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Spears published her bombshell memoir, "The Woman in Me," on Oct. 24, and told all about her three-year relationship with the singer, which began in 1999, when she was 17 and he was 18.
Timberlake did not respond to multiple requests for comment from TODAY.com and NBC News on the contents of Spears' memoir.
He did issue an apology after a 2021 memoir about Spears came out called “Framing Britney Spears,” writing in an Instagram post, “The industry is flawed. It sets men, especially white men up for success. As a man in a privileged position I have to be vocal about this. 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.”
Here's everything she said about her relationship with the ‘N Sync frontman, from meeting on Disney's "The Mickey Mouse Club" to how she had "one of the worst days" of her life at the 2007 VMAS, "in the same exact place and time" that she said Timberlake had "one of his best."
Meeting Justin Timberlake
Spears writes she landed a role on "The Mickey Mouse Club" after she auditioned for the show for the second time. She then flew to Orlando, Florida, to film the show at Disney World.
“The Mouseketeers quickly split into our own cliques, divided by the dressing rooms that we shared: Christina Aguilera and I were the younger kids, and we shared a dressing room with another girl, Nikki DeLoach," she writes. "We looked up to the older kids — Keri Russell, Ryan Gosling, and Tony Lucca, who I thought was so handsome. And quickly I connected with a boy named Justin Timberlake.”
She writes that she later kissed Timberlake for the first time at a sleepover.
“Another time, at a sleepover, we played a game of Truth or Dare, and someone dared Justin to kiss me," she writes. "A Janet Jackson song was playing in the background as he leaned in and kissed me.”
Meeting again — and this time, they were 'N Sync
Spears writes she kept in touch with Timberlake once the show ended, and in 1998, she booked an opening act slot on 'N Sync's tour, where she writes that the pair enjoyed spending time together on the tour.
“Having shared that experience at such a young age gave us a shorthand. We had so much in common. We met up when I was on tour and started hanging out during the day before shows and then after shows too," she writes. "Pretty soon I realized that I was head over heels in love with him — so in love with him it was pathetic. When he and I were anywhere in the same vicinity — his mom even said this — we were like magnets.”
"His band, 'N Sync, was what people back then called 'so pimp.' They were white boys, but they loved hip-hop. To me that's what separated them from the Backstreet Boys, who seemed to very consciously position themselves as a white group. 'N Sync hung out with Black artists," she writes.
"Sometimes I thought they tried too hard to fit in," she continues, before recalling a story where Timberlake had taken her to parts of New York she had never been to before, where they ran into rapper Ginuwine.
"J got all excited and said, so loud, 'Oh yeah, fo shiz, fo shiz! Ginuwiiiiiine! What's up, homie?'" Spears recalls Timberlake shouting.
How she feels the press treated her differently from Timberlake
As Spears' fame grew, she writes she couldn't help but notice how the press treated her differently from Timberlake.
"I had a hard time being as carefree as he seemed. I couldn’t help but notice that the questions he got asked by talk show hosts were different from the ones they asked me," she writes. "Everyone kept making strange comments about my breasts, wanting to know whether or not I’d had plastic surgery."
But nonetheless, she describes that period of time in her personal life as "very happy."
"Justin and I lived together in Orlando. We shared a gorgeous, airy two-story house with a tile roof and a swimming pool out back. Even though we were both working a lot, we’d make time to be home together as often as we could … that was a good time in my life," she writes. "I was so in love with Justin, just smitten. I don’t know if when you’re younger love’s a different thing, but what Justin and I had was special. He wouldn’t even have to say anything or do anything for me to feel close to him."
Justin cheated — and she did too
But it wasn't all sunshine in their relationship, Spears writes. The singer says she knew Timberlake had cheated on her "a couple of times."
She specifically references photos catching him with a member of British girl group All Saints in a car in London, and separately, one of her dancers told her in Las Vegas he had “gestured toward a girl and says, ‘Yeah, man, I hit that last night.’”
“I don’t want to say who he was talking about because she’s actually very popular and she’s married with kids now. I don’t want her to feel bad. My friend was shocked and believed Justin was only saying it because he was high and felt like bragging,” she writes.
“There were rumors about him with various dancers and groupies. I let it all go, but clearly, he’d slept around. It was one of those things where you know but you just don’t say anything,” she continues.
Spears admits she also cheated on Timberlake once with dancer Wade Robson.
“We were out one night and we went to a Spanish bar. We danced and danced. I made out with him that night. I was loyal to Justin for years, only had eyes for him with that one exception, which I admitted to him,” she writes. “That night was chalked up to something that will happen when you’re as young as we were, and Justin and I moved past it and stayed together. I thought we were going to be together forever. I hoped we would be.”
Robson did not immediately respond to a request for comment from TODAY.com.
She was pregnant with Timberlake's child and had an abortion
Spears writes that at one point during their three-year relationship, she became pregnant with Timberlake's child.
"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. Besides, what was done was done," she writes.
"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. I could understand. I mean, I kind of understood. If he didn’t want to become a father, I didn’t feel like I had much of a choice. I wouldn’t want to push him into something he didn’t want. Our relationship was too important to me," she continues.
She says the pair decided to have an abortion: "I’m sure people will hate me for this, but I agreed not to have the baby."
Spears adds she had never imagined choosing abortion for herself until that moment.
“Abortion was something I never could have imagined choosing for myself, but given the circumstances, that is what we did. I don’t know if that was the right decision. 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 writes.
The pair decided she should not go to a doctor or to a hospital to have an abortion — a decision that she writes, "in retrospect wound up being, in my view, wrong."
"It was important that no one find out about the pregnancy or the abortion, which meant doing everything at home. We didn’t even tell my family," she writes.
She describes taking the pills, and then experiencing "excruciating cramps." She says she went into the bathroom and laid on the floor for hours.
"Justin came into the bathroom and lay on the floor with me. At some point he thought maybe music would help, so he got his guitar and he lay there with me, strumming it. I kept crying and sobbing until it was all over," she writes.
"It took hours, and I don’t remember how it ended, but I do, twenty years later, remember the pain of it, and the fear. After that, I was messed up for a while, especially because I still did love Justin so much. It was insane how much I loved him, and for me it was unfortunate," she adds.
Spears writes she "should have seen the breakup coming," but she didn't.
"When Justin began making his first solo album, "Justified,' he started being very standoffish with me. I think that was because he’d decided to use me as ammunition for his record, and so it made it awkward for him to be around me staring at him with all that affection and devotion," she writes.
"Ultimately, he ended our relationship by text message while I was on the set for the video for the 'Overprotected' remix by Darkchild," she adds.
She reflects on the breakup, more than two decades later, in the book.
"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 do was cry. I don’t know if I was clinically in shock, but it felt that way. Everyone who knew me thought something was wrong with me, really wrong," she writes.
She says she went back home to Louisiana, where she couldn't even talk to her family or friends.
"Justin flew out to Louisiana to visit me. He brought me a long letter he’d written and framed. I still have it under my bed. And at the end it said — it makes me want to cry to think about it — 'I can’t breathe without you.' Those are the last words in it," she writes.
She shares she thinks getting close to Timberlake's family contributed to making the breakup so excruciating.
“Part of what made that period of time so difficult is that Justin’s family had been the only real, loving family I had… my mom would come out and visit us every once in a while but she’s not who I went home to, ever," she writes.
On 'Cry Me a River'
After the breakup, Spears recalls seeing the video for Timberlake's single "Cry Me a River," which she describes as featuring "a woman who looks like me" who "cheats on him and he wanders around sad in the rain."
"In the news media, I was described as a harlot who’d broken the heart of America’s golden boy. The truth: I was comatose in Louisiana, and he was happily running around Hollywood," she writes.
She then went on to blast Timberlake for not mentioning that he had cheated on her, too.
"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? There’s always been more leeway in Hollywood for men than for women. And I see how men are encouraged to talk trash about women in order to become famous and powerful. But I was shattered. The thought of my betraying him gave the album more angst, gave it a purpose: s----talking an unfaithful woman," she writes.
She concludes: "'Cry Me a River' did very well. Everyone felt very sorry for him. And it shamed me."
She adds that she felt there was "no way" for her to tell her side of the story at the time.
"I couldn’t explain, because I knew no one would take my side once Justin had convinced the world of his version," she writes. "I don’t think Justin realized the power he had in shaming me. I don’t think he understands to this day."
At the 2007 VMAs and beyond
Spears mentions running into Timberlake backstage at the 2007 MTV Video Music Awards ceremony, where she performed "Gimme More."
"It had been awhile since I'd seen him. Everything was going great in his world. He was at the top of his game in every way, and he had a lot of swagger," she writes. "I was having a panic attack. I hadn't rehearsed enough. I hated the way I looked. I knew it was going to be bad."
She adds that she won't defend the performance "or say it was good."
"I will say that as performers we all have bad nights. They don't usually have consequences so extreme," she writes. "You also don't usually have one of the worst days of your life in the same exact place and time that your ex has one of his best."
"Justin glided down the runway into his performance. He was flirting with girls in the audience, including one who turned around and arched her back, shaking her breasts as he sang to her," she continues. "Then he was sharing the stage with Nelly Furtado and Timbaland — so fun, so free, so light."
She referenced Timberlake one more time in her memoir, when she was reflecting on her divorce from her second husband Kevin Federline.
"I was young, and I made a lot of mistakes. But I will say this: I wasn’t manipulative. I was just stupid," she writes. "That’s one thing Justin and Kevin ruined about me. I used to trust people. But after the breakup with Justin and then my divorce, I never really did trust people again."
TODAY.com has reached out to Federline for comment and has not heard back at the time of publication.
This article was originally published on TODAY.com