Double denim to break-up text: Justin Timberlake and Britney Spears’ relationship timeline

Britney Spears and Justin Timberlake were essentially the it couple of the ’90s. But, after years of cheating speculation from fans and tabloids, recent excerpts leaked from her upcoming memoir The Woman in Me, make it clear their relationship may not have been as fun as it looked from the outside.

So, in case you’re confused by all of the relationship revelations coming out online ahead of Britney’s book’s release date, here’s everything you need to know about the timeline of her and Justin’s time together, including all the infidelity allegations and how she claims their break up really went down:

Britney and Justin meet on set of the Micky Mouse Club when she’s 11-years-old

Britney and Justin were both stars on the kids’ variety show The Mickey Mouse Club, which is where they first got to know each other in 1992. Justin left the show in 1994 and started *NSYNC but Britney stayed on the show until it was cancelled in 1996: “The Mouseketeers quickly split into our own cliques, divided by the dressing rooms that we shared: Christina Aguilera and I were the younger kids, and we shared a dressing room. We looked up to the older kids — Keri Russell, Ryan Gosling, and Tony Lucca, who I thought was so handsome,” Britney reportedly writes in her memoir of the job. “And I quickly connected with a boy named Justin Timberlake.”

They go public with their relationship seven years after meeting on MMC

Credit: MediaPunch/Shutterstock

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Seven years after they first met on The Micky Mouse Club, Britney and Justin were publicly dating and going to showbiz events together. “I love him from the bottom of my heart. As far as love is concerned, with him, too much is not enough. He’s everything,” Britney told The Observer. “It is a deeper love now than when I was younger. Like, we’ve gone through so much together and we’ve known each other since we were 12 years old. We know each other inside and out.”

Cheating rumours surface about Justin and another famous singer in London

Yikes! Anyway, let’s not forget Justin chested on Britney first with Nicole Appleton from the band All Saints. https://t.co/tOTXP141bc pic.twitter.com/EOPhuEzwKO

— Fan Account (@breatheonmiley) November 24, 2019

Britney claims in her memoir that Justin Timberlake cheated on her with “another celebrity”. She doesn’t name the woman but there has long been speculation that in 2000 Justin had a relationship with Nicole Appleton – a singer from the girl band All Saints. Justin was famously seen with Nicole going back to his London hotel after a night out . But the rumour has never been substantiated and neither Justin nor Nicole have ever commented on the claims.

Britney cheats on Justin by kissing ‘her choreographer Wade Robson’

According to The New York Times, Britney admits to cheating on Justin during their relationship in her memoir with her Oops…I Did It Again and I’m A Slave 4 U choreographer, Wade Robson: “We were out one night and we went to a Spanish bar. We danced and danced. I made out with him that night,” ” Britney writes of the infidelity. However, she claims apart from that “one exception”, she never cheated on Justin and told him about the kiss with Wade, which they were able to move on from and continue their relationship.

Britney ‘has an abortion’ and Justin ‘plays guitar’ to comfort her as she ‘sobs’

oh so britney spears’ everytime wasn’t about justin timberlake but it was about the baby?!
pic.twitter.com/hfS24WA2WX

— 2000s (@PopCulture2000s) October 17, 2023

Britney reveals in her memoir she had an abortion in 2000 while she dating Justin: “It was a surprise, but for me, it wasn’t a tragedy,” Britney wrote of her pregnancy in an excerpt obtained by People. “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.

“He said we weren’t ready to have a baby in our lives, that we were way too young,” she writes. “I’m sure people will hate me for this, but I agreed not to have the baby. 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,” she said, adding it was “one of the most agonizing things I have ever experienced in my life.” Fans now think the ordeal inspired her song Everytime, as a baby is born during the music video.

According to Us Weekly, Justin attempted to console Britney, who was “crying and sobbing” on the bathroom floor, by playing his guitar because he “thought maybe music would help.”

Justin ends their three year relationship by sending Britney a ‘two word’ text message

Credit: Matt Baron/BEI/Shutterstock

In 2002, Britney was filming her music video for Overprotected: The Dark Child and the video’s director, Chris Applebaum, has claimed to PageSix that Justin ended his three year relationship with Britney during that shoot – with a two word text message.

According to Chris, Britney went missing from the set while they were filming and when he went to look for her, he found her sat on the floor, crying, in her trailer because Justin had sent her a message saying: “It’s over!!!”. And, after their relationship ended, Justin spoke extensively about Britney in the media, bragging (in graphic detail) about the times he’d slept with her.

Justin releases Cry Me A River and uses a Britney lookalike in the music video

In 2002, Justin released his song Cry Me A River, which famously was about Britney and her kissing her dance choreographer while they were in a relationship. In the documentary Framing Britney Spears, interviewees suggest this was a way to paint Justin as the victim. Fans have also pointed out the move was particuarly harsh in the wake of her pregnancy. “Justin Timberlake releasing ‘Cry me a River’ while Britney was grieving the loss of the baby he forced her to abort is really sick if you think about it,” one wrote on Twitter. “And then putting her lookalike in the video?” 

Recommended stories by this writer:

• Justin Timberlake to Colin Farrell: Every big revelation from Britney Spears’ book so far 

• Why Britney Spears fans think Everytime is about her abortion with Justin Timberlake

• The definitive ranking of Britney Spears music videos, based on how iconic they are

Featured image credit via MediaPunch/Shutterstock