A Look Back At Britney & Justin's Rollercoaster Relationship

Spears and Timberlake first met while filming The Mickey Mouse Club in 1992, but they didn’t actually confirm their romance until 1999. Their relationship was a long time coming, though, especially if you ask JT.

Per Us Weekly, he told GQ in 2006, “I was in love with her from the start. I was infatuated with her from the moment I saw her.” Nothing like falling for your childhood crush.

In what might be the most iconic JT-Britney moment, the two wore matching all-denim outfits to the American Music Awards in 2001. Although this photo opp has become the source of infinite Halloween costume inspo for couples everywhere, Timberlake kind of wishes everyone could forget about it.

“I confess that there was maybe a period in the '90s where I could skip over some of the outfits that were public, but the internet will never,” he told The Hollywood Reporter in February 2021.

During an interview with The Guardian in 2001, Spears said that their relationship was getting very serious, explaining that Timberlake “lives at her house with her when he's in LA.”

She added at the time, “I'm not ashamed at all to say that I love him from the bottom of my heart. As far as love is concerned, with him, too much is not enough.”

Spears and Timberlake shocked fans when they broke up in March 2002, and they were interviewed about it repeatedly in the months following.

In November 2002, Timberlake revealed some details of their split to Barbara Walters. "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 said, per Us Weekly. He also “promised her that [he] wouldn't say specifically why [they] broke up." He also laughed when Walters asked about their sex life.

Despite Timberlake's words, the breakup was tough for Spears to swallow. In December 2021, the “Toxic” singer opened up about her post-breakup emotions in a since-deleted Instagram. “Something I never shared when I had that big breakup years ago was that I couldn't talk afterwards. I never spoke to anyone for a very long time,” she wrote.

During an interview with The Star & Buc Wild Morning Show, Timberlake was asked, “Did you f*ck Britney Spears?” It was a loaded question, considering how publicly Spears had spoken about wanting to wait to have sex until after marriage. Still, that didn’t stop Timberlake from answering (even if it should have). “Oh man,” he responded. “OK, I did it!” (Gross.)

Despite what Timberlake said to Walters about staying mum on the reasons behind their split, he didn’t keep to his word. That same month, he released his “Cry Me A River” music video, which told a very different story of their breakup and pointed the blame squarely in Spears’ direction. To make the message crystal-clear, he cast a Spears lookalike to play the role of his cheating ex-girlfriend.

In an interview with W Magazine, Spears responded to Timberlake’s comments — and she was understandably not happy about them. “I’ve only slept with one person my whole life,” she explained at the time, per CBS News, adding that she did wait ”two years into [her] relationship with Justin” to have sex.

She explained her disappointment with Timberlake’s comments: “I thought he was the one. But I was wrong! I didn’t think he was gonna go on Barbara Walters and sell me out.”

Following the Framing Britney documentary, which highlighted Timberlake’s unflattering comments, the actor received plenty of feedback. On Feb. 12, he responded to the criticism by finally apologizing to Spears, as well as Janet Jackson.

“I've seen the messages, tags, comments, and concerns and I want to respond,” he wrote on Instagram. “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. I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism. 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.”

Spears didn’t respond to Timberlake’s apology — at least, not publicly. But she did reference her ex in an Instagram caption in August 2021, writing, “As JT would say ... haters gonna say it’s fake !!!!!” The picture was a photo of a large cat, though, so there didn’t seem to be any hidden meaning to her post.

Spears’ memoir, out Oct. 24, is reportedly full of surprising revelations about her and Timberlake’s three-year relationship. According to her, she and Timberlake both cheated on each other throughout the course of their relationship. Per Us Weekly, she cheated once with choreographer Wade Robson, and Timberlake cheated “a couple of times” with different women.

Spears also shared that she had an abortion while dating Timberlake. “It was a surprise, but for me, it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day,” she wrote about her accidental pregnancy in an excerpt published by People. “This would just be much earlier than I’d anticipated.”

Timberlake was less “happy” about the pregnancy, according to Spears, prompting her to get an abortion. “He said we weren’t ready to have a baby in our lives, that we were way too young ... 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 wrote.