Justin Timberlake and Alisha Wainwright seen leaving same trailer on movie set in New Orleans

Jessica Biel 

The couple married in 2012 after dating for five years and share a son, Silas, aged four.

Justin revealed in his memoirs that they met at a party and he fell for her when she was the only one who laughed at a joke he made.

‘We were both still seeing other people, keeping ourselves safe from getting hurt, from really putting ourselves out there.’ he wrote.

‘It took a bit for both of us to admit to ourselves that we were really, really into each other.’

They amicably announced their breakup through reps in March 2011 but by July an Us Weekly source said they were ‘quietly seeing each other again.’

He proposed in Montana in December 2011 and they held a sumptuous wedding at a resort in Puglia, Italy in 2012.

Jessica and Justin in 2018 at the Emmy awards

Cameron Diaz 

The A-list couple began dating in 2003 and announced their breakup at the beginning of 2007.

They apparently met when she gave him the Kids’ Choice Award for Best Burp onstage in 2003, two years after she got the same gong.

Their breakup occurred amid a storm of rumors about his infidelity with his What Goes Around… Comes Around music video co-star Scarlett Johanssen.

Scarlett responded to the conjecture in Seventeen: ‘We live in a world today where if two people are single – and one’s a guy and one’s a girl and they’re both famous – you’re going to be linked with somebody.’

She added: ‘If it’s somebody one week, it’s going to be somebody else the next week. It’s either me or Jessica Biel.’

Justin and Cameron announced their split in January 2007. Later that month People reported they had a blowout fight at a Golden Globes afterparty when she marched up to him while he was in conversation with Jessica.

Four years after their breakup, however, Justin and Cameron could be seen starring together in Bad Teacher. 

Justin and Cameron seen here in 2007

Justin and Cameron seen here in 2007

Tatyana Ali 

Justin Timberlake and The Fresh Prince of Bel-Air actress briefly dated back in 2003.

She went on to marry Stanford professor Vaughn Rasberry in 2016 and the couple have a three-year-old son called Edward.

Alyssa Milano 

Justin and the Charmed star dated for a few months in 2002. 

On the Australian breakfast show Rove and Sam in 2016, Justin revealed he had a crush on her when he was a child and she was on Who’s The Boss.

‘Then we dated briefly, so that got weird,’ he quipped. ‘I was like: “Hey, I used to be obsessed with you when I was a kid.”‘ 

Jenna Dewan 

Channing Tatum’s ex has admitted she and the SexyBack singer dated in 2002, following his split from Britney Spears.

She said on Watch What Happens Live that she was his backup dancer ‘like, during-after the breakup’ with Britney.

According to Jenna the relationship was ‘not that long, guys. We were like friends, friends that then dated, and then we’re just really good friends now.’ 

Britney Spears 

Justin and Britney Spears dated between 1998 and 2002 – including their iconic double denim appearance at the 2001 American Music Awards. 

They met as children while both were members of the Mickey Mouse Club amid a group that included Christina Aguilera.

She famously opened for his boy band NSYNC in 1998. Three years later, Britney, NSYNC and Aerosmith played the Super Bowl halftime together.

There were rumors she lost her virginity to Justin but her mother Lynn wrote in her memoirs that Britney was 14 when she first had sex.

When they split in 2002 there was unconfirmed conjecture that the breaking point was her infidelity with choreographer Wade Robson.

Wade featured in the Leaving Neverland documentary where said that when he was a child he was sexually abused by Michael Jackson.

Britney and Justin at the 2001 American Music Awards

Britney and Justin at the 2001 American Music Awards

Veronica Finn 

Justin began dating Veronica in 1996 when he was 17, already in NSYNC, and she was 16 in the girl group Innosense.

In 2012 she told Star: ‘I was a “girl version of Justin.” We hit it off right away.’ She shared: ‘Our love was unique, and he was an absolute sweetheart.’

Veronica worried that Justin was unfaithful while touring and so they split, but she confessed in 2012 that she has held onto a box of pictures, letters and other items to remember the relationship by.


JT dated the Black Eyed Peas songstress way back in 1996.

The pop star, whose real name is Stacy Ann Ferguson, admitted on Watch What Happens Live that their fling wasn’t ‘all that serious.’

Read more at DailyMail.co.uk