A Complete Timeline Of Britney Spears And Justin Timberlake's Relationship

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 skimpy schoolgirl costume and bleach blond curly hair imprinted on America's hearts — and everything that's happened between them since.

A childhood meeting

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.

On "Rich And Famous," Spears later remembered of officially dating 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!'" 

As for what Timberlake had to say about those early years? "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 People), having previously told ABC News that he gave Spears her very first kiss. Cute!

A picture-perfect romance

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.

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!

2001 was the year that gave us some of those iconic ensembles, too. It was the year of those infamous matching denim outfits at the American Music Awards (which will be etched into our memories forever) and those adorable jerseys with the words "Pinky" and "Stinky" (their nicknames for one another) written across the back. Cementing their romance even more? Aerosmith invited *NSYNC and Spears to perform the Super Bowl XXXV halftime show, and Timberlake popped in when Spears hosted "Saturday Night Live."

Britney Spears and Justin Timberlake's split shocked the world

Despite everything seeming picture-perfect between Britney Spears and Justin Timberlake, the two split suddenly in March 2002 — shortly after Spears gushed on "The Oprah Winfrey Show" 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." Can you hear the sound of our breaking hearts here?

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 (now 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."

Cry J.T. a river

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 cheated, while the music video even features a Spears lookalike, which she alluded to on Instagram in 2021. "wait I look like that girl in the Justin Timberlake video with that hat in Cry Me A River !!! Oh s**t that's ME !!! I'm Britney Spears ??? I guess I forget that sometimes," she teased.

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 then revealed in his 2018 book, "Hindsight: And All the Things I Can't See in Front of Me," that he penned the track in just two hours. "The feelings I had were so strong that I had to write it, and I translated my feelings into a form where people could listen and, hopefully, relate to it," he said (via People).

As for Spears, rumors have swirled that she hit back via her 2003 hit "Everytime," though she doesn't appear to have publicly confirmed that.

That infamous Diane Sawyer interview

How could we forget this one? Britney Spears had an infamous "Primetime" 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. Viewers saw footage from the "Cry Me A River" music video. 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 (something her dad, Jamie Spears, has denied). 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."

Britney shades Justin

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, saying (via Entertainment Weekly), "I've only slept with one person my whole life," before clarifying that she waited for two years, until she was 19 years old, 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' 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," replying with a laugh, "Okay, yeah, I did it" when asked if he "f***ed" Spears (via The New York Times).

Though Timberlake himself hasn't appeared to publicly respond to Spears' comments, an alleged friend had his back, telling New York Daily News (via Entertainment Weekly), "He did not 'sell her out.' It's a wild accusation from someone who looks embarrassingly desperate." Yeah, it's safe to say things have turned nasty.

Can't stop the tweeting

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. "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 before belting out the hit (via E! News). 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.

Britney Spears loves dancing to Justin Timberlake'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." The former boybander didn't appear to publicly respond that time.

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).

Justin Timberlake's apology

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' 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 told you about 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', 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."

Justin Timberlake and Jessica Biel sent love to Britney Spears

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 her 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 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).

Timberlake wrote in part, "...we should all be supporting Britney at this time. 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 appeared to be specifically referencing Spears' claim that she was forced to be on birth control, despite wanting another child.

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.

Britney Spears thinks her ex used her for attention

Britney Spears wasn't quite ready to say "Bye Bye Bye" to talking about Justin Timberlake by the time 2022 rolled around, as the mom of two seemingly took aim at her ex in a very public way in March. Spears got candid in a lengthy Instagram post, addressing both her family and her former boyfriend. "I had a calling last night from Jesus and you know what he said ??? 'Dear child ... your mom had a serving with her book at the exact time when you needed her most ...all for WHAT ??? FAME and ATTENTION !!!! Your ex did the same thing ... he served with his first album using your name claiming you did him dirty !!!!," Spears wrote in the since-deleted post (via Newsweek).

Timberlake doesn't appear to have responded publicly, but that wasn't the last time his and Spears' names were grouped together for a headline. In April 2022, Gossip Bae paparazzi caught Timberlake out and about and couldn't help but quiz him on his thoughts about Spears announcing she was pregnant with her fiance Sam Asghari's baby. Timberlake clearly didn't want to be bothered, shooing the shutterbug and saying, "Stop! Go away." Spears tragically later confirmed on Instagram that she had suffered a miscarriage

Justin Timberlake and Britney Spears have both had a lot to say. Something tells us this won't be the last time the two are caught chattering about one another.