Britney Spears And Justin Timberlake's Complete Relationship Timeline

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If there's one celebrity romance the world just can't seem to get over, it's Britney Spears and Justin Timberlake's. The two were pretty much the darling couple of the world back in the late 1990s and early 2000s, bringing us some of the most iconic couple costumes in history (paging that infamous double denim look). But despite the couple only lasting around three years, they've been asked about one another more times than we can physically count in the wake of their break-up — but it's not just journalists and fans who can't seem to stop speaking about Spimberlake (we're just going try out this new couple name here).

As you'll come to see, Timberlake and Spears have both been pretty vocal about each other on multiple occasions since they called it quits all the way back in 2002 (yes, it really was that long ago). Sometimes it's been good and sometimes, well, it's been not so good. So buckle up and grab a scrunchie and a copy of Tiger Beat, because we're taking a look back at how these two left a schoolgirl costume and bleach blond curly hair imprinted on America's hearts — and everything that's happened between them since.

1993: Britney Spears and Justin Timberlake meet on 'The All New Mickey Mouse Club'

Britney Spears and Justin Timberlake's romance started off in a way usually only rom-com writers can muster. As children! The adorable beginning dates back to around 1993 when the two appeared on "The All-New Mickey Mouse Club" together, alongside the likes of Christina Aguilera and Ryan Gosling. Of course, they were just kids at the time, so there was nothing romantical here ("Obviously, the feelings of love weren't as developed as they possibly could be," Timberlake told ABC News in 2002 of those early days). Even so, it's where things started to blossom for America's one-time golden couple. 

"I was in love with her from the start. I was infatuated with her from the moment I saw her," he admitted to GQ in 2006 (via CBS News), having previously revealed that he gave Spears her very first kiss. Spears expanded on that sweet moment in her 2023 memoir, "The Woman in Me," revealing that it happened during a popular slumber party game at an overnight get together between the Mousketeers cast. 

"[Once] at a sleepover, we played Truth or Dare, and someone dared Justin to kiss me," Spears wrote (via People). She added another fun anecdote, noting the music that played at the time was also significant, "A Janet Jackson song was playing in the background as he leaned in and kissed me." Timberlake would famously go on to perform at the 2004 Super Bowl with Jackson, a halftime show that would be shrouded in controversy.

1999: Spears and Timberlake make their picture-perfect romance official

Though they went their separate ways for a little while after their Disney days, Britney Spears and Justin Timberlake found their way back together as they both embarked on pop superstardom. Of course, Spears went solo and Timberlake joined *NSYNC, and the childhood friends had the world in a frenzy in 1999 when they officially confirmed they were dating.

On "Rich And Famous," Spears later remembered of reuniting with Timberlake: "He definitely asked me out. We were doing a radio show, and this was before '...Baby One More Time' came out ... He knocks on the door and he was like, 'Can I see Britney?' And [my assistant] Felicia [Culotta] didn't know who he was and she was like, 'No. Who are you?' And I was like, 'No! It's Justin!'"

Things went well for a fairly long time between the two as well, with Spears sharing in September 2001 that Timberlake was living with her when he was in Los Angeles. He was also imparting wisdom, teaching Spears how to play the guitar. "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 gushed to The Guardian. Aww!

2000: Britney became pregnant with Justin's child

Early in their relationship, Britney Spears became pregnant with Justin Timberlake's baby. This bombshell was dropped within the pages of Spears's memoir, "The Woman in Me," released in October 2023. In the book, Spears revealed the secret she had been keeping for over two decades; that she went on to have an abortion after some urging from 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. This would just be much earlier than I'd anticipated," Spears wrote (via People). "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."

Both musicians were at the height of their careers at the time, and Timberlake had concerns a baby would derail their success. Despite going through with the abortion, the pop star maintained that it wasn't her idea or preference, sharing, "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 also noted that she still struggled with the decision, writing, "To this day, it's one of the most agonizing things I have ever experienced in my life."

2001: Britney and Justin's iconic denim-on-denim moment

Who could forget one of the most iconic fashion moments in red carpet history? In the midst of their romance back in 2001, Britney Spears and Justin Timberlake arrived at the American Music Awards rocking matching denim ensembles. Over two decades later, in Spears's 2023 memoir, "The Woman in Me," (via People) the legend revealed exactly whose idea it was to match. 

The "Toxic" singer revealed that it was originally her call to don denim, sharing that she told Timberlake, "We should match! Let's do denim-on-denim!" Despite coming up with the plan, Spears wrote that she didn't think anyone would take her seriously, writing, "At first, honestly, I thought it was a joke. I didn't think my stylist was going to do it, and I never thought Justin was going to do it with me. But they both went all in." 

The rest is fashion history! Spears reminisced about the moment she saw her boyfriend's look, sharing, "When he put it on, I thought, 'Whoa! I guess we're really doing this!'" And though she realizes the looks were "tacky," she echoed something Timberlake himself said about the ensembles. Back in March 2020, Timberlake appeared on former bandmate Lance Bass's podcast, "The Lance Bass Show," and stated, "You do a lot of things when you're young and in love." Spears mentioned that exact quote from her ex in her memoir, writing, "And that's exactly right. We were giddy, and those outfits reflected that." 

2002: Justin broke up with Britney via text

Despite knowing each other since they were kids and dating for nearly three years, when it came time to end things Justin Timberlake broke up with Britney Spears via a text message. The shockingly brutal way Timberlake called it quits was revealed in Spears's memoir, "The Woman in Me," with the pop star sharing she was on the set of her music video for "Overprotected" when she received the message.

The music video's director, Chris Applebaum, spoke to Page Six about that fateful day, explaining that Britney disappeared from set late during the second day of filming. Upon finding her in her trailer, Applebaum shared that she was sitting on the floor crying when she told him, "I can't believe it. Look it. This happened." On Britney's Motorola flip phone was a text message that Applebaum recalled read, "It's over!!!"

Spears elaborated on the painful moment in her memoir (via E! News), sharing, "After seeing the message as I sat in my trailer in between takes. I had to go back out and dance." The breakup left her reeling, with the singer reminiscing about the time by writing, "For as much as Justin hurt me, there was a huge foundation of love and when he left me, I was devastated. When I say devastated, I mean I could barely speak for months. Whenever anyone asked me about him, all I could I do is cry. I don't know if I was clinically in shock, but it felt that way."

2002: News of their split shocked the world

Despite everything seeming picture-perfect between Britney Spears and Justin Timberlake to the public, the two split suddenly in March 2002 — shortly after Spears gushed on "The Oprah Winfrey Show" (via Billboard) that Timberlake had given her a ring (not of the engagement kind, though). Spears confirmed the shocking news in a press conference (via CNN), saying, "I would not say I was in an intense relationship with anyone at the moment," before stating during an appearance on Britain's "Big Breakfast," "I'm single right now."

Really cementing that America's favorite couple was no more, Spears attended the London premiere of her movie, "Crossroads," sans the pinky ring Timberlake had given her and without her (former) man by her side. As for what Timberlake was up to? Well, CNN reported he was spotted back in the U.S. with another woman.

Timberlake later spoke with People about the difficulty of the split, admitting, "You get to a point where you're crying yourself to sleep every night. I feel like I'm in the middle of a soap opera. I honestly know what it's like to have a broken heart ... I love Britney, and I'll always love her." As for a reconciliation? Timberlake admitted to ABC News that he wasn't sure if they'd ever reunite, but said, "We're not perfect. I don't judge anybody. It's just young love. ... It was a very intense relationship, that's for sure."

2002: Timberlake released 'Cry Me a River' with a Spears lookalike

There wasn't much time for the dust to settle on Britney Spears and Justin Timberlake's split before they were exchanging words in song, as it's no secret Timberlake's huge 2002 hit "Cry Me a River" is thought to be about the split. The lyrics hint that Spears may have been unfaithful, while the music video even features a Spears lookalike.

Timberlake has spoken out about the speculation too, telling GQ (via CBS News) in 2016, "I felt like [Spears] had a couple of opportunities to just sort of stick up for me, and she didn't. Which is fine. But at that time I fought back, and that's the way I fought back. I used my mind. I came up with a song." He revealed in his 2018 book, "Hindsight: And All the Things I Can't See in Front of Me" (via People) that he penned the track in just two hours.

While she admitted to sharing one kiss with choreographer Wade Robson, Spears opened up further about her thoughts on the video in her 2023 memoir "The Woman in Me" (via Entertainment Weekly), revealing that the cheating went both ways. "In the news media, I was described as a harlot who'd broken the heart of America's golden boy ... May I just say that on his explosive album and in all the press that surrounded it, Justin neglected to mention the several times he'd cheated on me?" Spears wrote.

2003: Britney released her own breakup tune, 'Everytime'

While Justin Timberlake made waves with his breakup tune "Cry Me a River" in 2002, Spears wasted no time penning her own splitting anthem ... though her version ended up being much more emotional. In a 2003 interview with Hip Online, Spears shared her intention behind the song, stating, "It's kind of personal in a weird way. I just think the song — it's one of the songs that when you hear, it's like the kind of song when you go to heaven. It kind of takes you away."

"Everytime" was seen in a new light following the 2023 release of Spears's memoir, "The Woman in Me." The singer dropped the bombshell that she had an abortion during her time with Timberlake within the pages of the book, causing eagle-eyed fans to remember the song's music video featured a woman giving birth. Though there was speculation on social media that the track may have actually been more about their unborn baby, the co-writer of the song, Annet Artani, shut those rumors down. The songwriter told TMZ that an abortion or unborn baby never came up during the writing process, and even noted that it was mainly about Artani's own recent breakup — Spears and Timberlake had actually been over for nine months by the time they wrote the lyrics.

2003: Spears shaded Timberlake for speaking on their intimacy

In 2003, Britney Spears got very candid about her sex life, which, as you can imagine, led to plenty more Justin Timberlake talk. It all went down when the star chatted with W (via CBS News), saying, "I've only slept with one person my whole life," before clarifying that she waited for two years before being intimate with Timberlake. But it wasn't just candidness the Princess of Pop was serving up, as that confession came with a side of shade. Referring to the *NSYNC singer, she continued, "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." Ouch.

The comment related to a 2002 interview Timberlake did with Walters for "20/20" in which the veteran journalist referenced Spears's philosophy on waiting until marriage for sex and asked Timberlake, "Did you and she live up to this during your relationship?" He burst into laughter and said, "Sure." That same year, Timberlake also showed some questionable behavior during a radio interview with "Star and Buc Wild" (via The New York Times), replying with a laugh, "Okay, yeah, I did it" when asked if he "f***ed" Spears during their relationship.

2003: Spears' infamous Diane Sawyer interview

How could we forget this one? Britney Spears had an infamous interview with Diane Sawyer in 2003 in which she was heavily questioned about the demise of her and Justin Timberlake's romance in a pretty shocking way. "You did something that caused him so much pain, so much suffering. What did you do?" Sawyer asked Spears of the highly publicized split.

Spears responded, "I was upset for a while. I think we're both really young, and it was kind of waiting to happen. And I will always love him." Spears then called Timberlake "such a great person" and broke down in tears during the interview, while Sawyer asked if she'd "betrayed" her ex. The interview resurfaced in 2021 when it was featured in the "Framing Britney Spears" documentary, causing some media outlets to condemn it.

As the interview gained attention all over again, Britney Spears had her say on Instagram in December 2021. "Something I never shared when I had that big break up years ago was that I couldn't talk afterwards ... I never spoke to anyone for a very long time ... I was in shock," she wrote in the now-deleted upload (via Yahoo! Entertainment), claiming her family "forced" her into the interview. Britney also stated that she didn't really understand what was happening because she was so young, but wrote of Sawyer, "she can kiss my white ass."

2013: Timberlake was accused of calling Spears 'some b***h'

For a long while, nothing much of note happened between Britney Spears and Justin Timberlake, but, obviously, the public's fascination most definitely hadn't come to an end. In 2011, Timberlake was asked about Spears by Vanity Fair and admitted he hadn't spoken to her in around a decade. "I wish her the best, that goes without saying. We were two birds of the same feather — small-town kids, doing the same thing. But then you become adults, and the way you were as kids doesn't make any sense. I won't speak on her, but at least for me, I was a totally different person. I just don't think we were normal; there was nothing normal about our existence."

While that was pretty drama-free, fast-forward two years and you'll find what many thought was a lot of shade. As we know, "Cry Me A River" was inspired by their break-up, and Timberlake had a lot to say before performing it at the DirecTV Super Bowl concert in 2013. "Sometimes in life, you think you found the one, but then one day you find out that she is just some b***h," he said (via E! News) before belting out the hit. Yikes.

Naturally, fans assumed that was a shady remark aimed at the Princess of Pop, though Timberlake denied this after the rumor mill went into overdrive. "Ok. I see you. Wouldn't disrespect ANYONE personally. Ever. #Relax #ItsBritneyBitch I do love that saying though *with accent* #Respect," he tweeted.

2020: Spears loves dancing to her ex's music

We've now grooved our way into the 2020s, when Britney Spears started showing off her penchant for dancing to her ex's music. Spears has shared several Instagram videos using her ex's tracks, including one where she moved to "Filthy" and directly referenced him in the caption. "PS I know we had one of the world's biggest breakups 20 years ago.... but hey the man is a genius!!!! Great song JT!!!!! Psssss if you KNOW WHAT'S GOOD!!!!!" she wrote alongside the April 2020 video (via People), which has been deleted. Timberlake clearly appreciated the shoutout, as he actually replied in the comments section with a crying laughing face and praising hands emoji.

That's not the only time Spears has danced to her former man's hits on social media, though. January 2021 brought a tag from Spears (yes, she actually tagged her ex this time) when she danced to Timberlake and Jay-Z's "Holy Grail." This one's also been deleted, but she wrote on the caption that time (via Metro), "Danced in my black [turtle] neck last week to HOLY GRAIL !!!! I KNOW ... turtle necks are SO ME !!!! @justintimberlake."

But Spears wasn't done there. Following speculation that Timberlake's "Blue Ocean Floor" could be about their split (though that's never been confirmed) Spears got her groove on to the song in yet another since-deleted Instagram video in November 2021 (via YouTube).

2021: Timberlake's apology to the women he has hurt, including Spears

Here's where things get serious once again between Britney Spears and Justin Timberlake. February 2021 saw the release of the bombshell documentary, "Framing Britney Spears," which shed some light on Spears's conservatorship battle as well as the way she's been treated, particularly by the media, during her career. The documentary also zeroed in on Timberlake's past comments about the star (including those questionable sex confessions we mentioned earlier). Plenty of fans called Timberlake out on social media as a result, while the media also began to question the singer's past behavior. 

"Justin Timberlake is just starting to trend, people are shocked to discover how much they didn't know..." one person tweeted, continuing in part, "[Like] how he told everyone about there [sic] private life. He had never apologize for this. He needs to be part of WE ARE SORRY BRITNEY." Another tweeted, "This tweet is for Justin Timberlake and Justin Timberlake only. So. If you're not Justin Timberlake, keep scrolling. Justin. Justin. Apologize to Britney Spears."

And apologize he did. After once again having his name hit the headlines alongside Spears's, Timberlake issued a public apology to the star and Janet Jackson — let's not forget that infamous Super Bowl controversy — in an Instagram post. The "Mirrors" singer wrote in part, "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."

2021: Timberlake and wife Jessica Biel sent love to Spears during conservatorship battle

Justin Timberlake wasn't quite done speaking publicly about Britney Spears yet. "Framing Britney Spears" brought the star a lot of support when it came to Spears's very controversial conservatorship, and saw plenty of high-profile celebrities publicly support her right to freedom. One of those famous faces? Timberlake himself. In June 2021, he posted a lengthy message to X, formerly known as Twitter, on behalf of himself and his wife, Jessica Biel, after Spears got very candid in a virtual court appearance about the abuse she'd suffered due to the conservatorship (via Variety).

"We should all be supporting Britney at this time," he wrote. "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."

Timberlake was one of several stars to speak out publicly in support of Spears as she fought for her conservatorship to cease, including Paris Hilton, Miley Cyrus, and Adele. It was ruled by a judge in November 2021 that Spears' conservatorship would come to an end.

2023: Timberlake reacts to Spears' memoir

After the release of Britney Spears's October 2023 memoir, "The Woman in Me," Justin Timberlake found himself in the spotlight ... and not for favorable reasons. With Spears's revelations, fans learned not only about the abortion Timberlake pushed for her to get during their time together (covered previously), but about his numerous infidelities. Within the pages of the book, Spears shares that she was very aware of his extracurricular activities, sharing (via Vanity Fair), "There were a couple of times during our relationship when I knew Justin had cheated on me. Especially because I was so infatuated and so in love, I let it go, even though the tabloids seemed determined to rub my face in it."

These revelations resulted in a whole lot of backlash for Timberlake, who, according to The U.S. Sun, had "big concern" about the information souring his upcoming music comeback. A source told the outlet that the former boy bander had been plotting his comeback for months prior to the book's release, and that he has been worried "the entire campaign will be centered on his reaction to the Britney stories and derailed by that narrative."

Though Timberlake has yet to make a public statement, a source told Entertainment Tonight in the wake of the bombshells, "Justin has been focusing on his own family and trying not to concern himself with Britney's memoir. In recent years, Justin has tried to be supportive of Britney from a distance. They dated so long ago, but he still has respect for her. Justin and Jessica just want everyone to grow and evolve instead of continuing to bring up the past."