Meet Justin Timberlake’s Wife & Look Back at The Celebrities He Dated Before He Settled Down

Jessica Biel (2007 – 2011, 2011 – Now)

Justin Timberlake is currently married to actress Jessica Biel. The couple was first romantically linked in 2007 following the singer’s split from Cameron Diaz. The pair briefly called it quits for a few months in 2011 before Timberlake proposed in December of that year.

“We were in Montana on a piece of property that we owned at the time,” Biel later recalled about the special moment on The Late Late Show. “We had snowboarded all day. It was in the middle of the winter. Waist-high snow. We were [in] head-to-toe snowboarding outfits — hats, gloves, everything.”

The lovebirds officially tied the knot in 2012 in an intimate wedding in Southern Italy. “I had a little bit of butterflies,” the Candy actress told People about the ceremony. “I was about to stand up in front of my friends and family and bare my soul for the person I love. It was terribly emotional.” A few years after their nuptials, they welcomed their first son, Silas Randall Timberlake, in April 2015.

Their relationship has had its ups and downs, and Timberlake specifically has battled cheating rumors over the years. In November 2023, he was spotted holding hands with his Palmer costar, Alisha Wainwright. “A few weeks ago I displayed a strong lapse in judgment — but let me be clear — nothing happened between me and my costar. I drank way too much that night and I regret my behavior. I should have known better,” Timberlake wrote in a statement at the time, per People.

In January 2021, their family grew slightly larger when they had their second child, Phineas. “I had, like, a secret COVID baby,” Biel revealed on Dax Shepard’s Armchair Expert podcast in June of that year. “It wasn’t like it was supposed to be a secret. It was just COVID happened, and then I went to Montana with my family and never left.”

They had a small vow-renewal ceremony in Italy to celebrate their 10-year wedding anniversary in 2022. Two years later, Timberlake faced controversy when he was arrested in Sag Harbor, New York, and charged with DWI on June 17, 2024. After the news broke of her husband’s arrest, Biel was spotted in Manhattan in a downcast while filming. A source told People that the arrest was a “distraction” for the actress and that “she’s not happy” about it. Another source told Us Weekly, “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.”

Cameron Diaz (2003 – 2006)

One of Timberlake’s most serious relationships was with Charlie’s Angels actress Cameron Diaz. The pair reportedly met at the 2003 Kids Choice Awards when she presented him with the award for “Best Burp.” They were together from 2003 to 2006.

While it’s unknown what caused their breakup, some rumors suggest that the pair disagreed on Scarlett Johansson’s role in his “What Goes Around … Comes Around” music video in 2006. Us Weekly reported that a “Timberlake’s pal” told them, “Cameron was very jealous of Scarlett … She could not believe he went behind her back to put her in the video.” The source also alleged that Johansson and Timberlake “definitely got together after she did the video.”

After months of attention from the tabloids, Timberlake and Diaz announced they had broken up. “We have, in fact, ended our romantic relationship, and have done so mutually and as friends, with continued love and respect for one another,” the former couple said in a joint statement.

Thankfully, there’s no bad blood between the ex-lovebirds. They reunited for the 2011 film Bad Teacher, where they even had a sex scene. Diaz told Us Weekly that it was not awkward to collaborate with her ex on the comedy. “No, it’s great. Justin and I have always had a good laugh together, and to make a movie where we get to have a laugh together, and there really was no one else who was more perfect for this part,” she explained.

Alyssa Milano (2002)

Alyssa Milano was also romantically linked to Timberlake in 2002, the same year he ended things with Britney and briefly dated Jenna Dewan. When Access Hollywood asked about her dating history in 2013, the Charmed star addressed whether she and Timberlake were an item. “Yeah that’s true, that was right after Britney broke his heart, I swooped in for the kill!” she quipped.

Two years later, Milano revealed that she was rooting for Spears and Timberlake. “They were super cute, super in love,” she told Entertainment Tonight in September 2015. “They just seemed like the perfect match!”

Unfortunately, Britney later accused Alyssa of bullying after Milano tweeted, “Someone please go check on Britney Spears,” in January 2022, according to Billboard. In response, Britney shared Milano’s tweet on her Instagram stories with the caption, “Ladies, we are supposed to be rooting for one another, not pulling one another down.” A representative for the actress told TMZ that Alyssa reached out to Briney privately to apologize.

Jenna Dewan (2002)

Following his breakup with Britney Spears, Timberlake went on to date one of his backup dancers, Jenna Dewan. It’s unknown how long they were together, but Dewan spoke about their brief fling during Watch What Happens Live With Andy Cohen in May 2017 (via Entertainment Tonight). “We dated, not that long,” she revealed. “We were like friends … that dated.”

She also insisted that she was “not the rebound,” and the rumored “dance-off” between Dewan and Spears, depicted in Lifetime’s unofficial biopic Britney Ever After, never happened. “So, this dance-off situation, it never happened, people! No! It was in tabloids and everyone thought this happened,” she explained. “I wish I could say that, but no, it never happened — not that I saw.”

The Step Up actress added that being around Timberlake during the “whole drama” of his breakup from Spears was the “craziest, wildest thing.”

Britney Spears (1999 – 2002)

Justin Timberlake and Britney Spears were among the hottest couples in the early 2000s. The singers first met when they were 11 years old on the set of the ’90s revival of The Mickey Mouse Club (Timberlake was even Spears’ first kiss!). They reunited in the late ’90s when both of their careers were taking off; Timberlake was a member of the popular boy band NSYNC, while Britney had just launched her pop career.

The pair reportedly started dating in 1998 after she opened up for NSYNC at their concert tour. However, Spears denied the dating rumors in her April 1999 cover story for Rolling Stone. Later, Spears recalled in an interview with Andi Peters that Timberlake first asked her out. “We were doing a radio show, and this was before Baby One More Time came out … He knocks on the door and he was like, ‘Can I see Britney?’ And [my assistant] Felicia [Culotta] didn’t know who he was and she was like, ‘No … Who are you?’ And I was like, ‘No! It’s Justin!’” she explained.

Spears and Timberlake hard launched their relationship at the 2000 MTV Video Music Awards. In 2001, they twined in those iconic matching denim outfits (you know exactly what we’re talking about) for the 2001 American Music Awards’ red carpet. “I’m not ashamed at all to say that I love him from the bottom of my heart. As far as love is concerned, with him, too much is not enough. He’s everything,” the Baby One More Time singer told The Guardian then.

Ultimately, the couple called it quits in 2002. Timberlake opened up to People after their heartbreaking split. “It hurts too bad,” he admitted. “You get to a point when you’re crying yourself to sleep every night. I feel like I’m in the middle of a soap opera. I honestly know what it’s like to have a broken heart.” He added that he will “always love” Britney.

When Spears later released her 2023 memoir, The Woman in Me, the singer revealed that she was pregnant with Timberlake’s baby during their relationship, but she chose to have an abortion. “It was a surprise, but for me, it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated,” she wrote in her book. “But Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young.”

Fergie (1996 – 1997)

Before Justin Timberlake dated Britney, he had a brief relationship with Fergie from 1996 to 1997. “He was 16 and I was 23,” the former Black Eyed Peas singer told Australia’s Courier Mail (per Us Weekly). “It was before he got real heavy with Britney.”

In 2017, Fergie was asked about their past on the “Plead the Fifth” segment during Watch What Happens Live with Andy Cohen. “It wasn’t all that serious,” the singer revealed about their time together. “Am I allowed to pass on this? Pass. Plead the fifth.”

After their split, Timberlake and Fergie worked together on the song “Where Is the Love?” with The Black Eyed Peas in 2003. Fergie went on to marry and divorce actor Josh Duhamel. They share a son, Axl Jack Duhamel.