis, the pop star's arguably shady track record made his case a hard one to argue. The smooth singer has had to deny involvement with a number of celebs throughout his dating timeline with Biel, including Rihanna, Kate Hudson, Lindsay Lohan, Olivia Munn, Olivia Wilde, Scarlett Johansson, and Ashley Olsen. Whether there is any truth to the infidelity rumors or not, JT seems to be making a real effort to let the world know there's only one girl for him.

Another rumored catalyst behind TimberBiel's temporary implosion in March 2011 was the previously mentioned surprise party Jessica Biel threw for Justin Timberlake at his Mulholland Drive home in honor of his 30th birthday that January.

At the party, an insider claimed to the Daily Mail that Biel "gushed" over her man in a passionate and heartfelt speech — but instead of a romantic response from her one true love, JT reportedly got to his feet and yelled, "Yeah, b***hes," dismissing his future wife's words and shocking her friends. "It was really awkward," the source said. "Justin's reaction was almost disrespectful. He just laughed it off." 

Per the outlet, the pair had only just recovered from another cheating allegation wobble in November the previous year, and some insiders believed the "What Goes Around ... Comes Around" hitmaker's allegedly childish behavior could have well been the straw that broke the camel's back.

When it comes to Justin Timberlake gossip, there haven't been many better sources than Sadie Bomar, the star's brutally honest grandma, who claimed that Justin Timberlake was in no rush to head down the aisle with Jessica Biel. Sadly, Bomar died in 2018 at age 85, and her piping-hot tea spillage is greatly missed.   

According to a 2009 story in the Daily Mail, Bomar said, "He's busy writing new material and he works hard to be successful — he's really focused on that. As far as we're concerned, he's always been single. The girlfriends come and go, but we believe nothing has ever been serious. Justin does his own thing and he isn't ready to marry just yet." 

While these claims were denied by a source close to Biel, a friend of Timberlake echoed granny's sentiments. "Justin was dying to be single and have fun," his buddy told People. "He was torn, because Jess is an amazing woman and considered to be marriage material, and he loved that about her. But he couldn't drag her along just because one day in the far future he'd want to marry her. It was making her crazy, and it was making him hate himself."

Unfortunately for Jessica Biel, her relationship with Justin Timberlake temporarily hit the rocks around the same time his film career was starting to take off, meaning she missed out on some pretty fancy parties, including the biggest bash of all. 

When Timberlake attended the 83rd Academy Awards in support of best picture nominee "The Social Network" (he portrays Napster founder Sean Parker in the film), he didn't invite Biel to walk the red carpet on his arm. He brought his mother instead. While his split from Biel wasn't official at this stage, her absence from the 2011 event — at which Timberlake co-presented an award with rumored lover Mila Kunis — seemingly spoke volumes.

If Biel was bothered by that, she didn't let on. In fact, the actor posed for pics at a star-studded Vanity Fair Oscars Party at West Hollywood's Sunset Tower later that night, dropping jaws in a revealing gold Versace gown that showed a whole lot of chest and back. It also seemed to show Timberlake exactly what he would be missing if he refused to put a ring on it, and all of a sudden, the curly-haired heartthrob appeared to have a change of heart.

Justin Timberlake wasn't the only one to suddenly change his tune about marriage. His family also made a complete 180 on the subject. JT's loose-lipped granny Bomar was at it again as 2011 drew to a close, taking it upon herself to announce that TimberBiel was not only alive and well, but that her grandson had finally popped the question while the lovebirds vacationed in Wyoming. "He called me on Christmas Day and told me he's engaged," Bomar revealed to Gossip Cop (via USA Today). "The family loves Jessie ... she's a very sweet girl."

A sweet girl she may be, but a gullible one she is not. It reportedly wasn't long before engagement celebrations turned into sour discussions over a prenuptial agreement, with a source claiming to Star magazine (via SheKnows) that trust issues and a proposed fidelity clause were the main sticking points between the pair. "She thinks if he strays during the marriage, she should be royally compensated," the insider alleged. "She wants a fidelity clause in the prenup giving her at least $500,000 if he does. If he's faithful for several years, maybe she'll agree to have his baby. She doesn't trust him 100 percent yet. Jessica figures if she gets fat during the pregnancy, he'll cheat again."

After three years of marriage, Justin Timberlake broke the couple's baby news to the world in 2015 with an Instagram photo of him kissing Jessica Biel's baby bump. A few months later, they welcomed their son, Silas, to the world, ushering in what appeared to be a period of calm in their relationship. 

In her first post-baby interview, TimberBiel glowed as they chatted to E! News about the magic of parenthood. Timberlake even used his speech during his induction into the Memphis Music Hall of Fame to proclaim his love for his wife, calling her "beautiful, loving, and incredibly understanding of her husband's shortcomings."

If the shoe was on the other foot, however, would Timberlake be as understanding? In something of a role reversal, rumors emerged in 2016 that Biel was stepping out with a "mystery hunk" and was allegedly ready to call it quits with JT. There was also scuttlebutt that Timberlake and Biel were involved in a "nasty fight" over their joint fortune. "They're at war over everything these days," an insider claimed, "from Justin's rumored affairs to his demands that Jessica put her career on hold and have another baby."

Rumors of turmoil in camp TimberBiel began to fade in 2017, perhaps because the couple seemed to be consistently broadcasting their happiness. During an interview that May, Jessica Biel complimented her husband's charm and sense of humor. However, she raised eyebrows when she admitted that she doesn't want her son, Silas, to go into his daddy's line of work when he grows up.

"There are many qualities I'd love him to get from Justin," she told News.com.au. "But there's one thing I don't want for him — I really don't want him to be a musician." When pressed, Biel said she was "sort of" joking. "In reality, the music business is really tough," the actor explained. "I already have this image of him as a struggling musician and that's like, 'Oh my God!' As a mum, you think 30 years into the future and you're like, 'How do I fix this for him?'"

A few months later, Biel addressed her husband's influence again with family friend Jimmy Fallon on "The Tonight Show." Biel admitted she felt "a little intimidated" by her son's cool-kid behavior. "It's kind of like a mini-Justin," she said. "It's his style. He's got, like, a daddy swagger."

Jessica Biel worked hard to raise another "baby" — her kid-friendly LA restaurant Au Fudge — and dealing with an embarrassing lawsuit directed at her business possibly put a strain on her marriage.

In 2017, the actor was supposedly "freaking out" over being sued by former employees for allegedly pocketing staff tips worth $430,100, reported Radar. "This is very much Jessica's baby, work-wise," an insider said. "She's put her heart and soul into making it a success, so to have people accuse her of short-changing them has hit her hard." Justin Timberlake reportedly did his best to support her. "Justin's been trying to lift her spirits but she's gotten very little sleep and is glued to her work emails and phone while this mess is sorted out," the source said. "This is a very difficult time for her and Justin, for sure."

That September, the Daily Mail published photos of the couple leaving a New York restaurant. The paparazzi pictures show Biel seemingly storming off in front of her husband as he calls to her from a few feet away. "Neither one seemed to be in great spirits," the Daily Mail noted. To which we might shrug our shoulders and ask who hasn't enacted this same scene with a partner at some point in their lives? The lawsuit remained a potential relationship stressor until 2019, when The Blast reported that a confidential settlement had been reached. All parties involved were reportedly satisfied with the outcome.

2018 was a relatively uneventful year in the TimberBiel timeline. Sure, Justin Timberlake's fifth studio album "Man of the Woods" was savaged by critics and his big Super Bowl halftime show flopped, but he and his wife appeared happier than ever. They almost went drama-free for two straight years, but as 2019 drew to a close, this longtime Hollywood power couple found itself back in the headlines for all-too-familiar reasons.

In November of that year, video footage of an apparently inebriated Timberlake holding hands with his "Palmer" co-star, Alisha Wainwright, during a night out in New Orleans was obtained by The Sun. "They were smiling and laughing," an eyewitness claimed to the British tabloid. "At one stage he grabbed her hand and rested it on his knee. She then gently started stroking his leg. Then he clutched her hand with both of his and was playing with her hands."

As previously mentioned, Timberlake's seemingly shady behavior is well documented, including accusations that he's cheated on Jessica Biel with multiple women. While there's never been photographic evidence of his alleged infidelities, he appeared to have been caught red-handed this time. And yet, sources close to Timberlake and Biel told E! News that he just had a few too many that night and that they were "downplaying everything and trying to laugh it off as nothing." The source continued, "He says it was not a big deal, [the cast] were all hanging out together and that's the end of the story."

Alisha Wainwright was also quick to downplay those incriminating pics of her looking super cozy with Justin Timberlake on that New Orleans balcony. A rep for the star, who is best known for her role in Netflix's critically acclaimed series "Raising Dion," told Us Weekly, "There is no validity to this speculation. They are working on a project together." This sentiment had been echoed by multiple sources. "The video may look a way, but literally, it was nothing," one insider told People, while another insisted to E! News that there was "nothing going on between them." It seemed as though Jessica Biel was buying that, too.

The Sun reported that Timberlake's wife seemed to look "miserable" when she was spotted out in public for the first time following the Wainwright photos, but (unlike her husband on the night in question) she was still wearing her wedding ring. Another E! News source with knowledge of the situation admitted that Timberlake's actions were "definitely inappropriate and something that would make any wife uncomfortable," but also confirmed that TimberBiel was "going to move on" from the incident. "Their marriage will survive," the insider continued, adding, "He feels guilty and will make it up to her. She is very good to him and he knows how lucky he is." 

The word "lucky" barely seemed to cover it — if Timberlake could survive this cheating scandal without losing his wife, he was practically invincible.

When Jessica Biel didn't tell her husband "bye, bye, bye" as soon as she saw the photos of him with Alisha Wainwright, you'd think a grateful Justin Timberlake would have concluded that it was in his best interest to do a little public groveling. But according to Us Weekly, it reportedly was not his idea to admit to his fans that he had screwed up. "Jessica encouraged Justin to put out his statement on Instagram because she felt embarrassed by his actions and wanted him to take accountability," an insider dished.

But in the December 2019 statement in question, Timberlake claimed that it was his idea, saying that he had decided to address the flurry of stories about the touchy-feely scandal for the sake of his family. First, he insisted that "nothing happened" with Wainwright. While that might lead some to think he believed that the PDA the public could see with their own eyes was no big deal, Timberlake then expressed regret for his actions and admitted to doing something that Biel deserved an apology for (confusing, right?). 

"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. This was not that," he wrote. Timberlake blamed his inability to stop the feeling on his inebriation and ended the post with a plug for his and Wainwright's film: "Looking forward to continuing to make this movie and excited for people to see it."

Three months after Justin Timberlake popped the question, Jessica Biel was photographed rocking her engagement ring for the first time in March 2012. A jewelry expert told Us Weekly that its pièce de résistance, a cushion-cut diamond, was likely six carats. Other design elements included blackened platinum, a double halo setting, and two smaller stones in halo settings. The expert estimated its value to be around $130,000.

While Timberlake's ring choice was dazzling and distinctive, a source later told Us Weekly that it apparently wasn't something that Biel would have chosen for herself. "Jessica's stylist really wanted Justin to come to her when picking out and designing the ring. She obviously knows what looks best on Jessica, and what type of things she likes to wear," the insider stated. However, Timberlake purportedly ignored all of the feedback he received from his wife's stylist and went with what he wanted. "I had no say whatsoever [in the ring]. I don't micromanage," Biel confirmed to InStyle (via People), but added, "I'll be honest: He has better taste than I do."

Another source previously told Us Weekly (via Celeb***hy) that Timberlake allegedly wasn't so keen on Biel showing the ring off after he put it on her finger, and it wasn't because he was humble and didn't want everyone remarking on the size of the diamond. "She wanted to wear the ring right away, but Justin has been worried this will be a career killer," claimed the insider. (That's a career killer for him, not Biel.)

Ahead of Justin Timberlake's October 2012 nuptials to Jessica Biel, one of the "Suit & Tie" singer's friends filmed a tasteless video that was reportedly meant to be shown at the TimberBiel wedding reception. The pal, Justin Huchel, thought it would be funny to film people living in homelessness sharing well wishes for Timberlake and Biel, who paid millions for their wedding guests' stay at the luxurious Borgo Egnazia resort in Italy. One man who appeared in the video told TMZ he was paid $40 to recite something along the lines of, "Forgive me for not being at your wedding. My gift is going to be in the mail." When he was informed that he was being mocked in the video, he said, "That makes me feel really bad. I feel they played on me."

Unsurprisingly, the idea of the rich and famous laughing at the less fortunate didn't go over so well, so Timberlake issued an apology for the video on his website. He made it clear that he had nothing to do with its creation and said that it was not actually shown at his wedding, although Huchel's attorney revealed that this was the intention in a letter to Gawker. The tone of Timberlake's apology seemed strangely lighthearted overall, with the singer at one point trying to argue that the video was humorous. "I think it was made as a joke on me not having that many friends attending my own wedding (which IS kind of funny if you think about it)," he wrote (via Spin).

In a 2019 episode of "The Tonight Show," host Jimmy Fallon surprised Jessica Biel with a clip from a 1999 interview. In it, she was asked to share her thoughts about NSYNC and said of her future husband's boy band, "I'm not a huge fan. Um, but, I mean, cool. I guess." Biel explained to Fallon that she didn't listen to modern pop music at all when she was younger, saying that she preferred "old school" tunes such as the "Rent" cast recording and Motown. There's certainly no shame in that, but Fallon then asked her if she's listened to any NSYNC songs since she and JT became a couple. "Not really," she said. Biel recalled recently playing a game of Truth or Dare with friends and being dared to belt out an NSYNC tune in its entirety. "I literally — I couldn't," she said. "I only know three words: 'Bye, bye, bye.'" Justin Timberlake didn't let her get off that easily and helped her sing the rest of another song. "It was humiliating," Biel shared.

Later that year, Biel transformed into her husband for Halloween by rocking a curly wig and a blue jumpsuit. "This is what happens when you admit on TV that you don't know any NSYNC songs and you're married to @justintimberlake," she wrote on Instagram. On "The Late Late Show," she revealed that the shiny onesie was actually the same one that Timberlake wore to the American Music Awards in 1999.

When it comes to who makes decisions about Jessica Biel's wardrobe, Justin Timberlake might as well say, "It's gonna be may." In a 2018 interview with People, Timberlake revealed that there's one part of Biel's closet in particular that he has domain over. "A lot of times I'll push her to try something, like, 'You should own a pair of Jordans, just because,'" he said. "I do a lot of her shoe shopping; I love women's shoes." And if Biel doesn't like the sneakers or Manolo Blahniks that her husband picks out, she can always give them to their son, Silas, to play "Jurassic Park" with.

Luckily, Biel trusts her husband to make fashion choices for her because she believes that he has excellent taste, as previously mentioned. However, Timberlake doesn't simply go into her closet, choose an outfit, and lay it out for her like a mom trying to save time on a school day; he makes his wife work for his approval. "When I walk out of the closet after getting dressed in the morning, I'll go like this [turns palms upward as if to say, 'Well?']. And he goes like this [shakes his head no]. Then he picks again," Biel told InStyle (via People). "It's hilarious." It also sounds like a great way to run late all the time.

Jessica Biel has a brother named Justin, which is something that's kind of strange in and of itself. Her husband hired the other Justin to work for his company, Sauza 901 Tequila, but Justin Biel was no longer employed by the brand in 2011 when he filmed a series of bizarre, since-deleted Facebook videos complaining about Timberlake's marketing prowess and bashing the label. "I've been waiting for [Timberlake] to do something with this f***ing brand — make a song about it, put it in a godd**n video, hold it up, take some pictures," he said in one of them, per TMZ. JB's own marketing ideas, he claimed, were to film an X-rated video with his girlfriend and to physically assault people with bottles of the beverage. He also complained about the brand's dismal sales, joked about the tequila pairing well with cocaine, and suggested a few new slogans for it. They included, "901 Tequila: I only s*** my pants once on it" and "901 Tequila: so godd**n exclusive our own CEO doesn't even drink it."

Justin Biel admitted that nepotism likely got him his brand manager job, but he wasn't going off on his brother-in-law because he was bitter and ungrateful after parting ways with the company. He later claimed it was all a mere joke. However, a representative for the brand told TMZ that the plan was actually to use the videos to promote the tequila. "It was released prematurely without our knowledge and prior to the final edit," claimed the rep.

When Jessica Biel and Justin Timberlake were preparing for the arrival of their first child in 2015, they essentially acted as though they were gearing up for a UFC fight. "We had two midwives, one doula, one meditation birthing class, a ton of hippie baby books, and a lovely home in the Hollywood Hills that we had turned into a labor training facility that we called The Octagon," Biel recalled in the 2018 book "The Nannie Connie Way: Secrets to Mastering the First Four Months of Parenthood," admitting, "So, not exactly normal." The parents-to-be desperately wanted to have a home birth, but apparently, their son, Silas, decided that he'd rather not come into the world kicking and hammerfisting like Connor McGregor.

According to Biel, she was upset when everything went awry and she had to go to the hospital for an emergency C-section. Her response to losing control of her natural birth plan was to become one controlling crunchy mama after taking her son home. "I was obsessed with everything organic, toxin-free, natural, and homeopathic for our kid, who came into this world in an operating room through an incision. I was a dictator, making myself and my husband insane!" she continued.

This mommy autocracy had apparently lost its appeal by the time COVID-19 lockdowns started. In a 2020 appearance on SiriusXM's "The Morning Mash Up," Timberlake angered many parents without nannies by saying of himself and Biel, "We're mostly commiserating over the fact that just 24-hour parenting is just not human" (via HuffPost). The couple quietly welcomed son Phineas that summer.

When Justin Timberlake and Jessica Biel got hitched, People magazine paid the couple $300,000 for their wedding photos, per HuffPost. They had to share the cover with a tiny teaser image of Britney Spears in the righthand corner, but the smiling face of Timberlake's ex wasn't the only thing awkward about the cover; Timberlake was pictured leaping up in the air, a la Tom Cruise. Biel, meanwhile, was seated on the ground, which made it difficult to see many details of her gorgeous pink wedding gown. The focal point was arguably Timberlake.

When the couple announced that they were expecting their first child in January 2015, they didn't get another big payday from People — but Timberlake essentially made himself the center of attention again. On Instagram, he shared the aforementioned photo of himself kissing Biel's bare baby bump. Her face was cropped out of the shot, which made some fans mistake her belly for something else. "Oops, at first glance I thought you were kissing some guy's butt for an SNL skit or something!" one of JT's followers wrote. "LOL Sorry Jessica!"

In his caption, Timberlake also failed to acknowledge Biel's role in making him a parent. "Thank you EVERYONE for the Bday wishes! This year, I'm getting the GREATEST GIFT EVER. CAN'T WAIT. #BoyOrGirl #YouNeverKnow #WeDontEvenKnow #WeAreTakingBets," he wrote. (At least he switched to using plural pronouns in the hashtags.)

The specter of Justin Timberlake's relationship with Britney Spears still loomed large over the "Cry Me a River" singer more than two decades after the former pop power couple's 2002 breakup. Spears made a number of shocking revelations in her 2023 memoir "The Woman in Me," one of which was that she got pregnant with Timberlake's child. Although she didn't wish to, she decided to have an abortion when he allegedly told her that he didn't yet want to be a dad. She also accused her ex of being a frequent philanderer and breaking up with her in a text (via Us Weekly).

While Biel reportedly felt sorry for Spears, a source cited by Us Weekly claimed, "She thinks Justin's learned from his mistakes and deserves to live in peace." However, Britney stans seemingly had no plans to stop holding the past against JT. After the book's publication that October, both Timberlake and Biel's Instagram pages were inundated with angry messages. Timberlake turned his comments off, and Biel limited hers when Spears' fans started directing their ire at her instead. "How can you still be married to a man who destroyed your ex-girlfriend's psychological well-being? As a woman, you should put yourself in her shoes and have a minimum of empathy. But no, it's covering up everything this monster did," read one message. 

The timing of Spears' memoir release was especially bad for TimberBiel; a source told the Daily Mail that it reportedly cast a shadow over their anniversary.