Britney Spears and Justin Timberlake's Relationship Timeline

December 1992: Spears and Timberlake Meet on The All-New "Mickey Mouse Club"

The future superstars first met in the early '90s when they were both cast on the revival of the popular kids' variety show "The Mickey Mouse Club." Timberlake left the show in 1994, when he recruited fellow Mouseketeer JC Chasez to start a boy band, which soon became *NSYNC. Spears, on the other hand, stayed with the show until its 1996 cancellation.

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1999: Spears and Timberlake's Relationship Goes Public

Image Source: Getty / Kevin Mazur

The former costars reunited a few years after the end of the show, and they were publicly dating by early 1999. By 2001, they were living together when not on tour, according to an interview in The Observer, and Spears opened up about the relationship.

"When people [in the public] get too personal, it bothers me. But 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. He's everything," she mused. "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."

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January 2001: Spears and Timberlake's Iconic Denim-on-Denim Moment

Image Source: Getty / Jeffrey Mayer

If there's a defining image of the couple's relationship, it's this: their matching, head-to-toe denim outfits at the 2001 American Music Awards.

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February 2001: Spears and Timberlake Perform Together at the Super Bowl

Image Source: Getty / Jeff Kravitz

At the halftime show for Super Bowl XXXV, Spears and Timberlake performed together as part of the MTV-produced show. The performance included Aerosmith, *NSYNC, Spears, Mary J. Blige, Nelly, and Tremors featuring The Earthquake Horns.

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March 2002: Spears and Timberlake Break Up

Image Source: Getty / Jeff Kravitz

In 2002, the couple abruptly split, and, pretty quickly, Timberlake snagged the role of victim, going on interview circuits and talking about being cheated on while also slut-shaming Spears. Some of these clips made it into the "Framing Britney Spears" documentary.

"He has gone on television and pretty much said you broke his heart," Diane Sawyer tells Spears in one interview clip. "You did something that caused him so much pain, so much suffering — what did you do?"

Timberlake also bragged about sleeping with Spears in several different interviews — occasionally alluding to graphic details — and, during one Barbara Walters interview, outright laughed when Walters asked if Spears had kept her promise to wait until marriage to have sex.

"The way that people treated her, to be very high school about it, was like she was the school slut and he was the quarterback," The New York Times critic at large Wesley Morris says in the documentary.

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December 2002: Timberlake Releases "Cry Me a River"

Timberlake's music video for "Cry Me a River" is, infamously, all about his breakup with Spears — it even features a Spears look-alike. "You don't have to say, what you did / I already know, I found out from him / Now there's just no chance / With you and me / There'll never be," goes one verse, which reportedly alludes to Timberlake finding out that Spears was cheating on him with a choreographer they both knew.

The people interviewed in "Framing Britney Spears" suggest that the video, as well as the accompanying promotional tour, was a way to weaponize the breakup for Timberlake's benefit, painting him as the heartbroken guy and Spears as an unfaithful villain.

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November 2003: Spears Releases "Everytime"

On her album "In the Zone," Spears released "Everytime," widely considered her "reply" to Timberlake's music and their breakup. It reads like an apology: "I may have made it rain / Please, forgive me / My weakness caused you pain / And this song's my sorry," goes one verse.

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September 2006: Timberlake Releases "What Goes Around . . . Comes Around"

On his 2006 album "FutureSex/LoveSounds," Timberlake included a diss track, "What Goes Around . . . Comes Around." The release coincided with the start of Spears's personal struggles: her second pregnancy, several paparazzi incidents, and the end of her marriage to Kevin Federline.

During his press tour for the album, Timberlake again blamed Spears for the post-breakup media buzz, while confirming that "Cry Me a River" was about her in GQ (per CBS News). "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," he said.

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February 2021: Timberlake Addresses "Framing Britney Spears"

Image Source: Getty / Jeff Kravitz

Timberlake responded to the documentary with an apology and also shared his regrets about what happened with Janet Jackson at the 2004 Super Bowl. "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. I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism," he wrote on Instagram. "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 . . . I know this apology is a first step and doesn't absolve the past. I want to take accountability for my own missteps in all of this as well as be part of a world that uplifts and supports. I care deeply about the wellbeing of the people I love and have loved. I can do better and I will do better."

In June 2021, Timberlake shared support for Spears after she spoke out about her conservatorship for the first time. "After what we saw today, we should all be supporting Britney at this time," he tweeted. "Regardless of our past, good and bad, and no matter how long ago it was . . . what's happening to her is just not right. No woman should ever be restricted from making decisions about her own body. No one should EVER be held against their will . . . or ever have to ask permission to access everything they've worked so hard for."

He continued, "Jess and I send our love, and our absolute support to Britney during this time. We hope the courts, and her family make this right and let her live however she wants to live."

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October 2023: Spears Reveals She Had an Abortion While Dating Timberlake

Image Source: Getty / Jeff Kravitz

In an excerpt from her memoir shared with People on Oct. 17, Spears shared that while she and Timberlake were dating, she became pregnant and ultimately had an abortion. "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. This would just be much earlier than I'd anticipated," she wrote. "But Justin definitely wasn't happy about the pregnancy. 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 went on to describe the abortion as "one of the most agonizing things I have ever experienced in my life."

Reps for Timberlake did not immediately respond to POPSUGAR's request for comment.

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