Head-Turning Things About Justin Timberlake And Britney Spears' Relationship

To many, it feels like a lifetime ago that Britney Spears and Justin Timberlake shared a passionate love that was all-consuming — for them and for their adoring fans. Over the course of their relationship, the world watched from the outside, gluing together the pieces of a young love that seemed to end far too soon. The two first met when they were just starting out in the industry and managed to build a friendship that lasted many years. That friendship was the basis for a headline-making romance that had fans yearning for more — even when it was over.

This period in pop culture history may someday be forgotten, but the public is getting to relive it in a very different way. In Spears's memoir, "The Woman in Me," released in October 2023, the pop star shared some of the most intimate details about her romance with Timberlake. With her written words, she has whisked us back to a world we thought we knew everything about, and we're getting some of the answers we never knew we needed. Throughout the course Spears and Timberlake's relationship, there have been so many head-turning moments, and we're taking a look at some of the biggest.

Britney Spears and Justin Timberlake first met when they were both cast on the Disney Channel reboot of "The Mickey Mouse Club." At the time, both Spears and Timberlake were just starting out on their individual roads to stardom — as just pre-teens. 

"Being in the show was boot camp for the entertainment industry: extensive dance rehearsals, singing lessons, acting classes, time in the recording studio, and school in between," Spears wrote in her memoir, "The Woman in Me" (via People). Although there were many other future big names on the cast — including Ryan Gosling — Spears admitted that one person in particular caught her eye. "I quickly connected with a boy named Justin Timberlake," she reminisced.

The year was 1992 and Spears and Timberlake were both quite young; just two kids getting an opportunity that would change their lives in more ways than they could imagine. Not only did the two end up launching respectable careers in the music industry years later, but they also shared a bond that eventually turned into something really special. That unique bond led Spears and Timberlake back to one another and they eventually took their friendship to the next level. 

It turns out that feelings between Justin Timberlake and Britney Spears were mutual when they first met, but they were just so young. They progressed forward like any other kids growing up in the '90s would; they hung out with other friends, had sleepovers, and played games, like Truth or Dare. In Spears's memoir, she actually revealed that her first kiss with Timberlake happened years before they became boyfriend and girlfriend. Sure enough, it took place during a game of Truth or Dare at a sleepover they both attended. "Someone dared Justin to kiss me. A Janet Jackson song was playing in the background as he leaned in and kissed me," Spears recalled in her memoir (via People). Ah, young love.

The revelation is interesting, however, as fans had long thought that Timberlake and Spears didn't actually develop any sort of romantic feelings for one another until they reunited at the beginning of their music careers. Spears has made it clear that there was something there with Timberlake — call it a schoolyard crush, if you will — very early on. Chances are, their "Mickey Mouse Club" friends knew they were into each other, hence the dare sent Timberlake's way. We don't know how to properly explain how puppy love in the '90s worked ... you just had to be there.

As the years went on, Britney Spears and Justin Timberlake embarked on very different journeys, despite both being in the music industry. Timberlake was linked with four other guys to create one of the most popular boy bands ever — NSYNC — while Spears pursued a solo career. NSYNC was headlining sold out shows all over the United States, and Spears was left trying to find her own fanbase while recording music and making small appearances. Then, in 1998, Spears got an opportunity to head out on her first-ever tour ... opening for NSYNC.

It didn't take long for rumors about Spears's love life to start circulating, and some fans thought that she was dating Timberlake while others were convinced that she had a thing with Lance Bass. Spears totally played coy about her personal life whenever she was asked, saying she was focused on her music career. "Overseas they say it's Nick Carter of Backstreet Boys," she joked to Rolling Stone in 1999. "I have no feelings at all." 

But everyone knows that was an outright fib, as the couple later revealed that they had made it official before her "...Baby One More Time" album was released in 1999. Spears and Timberlake kept their romance quiet for a bit, but made things public at the 2000 MTV Video Music Awards. From that point forward, the two were inseparable. Photos of them together covered magazines, and their relationship became the epitome of young love in Hollywood.

Britney Spears and Justin Timberlake's friendship was the baseline for their romance, and the two couldn't deny that they really loved each other. However, they were so young when they first met — and even when they started dating — so things progressed differently than other relationships. Not to mention, both Spears and Timberlake were super famous and really couldn't go anywhere without screaming fans trying to get close to them.

In a 2001 interview with The Guardian, Spears talked about the very first house that she owned since becoming famous. "I love showing off my house. I can't wait to start having dinner parties here," she told the outlet. But there was something even more surprising that came out of that interview aside from Spears wanting to throw dinner parties at age 19: Her boyfriend also lived with her.

Perhaps it was the need for privacy or simply the fact that Timberlake and Spears were so in love that they couldn't stand to be apart, but the two cohabited in Spears's home whenever they weren't on the road. "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 told the outlet.

Sadly, young love didn't stand the test of time — or temptation. For years, people speculated that Britney Spears stepped out on Justin Timberlake, hooking up with choreographer Wade Robson. In her 2023 memoir, Spears confirmed that very rumor.

"We were out one night and we went to a Spanish bar. We danced and danced. I made out with him that night," she wrote in the book, according to The U.S. Sun. This was the first time that Spears had ever confirmed cheating on Timberlake, though she also posited that it wasn't exactly the end of their relationship. Spears wrote that she told Timberlake what happened and the two stuck things out until they eventually broke up in 2002. But that's not all the tea that Spears spilled in her book.

In "The Woman in Me," Spears claimed that Timberlake also cheated on her while they were together. She didn't name the person who he cheated with, but she does know who and said it was "another celebrity," per TMZ. Spears chose to keep the details private because that person has moved on and has a family, and Spears clarified that she didn't want to cause any unnecessary issues. If nothing more, it's clear that the split wasn't just one-sided, like the media often portrayed it to be at the time.

After the split with Britney Spears in 2002, Justin Timberlake was hurting something fierce. He channeled that heartbreak into his music and released a song titled "Cry Me a River" later that year. The lyrics were about a tumultuous breakup and gave fans a peek into Timberlake's failed relationship with Spears. "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," a torn-up Timberlake sang. The track was an instant hit for Timberlake and ended up being one of his most popular singles of all time.

However, the song itself wasn't what really got people talking. As if Timberlake needed to make it clear who "Cry Me a River" was about, he went the extra mile to really drive it home. The music video for the song featured a Spears look-alike that had the Internet in an utter frenzy. At one point during the video, Timberlake follows a blond woman wearing a hat that is a ringer for Spears's headwear style of the time. After the track's release, Spears did what any other pop star ex-girlfriend would do in this situation; she responded with a song of her own.

In many ways, Britney Spears took the high road when she responded to Justin Timberlake's "Cry Me a River." It took a couple of years, but in May 2004, Spears released the single, "Everytime," one of the first songs that she had ever written herself. The ballad is about lost love that offers a message to a special someone, and fans have been led to believe that the track is a direct response to Timberlake's song. "I may have made it rain / Please forgive me / My weakness caused you pain / And this song's my sorry," Spears sings as an apparent apology to her ex.

In a 2004 interview with MTV, Spears explained her intention behind the song's meaning. "It's about heartbreak, it's about your first love, your first true love. That's something all people can relate to, because you all have that first love that you think you're going to be with the rest of your life," she said, perhaps further proving that she wrote the song with Timberlake in mind. While Spears didn't choose to have a Timberlake doppelgänger in her music video for the tune, there may have been some hidden messages in the video that wouldn't be uncovered until 2023.

Perhaps one of the biggest bombshells to come out of Britney Spears's 2023 memoir was that she was pregnant with Justin Timberlake's baby while they were together. "It was a surprise, but for me, it wasn't a tragedy ... 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," Spears wrote (via People). She went on to reveal that she and Timberlake made the decision to terminate the pregnancy. "To this day, it's one of the most agonizing things I have ever experienced in my life," Spears admitted.

After this revelation, fans have taken another look at the music video for "Everytime," which features a hospital scene after Spears's character dies by suicide. In the scene, a woman lies in a hospital bed with her newborn baby, and fans believe that the imagery may be a nod to Spears's unborn baby. "Everytime by britney spears has a whole different meaning now," one person wrote on X, formerly known as Twitter.

Britney Spears's heartbreak following her split from Justin Timberlake stayed with her for years. Although things didn't end the way the two had hoped, they both admitted that their love for one another would last a lifetime, even if they didn't end up together. In Spears's interview with Diane Sawyer (via Us Magazine) in 2003, she passionately spoke about her past relationship with Timberlake. "I was upset for a while. We both are really young and it was kind of waiting to happen. I will always love him ... he is such a great person," she opened up.

Spears isn't the only person in the former twosome that felt this way, either. "I feel like I'm in the middle of a soap opera. I honestly know what it's like to have a broken heart," Timberlake told People in 2002 after the split. "I love Britney, and I'll always love her."

While neither could deny the strong love they once shared, Spears and Timberlake grew apart over the years and went on to have families with other people. Spears married Kevin Federline and welcomed sons Sean Preston and Jayden James in 2005 and 2006 respectively. Meanwhile, Timberlake married actor Jessica Biel in 2012 and they have two children together; Silas and Phineas.

It's no secret that both Britney Spears and Justin Timberlake had a rough time in the aftermath of their split. In a 2006 interview with GQ (via CBS News), Timberlake expressed that he was upset with his ex for not having his back. "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, referring to "Cry Me a River."

Even though years had gone by since that time of heartbreak and sadness, Timberlake maintained that his love for Spears was like lightning in a bottle. "I was in love with her from the start. I was infatuated with her from the moment I saw her," he explained to the publication. Certainly, Spears and Timberlake didn't stick up for one another much at all in the freshness of everything that transpired with their breakup, but what does anyone expect from two young lovers scorned?

There was something very different about Britney Spears and Justin Timberlake's relationship that no one could deny. Whether it's the way they met or how they ended up falling so deeply in love when they were so young, the way they looked at one another was just magic. But in 2011, Timberlake tried to explain it. "I just don't think we were normal; there was nothing normal about our existence," he told Vanity Fair. "We spent way too much time being the biggest thing for teenyboppers."

Aside from not being "normal," Timberlake also revealed that he still wanted nothing but the absolute best for his ex — who was basically on her world domination comeback tour. Years after shaving her head and going after a member of the paparazzi with an umbrella, Spears had released "Femme Fatale" and was at the top of her game once again. Interestingly, however, through everything she had been through, Timberlake revealed that he didn't reach out to her once. "We haven't spoken in 9 or 10 years," he told Vanity Fair. Sure, we understand that it's not customary for exes to keep in touch, especially when things ended poorly. But not even a text to check in when Spears went through a traumatic time in her life? Regardless, the former couple has maintained a mutual respect for each other over the years.

Britney Spears's romantic feelings for Justin Timberlake may be completely out of sight these days, but that doesn't mean that she has any ill will toward him. In fact, during one of her Instagram tirades, she actually gave him a shout out — and he responded.

"This is my version of Snapchat or TikTok or whatever the cool thing you're supposed to do these days," Spears captioned an Instagram post in 2020 (via People). In the accompanying video, she was dancing along to Timberlake's 2018 song, "Filthy." Then, she unexpectedly addressed their split. "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!!!!!" she added. 

In response, Timberlake popped up in the comments section of the post, offering a crying with laughter emoji and three high-ten emoji. This marked one of the very first public interactions Timberlake and Spears had since their split.

It seems that with time to mature and grow, Justin Timberlake reassessed his actions towards Britney Spears back when they were dating and in the aftermath of their split. In 2021, Timberlake issued a public apology to Spears by way of a candid upload to Instagram. In the post, Timberlake expressed his regret over his actions with Spears as well as Janet Jackson, who was practically exiled from the music industry after the wardrobe mishap at their 2004 Super Bowl performance. He explained that he came to understand the privileges he has received in the industry simply for being a white man.

"Because of my ignorance, I didn't recognize it for all that it was while it was happening in my own life but I do not want to ever benefit from others being pulled down again," Timberlake wrote. "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 will do better."

Timberlake's words came in the middle of Spears's battle against her long-standing conservatorship. The "Toxic" singer didn't respond to her ex's apology at the time.   

Britney Spears spent over 13 years of her life living within the limitations of a conservatorship that was controlled by her father, Jamie Spears. In 2021, Britney went to court in an effort to convince a judge that she not only was capable of managing her own life, but to begin the process of speaking out for herself after she revealed she was abused within the conservatorship, forced to work, and even held against her will. After one of Spears's court appearances in June 2021, her ex-boyfriend released a statement to show his support.

"After what we saw today, we should all be supporting Britney at this time," Timberlake 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." He continued in a thread, "No one should EVER be held against their will ... or ever have to ask permission to access everything they've worked so hard for. 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," he added.

Spears's conservatorship was eventually terminated months later in November 2021. After all that these two have been through, it seems that they have each moved on and let bygones be bygones. Besides the grievances Spears has aired out in her 2023 memoir, of course.