Britney Spears And Justin Timberlake: A Relationship Timeline Marked By Highs And Lows

Britney Spears and Justin Timberlake's journey started in 1992 when they were cast in the '90s revival of "The Mickey Mouse Club." Both were just 11 years old at the time, but they had an instant connection.

Timberlake even recalled their first kiss, which happened during a sleepover with their fellow castmates. Spears described that time as one of the most special moments in her life.

After the show, Spears and Timberlake went their separate ways as they pursued their careers. However, fate brought them back together in the late '90s when Spears opened for *NSYNC on their "In Concert" tour.

Timberlake asked her out, and their romance began to bloom. Spears fondly remembered the moment he came knocking on her door, asking for her, even though her assistant didn't initially recognize him.

After months of speculation, Spears and Timberlake decided to make their relationship public at the 2000 MTV Video Music Awards. Although they walked the red carpet separately, their affectionate behavior during the show left no doubt about their love for each other.

Spears' iconic VMA performance, a mashup of "Oops!... I Did It Again" and "Satisfaction," along with her sparkling nude ensemble, further fueled public fascination.

At the 2001 American Music Awards, Britney Spears and Justin Timberlake made a memorable appearance in matching denim outfits. Designer Steven Gerstein revealed that it was the couple's idea. Gerstein said:

"It was a no-brainer. Justin and Britney were dating at the time. They came up with the idea of matching denim. It was like their own prom. We brought their vision to life, and the rest is history."

During the Super Bowl halftime show, Britney Spears and Justin Timberlake, along with *NSYNC and Aerosmith delivered a thrilling performance. They sang "Bye Bye Bye" and "I Don't Want to Miss a Thing."

Spears, Mary J. Blige, and Nelly later joined for a collaboration on "Walk This Way." Backstage, Spears discussed her relationship with Timberlake, emphasizing trust and their mutual love.

Spears and Timberlake's relationship deepened, and they even lived together at her house in Los Angeles. Spears emphasized her profound love for Timberlake, which had grown since their initial meeting at the age of 12.

The couple collaborated on the song "What It's Like to Be Me" for Spears' third album, with Timberlake contributing background vocals.

In 2002, Britney Spears and Justin Timberlake made a joint appearance on the Grammys red carpet, which was one of their final public appearances as a couple before parting ways.

During the ceremony, Spears had the honor of presenting the award for the best pop performance by a group or duo. Interestingly, Timberlake was a nominee in that category with *NSYNC, but their moment to share a Grammy was missed, as Spears didn’t win in that category.

Their highly publicized breakup in 2002 marked a turning point in their relationship. Timberlake released "Cry Me a River," a song with lyrics that seemed to allude to their romance. The accompanying music video featured a Spears look-alike, sparking widespread media attention.

Spears expressed her disappointment with Timberlake's approach to the breakup in an interview, labeling him as "exploitative." She believed that their private matters should have remained sacred.

After Spears and Timberlake parted ways, they both entered new relationships. Spears married Kevin Federline in September 2004, while Timberlake began dating actress Cameron Diaz in 2003.

In 2006, Timberlake admitted to being infatuated with Spears when they first met, but he characterized their past relationship as having a "high school" quality and becoming a distant memory.

On April 15, 2020, Britney Spears posted an Instagram video of herself dancing to Timberlake's song "Filthy." In her caption, she praised Timberlake's musical talent and acknowledged their widely publicized breakup.

In response, Timberlake commented on the post using a series of emojis, indicating his amusement and appreciation for her gesture.

Years later, Justin Timberlake publicly apologized to Britney Spears for his past actions and behavior during their breakup through a lengthy Instagram post. He expressed his support for her during her conservatorship hearing, acknowledging the injustice of her situation and emphasizing that no woman should be restricted from making decisions about her own body.

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In her 2023 memoir, "The Woman in Me," Britney Spears disclosed a deeply personal detail about her relationship with Timberlake. She revealed that she had become pregnant with his child during their time together but had an abortion. Timberlake, at the time, was not ready to become a father, causing strain in their relationship.