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Evening Standard
Evening Standard
Entertainment
William Mata

A timeline of Britney Spears and Justin Timberlake's relationship

Britney Spears has finally released her hotly anticipated memoir The Woman in Me, which contains – along with several other tantalizing revelations – the details of how Justin Timberlake broke up with her. 

The 41-year-old singer states that the then-*NSYNC member ended their three-year relationship in 2002 by text message after she kissed her choreographer Wade Robson - something she has also now admitted to. 

Timberlake and Spears started dating in 1999, when the pair were still teenagers, and their relationship went through very public highs and lows, but the full details - at least from Spears’ side - have not been fully revealed to the public until now. 

Timberlake has not commented on any of the revelations made in The Woman in Me. 

Here are all the highs and lows of Justin Timberlake and Britney Spears' relationship. 

1990s 

Early 1990s 

Spears auditions for a Disney Channel revival of The Mickey Mouse Club but is considered too young for the role, aged nine. She returns to Louisiana and begins drinking and smoking at an early age. 

At age 13, she passes her audition and is included in The Mickey Mouse Club - where she becomes part of a cast that also includes Christina Aguilera and Ryan Gosling, as well as, more significantly, Justin Timberlake. The pair are regulars in 1993 and 1994, becoming friends.

Spears and Timberlake kiss for the first as part of a game of truth or dare. 

Late 1990s

Spears signs with Jive Records aged 15 in 1997 and quickly records albums ...Baby One More Time, released in 1999 and Oops!... I Did It Again, in 2000. She is marketed with a clean image of virginity. 

In her book, Spears says: "Given that I had so many teenage fans, my managers and my press people had long tried to portray me as an eternal virgin - never mind that Justin and I had been living together, and I'd been having sex since I was 14.”

Timberlake, meanwhile, forms boyband *NSYNC and takes longer to break through but is soon enough a household name. 

The two begin dating in 1999, Spears later saying she was "so in love with him it was pathetic". 

January 2001

Britney and Justin, in their most iconic photo (AP)

With the pair at the peak of their fame, they make their most infamous outing as a couple, both turning up to the American Music Awards red carpet wearing matching denim. 

“I still can’t believe that Justin was going to wear denim and I said, ‘We should match! Let’s do denim-on-denim!'” she explained in The Woman in Me. 

“At first, honestly, I thought it was a joke. I didn’t think my stylist was actually going to do it, and I never thought Justin was going to do it with me. But they both went all in.”

Spears continued: “The stylist brought Justin’s all-denim outfit, including a denim hat to match his denim jacket and denim pants. When he put it on, I thought, 'Whoa! I guess we’re really doing this!'”

September 2001

Spears’ first single from third album Britney is I'm a Slave 4 U, a love song said to be about Timberlake. She follows this up with a performance at the VMAs where she carried a live python around her neck.

“All I knew was to look down, because I felt if I looked up and caught its eye, it would kill me,” she said in an Instagram post. 

2002

Timberlake leaves *NSYNC to pursue a solo career and later releases his first album Justified. 

Around this time, Spears and her choreographer Wade Robson have a fling that TMZ describes as an “all-night make-out session”. 

Songwriter Annet Artani, who worked with Spears, told TMZ that Spears at this point wrote Robson a 14-page break-up letter and hid it in her makeup bag - where it is found by Timberlake. 

Spears is filming a music video for her single Overprotected when she receives, according to The Woman in Me, a text from Timberlake reading, “It’s over!!!”

According to Page Six, the music video director Chris Applebaum finds Spears sitting cross-legged and in tears some way through the shoot. 

He tells Spears: “If you don’t have it in you, I totally understand … but if you want to go out there and finish this last set-up in the rain, you can show him that he just made the biggest f***ing mistake of his life.”

Spears says: “You know that? That’s a good idea. I’m going to show him that he blew the best thing he ever had.”

November 2002

Timberlake releases his second solo single Cry Me a River, which he wrote after an argument with Spears. The lyrics portray a brokenhearted man who is moving on from a lover who has wronged him. 

Spears says in The Woman in Me that Timberlake had cheated several times whereas she had only once. "In the news media, I was described as a harlot who'd broken the heart of America's golden boy. The truth: I was comatose in Louisiana, and he was happily running around Hollywood."

2003

Spears has a fling with Colin Farrell that she would later call a “two-week brawl”. 

"For a brief moment ... I did think there could be something there,” she says in her book but says she was not over Timberlake at this point. 

At the MTV Video Music Awards in 2003, Spears performs with Aguilera and Madonna - and she kisses the latter on stage wanting to create “a moment”. 

November 2003

Spears releases her fourth album In The Zone, a record which spawned hits Toxic and Me Against the Music but was also seen to take the singer in a more sexualised direction. It is the final album in her early hot streak and her last one before 2007’s Blackout. 

At the point of release, she is interviewed by Diane Sawyer for ABC about her so-called provocative new direction. She calls the experience “completely humiliating”. With regard to questions around Timberlake she says, “I didn’t owe the media details of my breakup. I shouldn’t have been forced to speak on national TV, forced to cry in front of this stranger, a woman who was relentlessly going after me with harsh question after harsh question. Instead, I felt like I had been exploited, set up in front of the whole world.”

January 2004

Spears marries childhood friend Jason Allen Alexander but the pair divorce after 55 hours.

She said: "I didn't take it that seriously. I thought a goof-around Vegas wedding was something people might do as a joke. Then my family came and acted like I'd started World War III." 

May 2004 

Spears releases piano ballad Everytime as the third single from In The Zone. 

Lyrics are interpreted as being about asking a former lover for forgiveness, which led to a media frenzy about it being a potential follow-up to Timberlake’s song Cry Me a River. 

Sawyer had asked Spears at the time if Everytime was aimed at Timberlake, but Spears replied, "I'll let the song speak for itself”. 

The song reaches number one in the UK, her final noncollaborative effort to do so. But it is not the last time the song’s significance becomes noteworthy… 

September 2004

Spears marries Kevin Federline. They both star in reality TV series Britney and Kevin: Chaotic, something Spears later says was the “worst thing” she has put out in her career.

September 2006

Timberlake releases his second album FutureSex/LoveSounds, which includes hit single What Goes Around... Comes Around, which is interpreted to be another shot at Spears. Timberlake denies this, however. 

November 2006

Spears and Federline divorce. The pair had sons Sean (born August 2005) and Jayden James (born November 2006). The divorce is finalised in 2007. 

The Woman in Me is dedicated to her two sons and in the book, she opens up about depression after having them. 

Britney Spears has won praise for her memoir (PA Wire)

January-February 2007 

Spears reaches her lowest ebb. She is fighting a custody battle and grieving her aunt who had recently died. After a brief stint in rehab, she enters a California hairdresser and shaves her own hair after staff refuse. 

“Nobody seemed to understand that I was simply out of my mind with grief,” she says. “My children had been taken away from me."

2007-2012

After her meltdown, Spears is put under a conservatorship agreement where her affairs are handled by her father. 

This restricted her access to making decisions and how she spent money. 

“The conservatorship stripped me of my womanhood, made me into a child,” she said. 

In this period, Spears released her critically acclaimed 2007 album Blackout and then her 2008 album Circus. Her biggest ever grossing tour followed on. 

In 2011, she released her dance and dubstep orientated Femme Fatale album and then again toured the world. 

Timberlake marries actress Jessica Biel and the couple go on to have two sons. He releases his third album The 20/20 Experience, having moved into acting in intervening years. 

2020s

By 2022, Spears was finally free of the conservatorship agreement and married Sam Asghari in June 2022, but broke up in July 2023.

She has not released an album since 2016 but has now returned to recording music and returned to the charts this year with collaborations with will.i.am and Elton John. 

Ahead of the release of the book, Spears revealed that she had an abortion with Timberlake’s child back when they were dating in the early 2000s. 

"For me, it wasn't a tragedy,” she said. 

"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.

"If it had been left up to me alone, I never would have done it."

It then resurfaces that Everytime was actually written within the context of having the abortion.

The Woman I Am was released on October 24, which Spears said required a "lot of therapy" to get through.

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