Justin Timberlake's relationship with Britney Spears, fling with Cameron Diaz and marriage with Jessica Biel

With Spears dancing to his songs and Diaz having already worked with him twice since their split, here's a look at Timberlake's biggest flames

                            Justin Timberlake's relationship with Britney Spears, fling with Cameron Diaz and marriage with Jessica Biel
Justin Timberlake with Britney Spears, Cameron Diaz and Jessica Biel (Getty Images)

Britney Spears just gave us newer goals on how to be friends with your ex. Hopping on the TikTok bandwagon, the OG Popstar danced her heart out to a song by none other than Justin Timberlake, tagging him and complimenting him for the track in her Instagram video of the same. But Spears wasn't the only former-beau of Timberlake who made it to the top trends in the US; trending alongside Spears was Timberlake's ex-fling Cameron Diaz, who can't stop gushing about how much she adores being a mom these days.

Considering the reason why Timberlake has trended and made headlines in the recent past is a full-blown scandal where the married pop star was seen holding hands with a co-star on-set, let's take a look at how the former NSYNC member has consistently found the industry's hottest, most gorgeous women on his arms, before finally hitting gold with Jessica Biel. 

Relationship with Britney Spears

Britney Spears and Justin Timberlake attend 2001 MTV VMAs in their iconic matching denim outfits. (Getty Images)

Having first met on 'The Mickey Mouse Club' when they were probably 10 max, Timberlake and Spears finally saw sparks flying between themselves some seven years later. It all started when Timberlake was touring with his boyband and Spears was the opening act. Thus began their high profile relationship of four years, which also saw the world scarred by the two's matching denim outfits at the 2001 VMAs. From performing at the SuperBowl together to attending basketball games with matching jerseys, embedded with their nicknames for each other, they were pretty much the music industry's Royal Couple, with rumors suggesting Timberlake was Spears's first lover. Starry-eyed, Spears had told The Observer in 2001: "When people get too personal it bothers me. But 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".

Sadly, that 'everything' reportedly blew up when Spears cheated on Timberlake with her choreographer Wade Robson. A heartbroken Timberlake was quoted by The Telegraph, admitting: "The break-up was absolutely heartbreaking for me. I can't just have meaningless relationships with women. I have to find miss right in order to have a relationship. There's got to be that big moment when she comes along." The breakup however gifted their fans with two solid songs from each of them: Timberlake's 'Cry Me a River', and Spears's 'Every time'. Almost two decades later, it looks like water is finally under the bridge now as Spears couldn't be happier with her fitness guru beau, Sam Asghari.

Fling with Cameron Diaz

Actress Cameron Diaz and singer Justin Timberlake watch the Los Angeles Clippers take on the Los Angeles Lakers on April 9, 2006 at Staples Center in Los Angeles, California. (Getty Images)

A relationship between a singer with three Emmys and 10 Grammys, and an actress with four Golden Globe nominations might look like it was written in the stars, but Timberlake and Diaz's fling of sorts reportedly fell prey to jealousy. But the four years it lasted, things were both miraculous and hilarious at the same time for a couple who endured pretty much everything from tabloid libels to paparazzi attacks. It all started at the 2003 Kids' Choice Awards when Diaz presented Timberlake with the 'Best Burp' award. From that, they went on to attend charity sporting events in matching jerseys and even starred on 'Saturday Night Live' together, ticking off all the boxes for couple goals, before Timberlake's 'What Goes Around Comes Around' happened and it all fell apart.

According to Us Weekly, Diaz grew exceedingly jealous of the music video's star, Scarlett Johansson, who later had to shut down rumors about an affair between her and Timberlake in an exclusive with Seventeen. Diaz and Timberlake announced their split in Janurary 2007, but things got even worse at Prince's Golden Globes after-party that year, when she spotted him chatting with his now-wife and baby mama Biel. People had reported that a 40-minute confrontation ensued between Diaz and Timberlake in a side room, with the latter slamming his fist at a cabinet. Things got better between them in the years to come though, with both reuniting twice to work together after that very public break up. Diaz is happily married to 'Good Charlotte' guitarist Benji Madden and the two share a baby girl too.

Marriage with Jessica Biel

Actor/singer Justin Timberlake and actor Jessica Biel attend The 75th Annual Golden Globe Awards (Getty Images)

In Timberlake’s 2018 memoir, the former boyband member documented and nailed the coffin on how it all started with his lady-love, Biel, addressing that Golden Globes after-party and how it pretty much solidified everything between the two. “Then the Golden Globes came up, and that’s when we planned on seeing each other,” he wrote. “We were both still seeing other people, keeping ourselves safe from getting hurt, from really putting ourselves out there. It took a bit for both of us to admit to ourselves that we were really, really into each other.”

Beginning in 2007, the couple's romance fizzled briefly in 2011 when they announced their breakup in March, only for Timberlake to propose to Biel the same year, in just nine months. The two tied the knot in 2012 with Biel in a pink dress and Timberlake crooning a special song as she walked down the aisle at their Italian countryside wedding. In just three years, they welcomed their first child, Silas Randall. Things were great, with the two of them 'inspiring each other', attending Emmys together, giving us some stronger couple goals and making Haloween appearances in hilarious costumes. on for late 2019 to hit them like a brick.

Timberlake was photographed holding hands with his 'Palmer' co-star, Alisha Wainwright, something that he labeled a result of heavy drunkenness in an open Instagram apology dedicated to his wife. But once again the couple proved nothing really can get in the way of their relationship as they went on to celebrate birthdays together with love and laughter in 2020, even though headlines will have you convinced that Biel has Timberlake on a tight leash these days. Following the scandal, Biel reportedly wanted him to undergo a lie detector test, and later, be more of a stay-at-home dad to earn back her trust. But as long as the two are calling each other their 'timeless' loves, fans should be too worried. All seems well.

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