Britney Spears and Justin Timberlake: Revisiting Their Biggest Ups and Downs

A new chapter in the long-standing emotional drama between Britney Spears and Justin Timberlake — stemming from their romance decades ago — is once again playing out in public, due to claims made in the “Toxic” singer’s forthcoming memoir.

In her new book, The Woman in Me, the 41-year-old pop star writes about the time she allegedly got an abortion, after becoming pregnant with Timberlake’s baby. In an excerpt obtained by People, Spears claims that the “Cry Me a River” singer did not want to become a father.

This latest development regarding the former couple comes more than two years after Timberlake issued a public apology to Spears in February 2021, over backlash directed toward him due to the documentary The New York Times Presents Framing Britney Spears.

Throughout the documentary, footage shows Spears being put in the hot seat and questioned about her role in the highly publicized breakup, while Timberlake was seemingly idolized.

After watching the documentary, many viewers took to social media to express their “disappointment” and “disgust” in Timberlake. Many argued that he was to blame for the media’s negative portrayal of Spears after their split. 

With Spears’ memoir laying out new allegations regarding previously untold stories about their past romance, ET is taking a look back at the former couple’s ups and downs throughout the years.

Their Burgeoning Romance

Spears and Timberlake began dating in 1999, several years after they had been castmates together as teenagers on The Mickey Mouse Club.

In her highly anticipated new memoir, the “Not a Girl, Not Yet a Woman” singer also writes about the first kiss she shared with Timberlake, which happened when they were young teens, hanging out for an MMC sleepover.

“[Once] at a sleepover, we played Truth or Dare, and someone dared Justin to kiss me,” she writes, according to the outlet. “A Janet Jackson song was playing in the background as he leaned in and kissed me.”

In 1998, Spears opened for *NSYNC on their concert tour, and she later revealed that Timberlake asked her out in January 1999. 

Things Start to Get More Serious

While the pair spent months denying that they were dating, they finally went public with their romance in 2000 at the MTV Video Music Awards.

In September 2001, Spears revealed that she and Timberlake were living together — at least when they weren’t on tour. Speaking with The Guardian, the songstress revealed that Timberlake would stay with her at her home when they were both in L.A. She also expressed how her love for him had grown “deeper” over their two-year romance.

“We’ve gone through so much together and we’ve known each other since we were 12 years old,” Spears said. “We know each other inside and out.”

In February 2022, the pair made one of their last major public appearances at the GRAMMY Awards, where Spears was tapped to present the award for Best Pop Performance by a Group or Duo. While *NSYNC was nominated, the award ended up going to U2.

The Quiet Breakup

When it came to the end of their romance, there wasn’t any one specific moment or blow-out fight that signaled their love had come to an end.

Instead, the split was confirmed in more subtle ways — like Spears telling reporters in London, at the premiere of her film Crossroads in March 2002, that she was “not in an intense relationship with anyone at the moment.”

In November 2002, Timberlake elaborated on their split and detailed how much it hurt him to not be with Spears.

“It hurts too bad,” Timberlake told People at the time. “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.”

The Split Gets Complicated

The seemingly amicable breakup turned ugly days later in November 2002, with the release of Timberlake’s song “Cry Me A River,” which ostensibly launched his solo career. The music video for the megahit song featured the singer catching his girlfriend — played by a blonde actress, who many felt was supposed to be a stand-in for Spears — cheating on him.

While Timberlake denied that the song implied Spears had cheated, he later suggested exactly that in his own 2018 memoir, Hindsight & All the Things I Can’t See in Front of Me, saying that he’d “been scorned” and wrote the song in two hours in a fit of anger over their split.

In August 2003, Spears said she felt that Timberlake had been “exploitative” while doing press for the song and his album. “Every interview that he did, he was just talking about us in such an open way,” Spears said in an interview with Elle Magazine, adding that the video made her feel “freakin’ horrible.”

Justin Eventually Apologizes

After their split, both moved on to different relationships and career paths. Timberlake went on to marry Jessica Biel. Together, they share sons Silas, 8, and Phineas, 3. Meanwhile, Spears became a mother of two with ex-husband Kevin Federline and subsequently was forced into a 13-year-long conservatorship that she was only freed from in November 2021.

Nearly two decades after his music video and the plethora of interviews in which he seemingly painted Spears in a bad light to promote “Cry Me a River,” Timberlake issued a public apology for how he handled their split.

The apology came in the wake of the documentary The New York Times Presents Framing Britney Spears, which led to major public backlash.

In response, Timberlake said in a statement that he’s “seen the messages, tags, comments, and concerns.”

“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,” the statement read, in part. 

“The industry is flawed. It sets men, especially white men, up for success,” the statement continued. “It’s designed this way. As a man in a privileged position, I have to be vocal about this. Because of my ignorance, I didn’t recognize it for all that it was while it was happening in my own life but I do not want to ever benefit from others being pulled down again.”

Timberlake admitted that he hasn’t been perfect “in navigating all of this throughout my career.”

“I know this apology is a first step and doesn’t absolve the past,” he added. “I want to take accountability for my own missteps in all of this as well as be part of a world that uplifts and supports. I care deeply about the wellbeing of the people I love and have loved. I can do better and I will do better.”

Spears’ New Memoir Makes New Claims

In an early release excerpt from The Woman in Me, published by People on Oct. 17, Spears claims that she got an abortion after becoming pregnant with Timberlake’s baby while they were dating because Timberlake did not want to become a father.

“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,” Spears wrote about the pregnancy via People.

“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,” Spears’ claims.

Following the publication of Spears’ claim, a source told ET on Tuesday that, with the upcoming release of Spears’ memoir, Timberlake is looking ahead to the future.

“Justin has been focusing on his own family and trying not to concern himself with Britney’s memoir,” the source says. “In recent years, Justin has tried to be supportive of Britney from a distance. They dated so long ago, but he still has respect for her. Justin and Jessica just want everyone to grow and evolve instead of continuing to bring up the past.”

The Woman in Me is available for pre-order and is set to be released on Oct. 24.

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