15 Rumors About Jessica Biel And Justin Timberlake's Relationship

When Jessica Biel spoke to Glamour in 2010 about what falling in love is like for her, she revealed, "It hurts so good." But if every rumor reported about her relationship with Justin Timberlake were true, she'd be drowning in a river of tears with nothing good to cling to.

Biel and Timberlake have been dogged by reports about their relationship woes since they first started dating in 2007. In 2009, a source told the Daily News that Timberlake had said "Bye Bye Bye" to Biel and jetted off on a boys' trip after deciding that he'd had enough of her purported clinginess. "All his friends think she's really annoying. ... She and Justin have no chemistry," the insider dished. Tabloids and celeb blogs that predicted doom for the pair hit paydirt when they broke up in 2011, and the rumors about their split were so grim that reconciliation seemed like an impossibility. "He hasn't been happy with Jessica for close to two years. ... Justin said he was miserable," a source told Us Weekly.

But Timberlake and Biel rekindled their flame fairly quickly, which meant that they'd keep getting scorched by the tabloids over and over again. As of 2022, Biel seemed to believe that her marriage was worth taking the heat. "We've had our ups and downs like everybody and I'm just really proud of it," she told Access. But to hear the tabloids tell it, her relationship has been one long descent that's going to end in disaster.

Justin Timberlake dated Cameron Diaz before he and Jessica Biel fell for each other. By some accounts, Diaz had a difficult time moving on from her ex — or was Timberlake not yet her ex when Biel first caught his eye? In his memoir "Hindsight: And All the Things I Can't See in Front of Me" (via People), Timberlake admits that he was dating someone else when he arranged to meet up with Biel at the 2007 Golden Globes. According to a 2007 Page Six report, Diaz totally freaked out upon seeing Timberlake and Biel getting flirty at the event and confronted Biel at an afterparty. "If that's how she wants to get him back, it won't work," a source said. But perhaps the real issue was that Diaz didn't know she'd lost Timberlake to someone else.

Fast forward to 2010 when Diaz and Timberlake were filming the raunchy comedy "Bad Teacher" together. It doesn't take a good teacher to do the math and determine that this equation equals the potential for large sums of tabloid sales. An Us Weekly cover story about the exes working together claimed that Biel was not happy with her then-boyfriend. "[Timberlake] tortured Jess by taking this role. ... The truth is, I don't know if they can survive this." a source said. Another insider claimed that Biel's complaints to Timberlake about the situation were making him rethink their relationship instead of causing him to become sympathetic to Biel's supposed distress.

What goes around comes around? Rumors about Justin Timberlake being an unfaithful boyfriend were rampant during the early years of his relationship with Jessica Biel. In 2008, an eyewitness told the Daily News that they saw Timberlake leaving an NYC nightclub with Amanda Seyfried. "Amanda's no Jessica Biel, but they seem to enjoy each other's company," said the source, which ... ouch. That same year, an onlooker told Star magazine (via Celebitchy) that they saw Timberlake kissing "How to Lose a Guy in 10 Days" star Kate Hudson at a Hollywood hotspot. Timberlake didn't lose his girlfriend over the rumors, and maybe Biel was somewhat relieved that she wasn't the one being accused of cheating. The year prior, Star magazine (via Celebitchy) claimed that Biel had stepped out on the "Suit & Tie" singer with an ex now known for rocking an iconic star-spangled suit: Captain America himself, Chris Evans.

Biel and Evans dated for five years before calling it quits in 2006, so they hadn't been broken up all that long when Biel started seeing Timberlake. If Star's sources are to be believed, the exes couldn't stop those old feelings from resurfacing when they both attended a pal's wedding reception. "They were holding hands and cuddling all night — even trading little kisses!" one purported eyewitness said. Celebitchy noted that Biel and Timberlake hadn't yet gone public with their relationship at the time, so it's possible they weren't dating exclusively.

When Justin Timberlake and Rihanna hit the recording studio together in 2009, there was speculation that the former "Rehab" collaborators weren't just working on the "Rated R" bonus track "Hole in My Head." According to a Star magazine report, Timberlake was in constant contact with RiRi and had told her that he and Biel were on the outs. This is why the "Love the Way You Lie" singer purportedly had no qualms about treating Timberlake to a lap dance. "She is a total tease and loves flirting with him. She digs him and wants to date him too!" said one of the tabloid's anonymous sources.

A Rihanna insider denied that she was engaging in any such behavior, telling People that she and Timberlake's sole focus was their work, work, work, work, work, work. The National Enquirer also helped Rihanna out by publishing one of those unicorn tabloid stories that defends a celeb's reputation. A source told the outlet that Rihanna had personally reached out to Biel to assure her that there was nothing shady going on. "Rihanna has been cheated on in the past, and one thing she would never do is take another woman's guy," said the insider. Apparently, there were no hard feelings about the rumors — the following year, Biel told Vogue that Rihanna was one of her greatest sources of style inspiration. "She's got something going on that I am sort of craving a little bit," said "The Sinner" star.

In 2009, Lindsay Lohan tweeted and deleted a message that was assumed to be about Justin Timberlake. "Where's jb cheater," she wrote on X, formerly known at Twitter. The "JB" in question was seemingly not Justin Bieber but Jessica Biel, who was not with Timberlake when he was spotted partying at the same nightclub as Lohan, NYC's Avenue. Lohan followed that tweet up with another reading, "Why do people cheat?" The "Mean Girls" star later claimed that the musings about infidelity were not her own, but those of a hacker. However, a source told Us Weekly that no one had taken control of Lohan's account to question Timberlake's loyalty; Lohan had, indeed, posted the messages. She was reportedly scared into deleting them when Timberlake vowed retribution via what was the worst form of punishment for late-aughts LiLo: getting her banned from the nightclub where she committed the offense. Oh, and a source also claimed that he went full-on Regina George by threatening to "make her life miserable."

Another eyewitness told Page Six that Lohan sent the tweets in the first place because she was bitter about Timberlake brushing her off when she tried to dance with him. The source claimed that Timberlake later got flirty with another clubgoer — a situation that could have served as inspiration for Lohan's infidelity accusation. However, the club's owner claimed to possess surveillance footage proving that Timberlake wasn't rocking his body next to any women.

In 2010, Us Weekly reported that Justin Timberlake had hooked up with Olivia Munn. The two first met when Munn hosted a live chat event promoting Timberlake's movie, "The Social Network." A source claimed that Timberlake had more than socializing on his mind when he got Munn's number, and she invited him over to her NYC hotel the day after the event. According to the magazine, their affair lasted three days, and a source claimed to know that they "had amazing sex." The insider also said that Timberlake had told Munn he and Jessica Biel were no longer an item, something he was purportedly saying to other people as well. Another source defended the "other woman" in the salacious story when issuing this denial to People: "Olivia Munn is not that type of girl."

According to a January 2011 Life & Style story, Timberlake hadn't stopped pursuing Munn after Us Weekly published its piece about their rumored affair. A source claimed that Timberlake was still texting Munn two months later and letting some of her friends see his messages. "One said, 'My relationship is basically over,'" the insider recalled (via HuffPost). "The other said, 'I'm thinking about you.'" While Munn reportedly enjoyed the attention, she didn't fully trust Timberlake. "She's not expecting it to go anywhere — but she'd love it if it did!" the source dished. But when Timberlake and Biel broke up in March 2011, he didn't move on with Munn.

Screenwriter David Newman told the New York Post that Jessica Biel made it to the screen-testing stage for the sexy 2011 rom-com "Friends with Benefits." Had she gotten the part, Justin Timberlake would have played her love interest. Instead, it was Mila Kunis who found herself describing the special "sock" that Timberlake wore for their sex scenes. "I could pretty much see everything," she told the Advocate. Kunis had recently split from Macaulay Culkin, and Timberlake was still single when it came time to promote the movie, so there was naturally speculation that the pair possibly shared more than on-screen chemistry. "Justin is very interested in Mila," said an E! News source in March 2011. "They've been flirting, but so far nothing has happened."

According to another insider, Timberlake possibly ruined his chances with Kunis by trying to hit on her when they were filming the movie. At that time, he was still with Biel. "Mila knew he had a girlfriend and made it clear it wasn't going to happen," the source told Us Weekly (via Hollywood Life). Another insider added that Timberlake simply wasn't Kunis' type. 

By April 2011, Us Weekly was linking Timberlake to a different leading lady: his "In Time" co-star Olivia Wilde. However, she shot down the romance rumors by tweeting, "We are just friends and have been for years." That May, the New York Post reported that Timberlake was spotted chatting with both Wilde and Kunis at an "SNL" afterparty.

The cherry on top of Jessica Biel and Justin Timberlake's 2011 reconciliation was when Timberlake popped the question that December. Shortly after their engagement, OK! reported that Biel had been pursuing a proposal for a long time, modeling her supposed strategy on that of a member of the British royal family. "She's a big fan of Kate Middleton and saw how she remained aloof and kept quiet after Prince William dumped her, and now, she's a princess!" a source said. But the insider added that Biel had to endure a lot of pain to get than engagement ring on her finger. In 2009, Fox411 reported that she was even willing to try a "friend with benefits" arrangement to keep Timberlake in her life. According to an insider, Timberlake straight-up told her that he wanted to pursue other women.

If Biel watched Timberlake's 2006 appearance on "The Ellen DeGeneres Show," she would have known that patience was required to become his bride. When Ellen DeGeneres joked about getting a gown to be a bridesmaid in his wedding, Timberlake responded, "You will have to stay the same size for the next 15 years" (via TMZ). But not long after Timberlake and Biel got back together, Us Weekly reported that the "Selfish" singer had become just an iota more open to the idea of getting hitched. "Justin thinks marriage would hurt his career, but if Jessica threatened to leave, he'd do it," an insider said.

According to a 2012 National Enquirer report, Justin Timberlake only popped the question because he believed that Jessica Biel would kick him to the curb if he didn't demonstrate his commitment to her with some primo jewels. "He told friends that he has no intention of rushing down the aisle and he only went through with the engagement to get Jessica off his back," a source said. Once Biel got her ring, outlets including X17 questioned why she was continuing to be photographed with a bare left hand weeks after her engagement. The National Enquirer offered one potential explanation: She thought the diamond Timberlake picked out for her was too puny. "Jessica told Justin that although she was moved by his proposal, she wanted a ring with more bling," a source said.

Us Weekly didn't back up the Enquirer's claim that Timberlake offered Biel a ring redo, complete with another proposal. However, the publication did quote a source as saying that when it came time to design the ring, "Justin completely went rogue." Of the massive bauble that he presented to his future bride, the insider said, "I wouldn't necessarily say it fits her style." Biel later confirmed to InStyle (via People) that Timberlake did not consult with her about the ring's design. However, she complimented his choice by saying, "He has better taste than I do." Star magazine (via OK!) reported that Timberlake also dropped $250,000 on some pre-wedding jewelry for an enthusiastic Biel.

Did Britney Spears once dream of a day when she and Justin Timberlake would be able to catch up and fondly reminisce about choosing those iconic matching denim outfits? Or did she perhaps want to gossip with him about their famous fellow former castmates on "The All-New Mickey Mouse Club?" According to The U.S. Sun, Spears attempted to reconnect with Timberlake multiple times after he and Jessica Biel got married, but he wasn't comfortable with revisiting that chapter of his life. "He wouldn't disrespect Jessica by building a close bond back up with a serious ex," a source stated. "So Britney had to back off and accept he'd fully moved on." If OK! is to be believed, Spears didn't completely stop reaching out to Timberlake; the tabloid claimed that she sent him and Biel an assortment of baby gifts upon learning that the couple was expecting their first child in 2015.

In a 2011 interview with Vanity Fair, Timberlake revealed that it had been about a decade since he last spoke to Spears. "I wish her the best — that goes without saying," he stated. Per OK!, Timberlake had the opportunity to say this to Spears himself in 2022. The outlet reunited the couple in its readers' imaginations by claiming that Timberlake was speaking to his ex, a development Biel was supposedly unaware of. "They'll talk about the old days and how glad Justin is that she's found happiness," a source said.

It's not unusual for the rumor mill to churn out pages of stories about celebrity couples expanding their families long before they actually do. One of the earliest instances of Jessica Biel and Justin Timberlake experiencing this phenomenon came in 2011 when the National Enquirer reported that Biel had stopped taking birth control in a bid to tie Timberlake to her forever. "She's also telling her friends that she can't wait to be pregnant," said one of the tabloid's sources. But according to a 2013 Radar report, Biel and Timberlake had actually discussed their baby plans and Biel had begrudgingly agreed to wait a bit longer to get pregnant because of Timberlake's packed schedule. "He's told her he wants to be a hands-on father, and that won't be possible with everything he's got on at the moment," an insider said.

But when Timberlake's dearly departed gossiping granny, Sadie Bomar, weighed in on the couple's baby plans in 2014, she told Star magazine that Biel was the one to blame for her lack of grandchildren. "Justin has wanted to have children all his life," she said. "If it were up to him, they'd have a baby tomorrow!" The following year, the couple welcomed their son Silas.

The rumors about baby battles raged on after Timberlake and Biel became first-time parents. In 2017, In Touch reported that the couple was going to therapy because Timberlake wanted to have another child ASAP while Biel wanted to wait.

According to In Touch's 2017 report about Jessica Biel and Justin Timberlake butting heads over their family plans, Biel wanted to do the unthinkable for a celebrity couple of their caliber. "Jessica had planned to raise their kids without nannies," a source claimed. But two years earlier, OK! reported that Biel had already decided that she wanted some help — she was just going to be very selective about who she hired to take care of Silas. A supposed pal of Biel said that she had employed "two gay male nannies" who were recommended to her by some friends. "She didn't want any Swedish nannies around Justin," the insider said. The source apparently wasn't trying to say that Biel was xenophobic against Swedish people, but that she didn't want an attractive female nanny around who might catch her husband's eye.

We now know that the rumor about the mannies is hogwash, as is the report about Biel wanting no childcare help. Biel and Timberlake actually hired celeb nanny Connie Simpson, who included a story about the couple in her book "The Nanny Connie Way." While promoting it, she shared a bit of gossip about the couple's pre-baby expectations. "Justin was serious about having his sleep and his space and Jess was serious about she was having a home birth," Simpson recalled to ET, "and I was sitting there shaking my hand going, 'Lord have mercy. It ain't gonna play out in either way.'"

Let's hope that Justin Timberlake's idea of bringing sexy back doesn't actually involve telling a woman that she needs to get her old body back. In 2017, OK! reported that Timberlake was unhappy about Biel losing weight for her role in the USA Network series "The Sinner." The outlet suggested that Timberlake's dating history demonstrates his attraction to women with curvy physiques, and a source claimed that he was telling Biel "to eat more" to regain her own curves. In 2017, Radar (via OK!) similarly claimed that Timberlake wanted Biel to alter her slimmer figure by getting a breast lift. "That's offensive to Jess, who's hurt by the suggestion," a source said. That report has since been wiped from the internet, so make of that what you will.

The shoe was sort of on the other foot in 2009 when the National Enquirer reported that Biel's body being in tip-top physical condition was making Timberlake feel insecure. "Jessica's superior athleticism has Justin mortified," a source said (via Celebitchy). Timberlake reportedly couldn't keep up with Biel when they went jogging together and he didn't like having her healthy diet pushed on him. "The hunger pangs — and Jessica's health kick — are putting Justin in a bad mood," the insider added. Biel deciding to get bangs in 2012 supposedly put Timberlake in a bad mood, too. "Justin has begged Jessica to change [her hair] back," a source spilled to Radar.

A month after Jessica Biel and Justin Timberlake were first romantically linked in January 2007, Timberlake was reportedly spotted getting flirty with Scarlett Johansson, the star of his "What Goes Around ... Comes Around" music video. An eyewitness told Page Six that the pair spent a lot of time together at a Super Bowl weekend party, recalling, "Scarlett came up, leaned into him and did a sexy, little dance, grinding into his body." But Timberlake and Biel would become more serious in the following months, and Johansson married Ryan Reynolds in 2008. That same year, OK! reported that Biel had sought relationship advice from Johansson and coordinated a double date with her.

Fast forward to 2011 when Johansson and Reynolds were going through a divorce. According to the National Enquirer, Biel was concerned that Timberlake's interest in Johansson would be rekindled now that she was single. "Jessica is terrified the former lovers will pick up right where they left off. After all, he dated Jessica and Scarlett simultaneously at one point," a source said. In September 2011, Us Weekly seemed to justify Biel's supposed fear by reporting that Timberlake had visited Johansson's NYC apartment. However, their reps denied that this happened.

Biel seemed to shrug off the ScarJo rumors by signing on to star alongside her in the 2012 movie "Hitchcock." They even had a friendly conversation about Biel's honeymoon at the film's premiere when Johansson inquired about it. Per Us Weekly, Biel gushed, "It was like magic."

In 2019, Justin Timberlake and his "Palmer" co-star Alisha Wainwright were captured on camera holding hands at a New Orleans bar. The Sun also published a photograph of Wainwright smiling at Timberlake while resting her hand on the "Drink You Away" singer's knee. Soon, rumors proliferated online about how Jessica Biel felt about her husband's PDA with another woman. According to an Us Weekly report, Biel pushed for Timberlake to publicly apologize because she wanted him to experience a small taste of what she was feeling. "Jessica was very upset and embarrassed by Justin's behavior and thought it was completely inappropriate," an insider said.

In 2020, OK! claimed that Timberlake tried to prove just how committed he remains to Biel by assenting to a "midterm agreement" that would award his wife a majority of their shared wealth in a divorce if he were to ever go astray. Meanwhile, Radar reported that Biel was laying down the law in other ways, such as insisting that Timberlake considerably cut down on his time away from his family. "If Justin absolutely has to go on the road for any reason, even for a movie shoot, he's going to have to figure out how to bring the whole family. ... It's time for Justin to become a stay-at-home dad!" an insider said. According to Life & Style, Timberlake also promised to quit drinking, which he was doing when he got a little too friendly with Wainwright.

The tabloids clamored to provide updates on the state of Justin Timberlake and Jessica Biel's union after Britney Spears made some unflattering claims about Timberlake in her memoir, "The Woman in Me." Among them was her account of Timberlake getting her pregnant and pressuring her to have an abortion. According to Us Weekly, this revelation wasn't news to Biel. The outlet also reported that Biel felt sympathy for both her husband and Spears. "She thinks Justin's learned from his mistakes and deserves to live in peace," an insider shared.

However, other outlets have reported that Timberlake's past behavior is beginning to take a toll on his marriage. According to a 2024 In Touch report, Biel has struggled with the public perception of her husband becoming so negative. "She feels like she doesn't recognize the man she fell in love with and married. ... It pains her that people think she's married to a creep," a source said. Life & Style claimed that therapy wasn't helping the couple, and its insider invoked the title of a Spears movie when discussing their marriage: "They appear to be at a crossroads."

Timberlake seemed to fight back against the rumors about relationship troubles when he released his single "Selfish" in January 2024. "I ain't ever lettin' you go," he sings. And Biel told Marie Claire that she and Timberlake have something in common that keeps their marriage strong, saying, "We believe in loyalty."