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Justin Timberlake and Britney Spears were the “it couple” of the early 2000s. After coming together on *NSYNC’s concert tour in 1998, the pair began dating and were together for three years before calling it quits in 2002.

Though they fell head over heels for each other as young adults, it turns out that Timberlake was smitten with Spears long before they became an official couple.

Justin Timberlake and Britney Spears
Justin Timberlake and Britney Spears | Dave Hogan/Getty Images

Britney Spears and Justin Timberlake go way back

Spears and Timberlake met back in 1992 when they were both cast on Disney’s The All-New Mickey Mouse Club (also known to fans as MMC) alongside future stars like Christina Aguilera and Ryan Gosling.

Though they didn’t start dating until years later, Timberlake told GQ magazine in 2006 that he fell head over heels for Spears when they met as Mouseketeers on the Disney Channel show.

“I was in love with her from the start,” he said, per KLTV. “I was infatuated with her from the moment I saw her.”

After the show was canceled in 1996, both Timberlake and Spears went their separate ways to find stardom in the music industry. While Timberlake formed the all-male singing group *NSYNC with fellow Mouseketeer JC Chasez, Spears embarked on a solo career.

In 1998, the “Oops!… I Did It Again” singer reconnected with Timberlake when she was brought on as the opening act for *NSYNC’s second concert tour.

Britney Spears and *NSYNC
Britney Spears and *NSYNC | Kevin Mazur Archive/WireImage

In 2000, the pop princess confirmed she and Timberlake were dating following a year of media speculation.

After that, the singers’ relationship was on full display as they made plenty of memorable appearances together, including the time they wore matching denim outfits to the 2001 American Music Awards. The duo even did an adorable photoshoot together with Hello! Magazine.

Unfortunately, their relationship didn’t last as they called it quits in 2002.

Why did Britney Spears and Justin Timberlake break up?

After news of their breakup made headlines, many began to speculate why Timberlake and Spears called it quits.

While it was rumored the pair broke up because the “Everytime” singer had cheated on JT (his “Cry Me A River” music video only fueled this speculation), Spears later claimed (per Daily Mail) that she and Timberlake broke up because they both had different life goals.

Though neither of them went into detail about why they called it quits, Timberlake told Barbara Walter during an interview that he will always love Spears and that he will never tell the media what really went down between them.

Justin Timberlake and Britney Spears
Justin Timberlake and Britney Spears | Ron Galella Collection via Getty Images
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“I remember when we decided we were going to go our separate ways, we sat down and I said to her, ‘If there’s ever a moment where you ever need me, you can rest assured that I will be there, because I love you as a person and I will always love you,'” he told Walters, per Bustle. “But I also said, ‘Look, no matter what we say at this point people are going to speculate things, and I could really get myself in horrible position if I was to say something and somebody misinterpreted, because that happens all the time.’ And I promised her that I wouldn’t say specifically why we broke up.”

Britney Spears is still a fan of Justin Timberlake

Though both pop stars were heartbroken after calling it quits, they have since moved on from that point in their lives.

Today, Timberlake is still a successful recording artist and is married to 7th Heaven actor Jessica Biel. Together, they have two sons: Silas Randall (born April 2015) and Phineas (born July 2020). 

Spears, on the other hand, fell on a few hard times over the years but has always come out on the other side stronger. Though she was the star of her own Las Vegas residency, she announced an “indefinite work hiatus” in January 2019 to focus on her family.

Since then, she’s been spending time at home with her two kids Sean and Jayden, who she shares with ex-husband Kevin Federline, and her boyfriend of four years, Sam Asghari.

As for Spears and Timberlake’s relationship, it appears they continue to have mutual respect for each other.

In 2018, Spears called her former beau a “genius” when she posted an Instagram video of her jamming to his track “Filthy.” She captioned the clip, “I know we had one of the world’s biggest breakups 20 years ago …… but hey the man is a genius !!!! Great song JT.”

Timberlake then proved there’s no bad blood between them by commenting on the video with raised hands and laughing-crying emojis.

Recently, Spears shared another Instagram video of her dancing to JT’s song “Holy Grail,” which instantly got people talking. Though Timberlake hasn’t commented on the post yet, we wouldn’t be surprised if he gave the video his stamp of approval just like he did a few years ago!