Inside Britney Spears and Justin Timberlake’s relationship

In the wake of The Woman in Me, we delve deeper.
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They were one of the 2000s’ most iconic couples but in the wake of the Framing Britney Spears documentary by the New York Times, fans began questioning the pop star’s relationship with Justin Timberlake.

Now, as Britney releases her tell all memoir, fan are getting an inside look into the highly publicised relationship. 

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Britney and Justin dated for three years and announced their split in 2002, around the time when Justin was branching out as a solo artist.

At the time, the former NSYNC boyband member was portrayed as a sensitive star who’d had his heart broken by Britney whilst she was chastised for her “wild nights” and apparent “betrayal” of her ex.

So how did all this drama start? We take a deep dive look into the relationship that ended nearly 20 years ago that is once again making headlines.

Justin and Britney first met as children on The Mickey Mouse Club. (Credit: Getty)

Though the couple first met on The Mickey Mouse Club in 1992, Britney and Justin didn’t go public with their relationship until 1999.

“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,” Britney told The Observer.

The pair went on to perform at the 2001 Super Bowl Halftime Show together and rock those iconic denim on denim outfits at the American Music Awards that same year.

However after they ended things in 2002, things turned ugly.

An iconic look. (Credit: Getty)

In the wake of their split, Justin appeared on various televised interviews to promote his new solo career, but ended up discussing his ex with very personal details.

His now infamous interview with Barbara Walters featured him denying that any songs on his new album were about Britney, but he then played a song called Horrible Woman that featured lyrics including: “I thought our love was so strong / I guess I was dead wrong / But to look at it positively, hey girl / At least you gave me another song about a horrible woman.”

Justin then outright laughed when asked if Britney had kept her promise to wait until marriage to have sex.

Meanwhile when Diane interviewed Britney on the same topic, the TV reporter asked: “He has gone on television and pretty much said you broke his heart. You did something that caused him so much pain, so much suffering — what did you do?”

Britney is currently dating boyfriend Sam Asghari. (Credit: Instagram)

2002 saw the release of Justin’s hit Cry Me A River that reportedly alludes to Justin finding out that Britney was cheating on him with a choreographer they both knew.

The music video even features a woman who looks remarkably like his ex and the Framing Britney Spears interviewees suggest that the video and the accompanying promotional tour, was a way to market Justin as the innocent, heartbroken guy and Britney as an unfaithful villain.

A year later, Britney released her ballad Everytime which is thought to be a response 

“I may have made it rain / Please, forgive me / My weakness caused you pain / And this song’s my sorry,” the lyrics of one verse say.

Then in 2006, Justin released another revenge song What Goes Around . . . Comes Around that coincided with the start of Britney’s personal struggles including several clashes with the paparazzi and the end of her marriage to Kevin Federline.

During his press tour for the FutureSex/LoveSounds album, Justin confirmed that Cry Me a River was about her in GQ, explaining: “I felt like she had a couple of opportunities to just sort of stick up for me, and she didn’t. Which is fine. But at that time, you know, I fought back, and that’s the way I fought back. I used my mind. I came up with a song.”

Justin Timberlake is now married to actress Jessica Biel. (Credit: Instagram)

Following the release of the New York Times‘ explosive documentary in 2021 Justin issued a personal apology to Britney and Janet Jackson, the latter of whom was slammed after her 2004 Super Bowl set with Justin when she suffered a wardrobe malfunction whilst her co-performer had seemingly no similar repercussions.

“I’ve seen the messages, tags, comments and concerns and I want to respond. 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,” he wrote on Instagram.

“I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism,” Timberlake continued. “I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed.”

“I also feel compelled to respond, in part, because everyone involved deserves better and most importantly, because this is a larger conversation that I wholeheartedly want to be part of and grow from … “

Britney Spears memoir

In October 2023 Britney released her own memoir The Woman in Me which shed light on the purported cruelty she endured during the unique conservatorship she was subjected to from 2008 to 2021, as well as her reported abortion while in a relationship with Justin Timberlake.

“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,” she wrote in an excerpt published by People.

“He said we weren’t ready to have a baby in our lives, that we were way too young.”

“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.”

Grab Britney’s memoir, here.

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