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From Mickey Mouse Club to cheating rumours: Britney Spears and Justin Timberlake’s relationship timeline

The couple dated from 1999 to 2002

Brittany Miller
New York
Wednesday 18 October 2023 04:34 BST
Related: SNL mocks Justin Timberlake over Britney Spears apology

As the release of Britney Spears’ upcoming memoir, The Woman in Me, draws closer, some of her old flames have shared how they really feel about what could potentially be written about them in her book - most notably, Justin Timberlake and ex-husband Sam Asghari.

Asghari, who filed for divorce from Spears in August after just 14 months of marriage, revealed that he received an early copy of the book and revealed he was “proud” of his ex-wife’s major accomplishment. “I already read it and I’m very proud of her,” he recently told TMZ.

However, Spears’ ex flame and former NSYNC member, Timberlake, is reportedly “concerned” that she could paint him in a negative light. “He’s very curious what she’ll reveal from their relationship,” one source explained to Page Six. “It’s eating at him.”

According to an early excerpt obtained by People, the singer revealed in her memoir that she became pregnant while dating Timberlake and decided to have an abortion. “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,” Spears wrote in her book, adding that she had the abortion because Timberlake wanted her to.

“I’m sure people will hate me for this, but I agreed not to have the baby,” an excerpt from the book reads. “I don’t know if that was the right decision. If it had been left up to me alone, I never would have done it. And yet Justin was so sure that he didn’t want to be a father.”

“To this day, it’s one of the most agonising things I have ever experienced in my life,” Spears said.

In a recent US Weekly report, a source claimed that Timberlake has said he won’t “be happy” about the memoir’s release because “it goes after him hard.”

The couple began dating in 1999, when Spears was 17 and Timberlake was 18, until 2002.

Here’s a timeline of their relationship.

1992: Britney and Justin meet on the set of All-New Mickey Mouse Club

When they were only 12 years old, Spears and Timberlake met for the first time as cast members on the All-New Mickey Mouse Club, alongside other well-known names: Ryan Gosling, Christina Aguilera, Keri Russell, and JC Chasez.

Spears reflected on her time on the show in her memoir, as she wrote that her and Timberlake “quickly connected”. She also wrote about their first kiss, which happened because of a dare. “[Once] at a sleepover, we played Truth or Dare, and someone dared Justin to kiss me,” she wrote in the book, according to People. “A Janet Jackson song was playing in the background as he leaned in and kissed me.”

Reflecting on their relationship in 2006, Timberlake said in an interview with GQ that meeting Spears was love at first sight. “I was in love with her from the start,” he told the magazine. “I was infatuated with her from the moment I saw her.”

1999: The two go public with their relationship

Although Spears and Timberlake met seven years prior, their romance wasn’t confirmed until 1999.

2001: Britney and Justin are spotted together at multiple events and start living together

One year into their relationship, the couple were finally spotted on the red carpet together - including the iconic moment when they wore matching denim outfits to the 2001 American Music Awards.

“I confess that there was maybe a period in the ‘90s where I could skip over some of the outfits that were public, but the internet will never,” Timberlake told the Hollywood Reporter in February 2021.

In 2001, they also performed at the Super Bowl XXV halftime show together, where Spears, Aerosmith, and Timberlake’s NSYNC boy band all took the stage.

During an interview withTheGuardian in 2001, Spears said that their relationship was getting very serious, explaining that Timberlake “lives at her house with her when he’s in [Los Angeles]”.

She added at the time: “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.”

2002: The breakup with no clear reason

Timberlake, now 42, shared in an interview with Barbara Walters that he had made a pact with Spears, now 41, not to “say specifically why” they went their separate ways.

But when pressed about tabloid rumours that Spears had cheated on him, Timberlake didn’t try to clear her name. “We’re not perfect. I don’t judge anybody. It’s just young love. It’s just young love. It was a very intense relationship, that’s for sure,” he said at the time.

It was also the same year that Timberlake released the song, “Cry Me a River”, which featured a female actor in the music video that looked very similar to Spears.

2003: Britney speaks out about the relationship

One year after Timberlake’s interview with Walters, Britney had a sit-down interview of her own with journalist Diane Sawyer, who bluntly asked her what she had done wrong in the relationship.

“I think everyone has a side of their story to make them feel a certain way… and I’m not technically saying he’s wrong, but I’m not technically saying he’s right either,” she said of her ex, who had suggested that she had been unfaithful.

Much like Timberlake, Spears was also speculated to have made a song about their relationship and breakup, titled “Everytime”.

2021: ‘Framing Britney Spears’ drops

Over the years, both Spears and Timberlake have continued to reflect on their relationship, with the pop star even dancing to one of Timberlake’s songs and calling him a “genius”.

Following the release of the Framing Britney Spears documentary, Timberlake apologised to both Spears and Janet Jackson - for her wardrobe malfunction during their 2004 Super Bowl halftime performance - on Instagram.

“I’ve seen the messages, tags, comments, and concerns and I want to respond. I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right. I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism,” he wrote.

“I specifically want to apologise to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed I also feel compelled to respond, in part, because everyone involved deserves better and most importantly, because this is a larger conversation that I wholeheartedly want to be part of and grow from.”

That same year, Spears spoke out about her conservatorship for the first time and Timberlake used the event to show his support for the singer. “After what we saw today, we should all be supporting Britney at this time,” he tweeted.

“Regardless of our past, good and bad, and no matter how long ago it was... what’s happening to her is just not right. No woman should ever be restricted from making decisions about her own body. No one should EVER be held against their will… or ever have to ask permission to access everything they’ve worked so hard for,” he said.

The actor concluded: “Jess and I send our love, and our absolute support to Britney during this time. We hope the courts, and her family make this right and let her live however she wants to live.”

The Independent has contacted Timberlake’s representatives for comment.

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