A Comprehensive Timeline Of Britney Spears And Justin Timberlake’s Relationship

“I was in love with her from the start.”

Images via Instagram, @britneyspears @justintimberlake

Britney Spears and Justin Timberlake’s love story has led to drama, controversy, and some of the world’s most iconic moments in fashion and pop culture.

The pop prince and princess found love from a young age, and the tale of their affair was dominant right through the ’90s to the 2000s.

It’s been over twenty years since their earth-shattering breakup, but the release of Britney’s brand new memoir The Woman In Me has brought their relationship back into the limelight.

Now, people are looking back on the tumultuous couple and wondering how it all went down.

We did some digging to create a timeline of everything that happened between Justin Timberlake and Britney Spears – let’s get into it!

December 1992 – Britney and Justin Meet on the “All-New Mickey Mouse Club.”

In the early 90s, boy meets girl.

Britney and Justin were just 11 when they first met! They were cast as “Mouseketeers” in the “All New Mickey Mouse Club” on Disney.

The TV show was the home of young performers in Hollywood who would later go on to become some of the world’s greatest stars, including a mini Ryan Gosling and baby Christina Aguilera.

Timberlake had allegedly given Spears her first kiss whilst filming a scene of Truth or Dare for the show, as recently revealed in Britney’s memoir. Little did the future pop stars know what was to come!

In a 2006 interview with GQ Magazine, Justin recalled being infatuated with Britney from the very first moment they met, “I was in love with her from the start.”

November 1998 – Britney and Justin Reunite


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Shortly after his Disney days, Timberlake would go on to form the iconic boy band *NSYNC, alongside JC Chasez, Chris Kirkpatrick, Joey Fatone and Lance Bass.

Following Britney’s rise to stardom after the release of her debut single “…Baby One More Time”, the young lovers, now teens, would reconnect on the *NSYNC tour.

Spears performed as the opening act for the band from late 1988 to early 1999. Perhaps this is when their love story officially kicked off!

September 2000 – Britney and Justin Go Public


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At the 2000 MTV VMAs, Britney and Justin made their first public appearance, signalling to fans that they were official.

Despite not walking the red carpet together, the pair were seen cosying up to one another in the audience and posed together for pictures.

January 2001 – The Denim on Denim Duo

Is this the defining moment of their relationship?

Heads were turned at the 2001 American Music Awards when Brit and Justin walked the red carpet in matching denim-on-denim fits.

This legendary look would go on to inspire many a fancy dress night, where fans would channel their inner Britney and Justin.

January 2001 –  Super Bowl Performance

A true career milestone.

Imagine performing alongside Aerosmith, Mary J. Blige, Nelly and *NSYNC, at the Super Bowl of all things. Yeah, they did that!

Britney and Justin shared this famous moment whilst performing “Walk This Way”, on the stage of the Super Bowl XXXV Half-Time Show. Sensational!

February 2002 – Nearing The End


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During the last days of their relationship, Britney and Justin made one of their final appearances as a couple on the red carpet of Clive Davis’ Pre Grammy Party.

March 2002 – Brit and Justin Break Up


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In a March 2002 interview on the Big Breakfast talk show, Britney revealed that she was no longer in a relationship.

“I’m single…right now.”

Justin was quick to tell the media that he was the victim in the break-up, revealing in a number of interviews that he had been cheated on by Britney.

He told People Magazine at the time about his “broken heart”, saying “It hurts too bad. 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.”


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But what really happened?

In her memoir, “The Woman In Me”, Britney reveals that it was actually Justin who initiated the breakup, writing that he wanted to use the heartbreak as “ammunition for his record.” She also reveals that while yes, she did cheat on Justin once (kissing her backup dancer Wayne Robson while they were together), Justin also cheated on her – numerous times.

Britney details how Justin broke up with her in a two-word text, whilst she was shooting for the music video for the remix of her song Overprotected, before later officially dissolving the love affair with a handwritten letter.

At this point, what is love?

October 2002 – Cry Me A River


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And so, the breakup songs begin.

In October 2002, Timberlake released his single Cry Me a River, where he appeared to address what had happened with Britney.

Soon after he released the music video for the song, which featured a Britney Spears lookalike, and you best believe the cheating rumours were fuelled.

The lyrics  suggest that it was Britney who left Justin and that he knows what she was disloyal; “You don’t have to say, what you did/ I already know, I found out from him/ Why did you leave me all alone.”


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In The Woman In Me, Britney explains how she was left feeling severely scrutinised by her fans and the media over the video.

“I was described as a harlot who’d broken the heart of America’s golden boy.” She continues to recall the times that Justin had been disloyal to her but she stayed with him, writing, “I was so infatuated and so in love, I let it go.”

Honestly, the tune is a banger, but seriously Justin…cry us a river!

2004 – Britney’s Break Up Song

In May 2004, Britney released a heartbreak track and video of her own, Everytime, which led to a lot of speculation regarding the pair’s split.

The song lyrics state, “I may have made it rain/ Please, forgive me/ My weakness caused you pain/ And this song’s my sorry.”

The video featured a scene of Spears bleeding blood in a bath and another of her in a maternity ward.

The meaning behind this song is now being perceived differently than it was at the time, following a shocking revelation in Britney’s recent memoir.

October 17. 2023 – Britney Reveals A Secret


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In her new book, Britney dropped many surprising revelations about her past. One which shocked fans the most, pertained to her relationship with Justin.

The pop star disclosed that in the midst of their relationship, Britney became pregnant and consequently had an abortion.

Britney described feeling surprised, although not disappointed about the pregnancy, whilst Justin was not happy. According to the memoir, Justin believed that they weren’t yet ready to have a baby in their lives and told her that they were far too young.


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Britney admitted, “If it had been left up to me alone, I never would have done it.” She writes that the experience is “one of the most agonising things I have ever experienced in my life.”

The revelation made many view her music video Everytime differently, with some believing that the song addresses the abortion, not her relationship with Justin.

Though Britney’s book was only released last week, many are waiting for Justin to release some comment on what she discusses.

As of now, he hasn’t responded to any claims made in the memoir.


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However, it doesn’t seem as though Britney wants there to be any wounds re-opened. Taking to her Instagram to address the uproar over how she was treated by the people in her life, Britney asked people not to “harp on” about what she has written.

“My book’s purpose was not to offend anyone by any means!!! That was me then…that is in the past!!!…Most of the book is from 20 years ago…I have moved on and it’s a beautiful clean slate from here!!!”

Words by Shauna Whyte