Long before Joe Jonas infamously broke up with Taylor Swift on a 27-second phone call, Justin Timberlake ended his three-year relationship with Britney Spears via a two-word text.
That’s just one of the many wild stories about the former *NSYNC member in Spears’s tell-all memoir, The Woman in Me, which officially dropped today. Spears and Timberlake dated from about 1999 until 2002 and reigned as the It couple of the era. Now, fans have a chance to relive their highly publicized relationship from Spears’s perspective, with the “Toxic” singer reflecting on the fallout of their romance in her new book.
Timberlake’s reps have so far not responded to various outlets’ requests regarding any of the claims Spears makes in the book, but history indicates that the exes may no longer have bad blood. Timberlake, who has been married to actor Jessica Biel since 2012, previously spoke out in support of Spears during her legal battle to end her 13-year conservatorship.
“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,” he tweeted in June 2021. “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.”
Ahead, we break down every eyebrow-raising tale about Timberlake that the pop star recounts in her book—including cheating allegations, their bittersweet breakup, and Spears’s previously unpublicized abortion.
1 | Britney knew Justin “slept around” while they were in a relationship together.
According to the singer’s claims in the book, Timberlake serially cheated on her throughout the duration of their three-year relationship.
“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,” she recalls, per an excerpt quoted by People. “When NSYNC went to London in 2000, photographers caught him with one of the girls from All Saints in a car. But I never said anything. At the time we’d only been together for a year.”
Timberlake allegedly bragged about his affairs, with one involving a now-famous individual. “Another time, we were in Vegas, and one of my dancers who’d been hanging out with him told me he’d gestured toward a girl and said, ‘Yeah, man, I hit that last night,’” she continues. “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.”
Spears says she knew about the “rumors about him with various dancers and groupies,” and although she “let it all go ... clearly, he’d slept around. It was one of those things where you know but you just don’t say anything.”
She also admits she cheated on Timberlake once with choreographer Wade Robson, after hearing about Timberlake’s escapades.
“[Wade and I] were out one night and we went to a Spanish bar. We danced and danced. I made out with him that night,” she writes, per an excerpt from The Sun. She and Timberlake ultimately “agreed to move past” the incident.
2 | Justin used African-American Vernacular English problematically.
Timberlake (who has a history of being accused of cultural appropriation) apparently had no qualms about hijacking AAVE as a white man.
As Spears writes, “His band NSYNC 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 very consciously to position themselves as a white group. NSYNC hung out with Black artists. Sometimes I thought they tried too hard to fit in.”
She recalls a specific incident during a visit to New York City, in which they encountered “a guy with a huge, blinged-out medallion who was flanked by two giant security guards.”
“J got all excited and said, so loud, ‘Oh yeah, fo shiz, fo shiz! Ginuwiiiiiine! What’s up, homie?’” she writes. Felicia Culotta, Spears’s assistant at the time, apparently mocked Timberlake’s butchered AAVE by doing an impression of him—though that hardly fazed the *NSYNC member. “J wasn’t even embarrassed,” says Spears. “He just took it and looked at her like, Okay, fuck you, Fe.”
3 | Justin played the guitar while Britney underwent an abortion.
The memoir reveals a previously unknown breaking point for Spears: that she became pregnant, and that Timberlake encouraged her to get 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 writes, in an excerpt published by 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.”
She adds, “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.”
Getting the abortion was ultimately heartbreaking for Spears. As she recalls, “To this day, it’s one of the most agonizing things I have ever experienced in my life.”
To avoid the public finding out about the pregnancy, they “decided on something that in retrospect wound up being, in my view, wrong, and that was that I should not go to a doctor or hospital to have the abortion,” according to an excerpt quoted by Vulture.
“It was important that no one find out about the pregnancy or the abortion, which meant doing everything at home,” the singer writes. Only Spears, Timberlake, and Culotta were aware of the abortion, executed through Spears’s ingestion of “the little pills.”
“I went into the bathroom and stayed there for hours, lying on the floor, sobbing and screaming. ... I went down to the ground on my knees, holding the toilet,” Spears recounts. In an attempt to soothe her, Timberlake lay on the bathroom floor with her. “At some point he thought maybe music would help, so he got his guitar and he lay there with me, strumming it. … Still, they didn’t take me to the hospital.” Spears says the event “messed [her] 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.”
4 | He broke up with her while she was filming a music video.
Timberlake allegedly ended their relationship via text while Spears was on the set of her video for “Overprotected (Darkchild Remix)”—an even more brutal blow considering that texting was a far less common mode of communication in 2002. (Director Chris Applebaum told Page Six the two-word text simply read: “It’s over!!!”)
“After seeing the message as I sat in my trailer in between takes, I had to go back out and dance,” Spears writes, per E! News. “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.”
The breakup caused Spears to temporarily consider leaving Hollywood for good. She even moved back to Kentwood, Louisiana, to recover from the aftershock.
“I barely left the house,” she describes. “I was that messed up. I lay in my bed and stared at the ceiling.”
5 | Justin gifted Britney a framed breakup letter—that she still keeps under her bed.
While Spears was in Kentwood, Timberlake visited her with an inconceivable gift: a framed breakup letter.
“He brought me a long letter he’d written and framed,” she recalls, per E!. “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.”
Still, the letter didn’t give her the closure she desperately wanted.
“It almost felt like I was suffocating,” Spears says. “Like I couldn’t breathe after all that happened. The thing is, though, even after I saw him and read the letter, I didn’t come out of the trance. He did all that, he came there to see me and I still couldn't talk—to him or to anybody.”
6 | Britney didn’t appreciate the narrative he weaved about her after their split.
She recalls the troubling period after their breakup, when Timberlake seemed to revel in both the spotlight and the public’s sympathy while Spears was branded a “cheating slut and a liar,” according to an excerpt published by Express. His music video for “Cry Me a River”—in which a Spears look-alike cheats on a depressed Timberlake—didn’t help matters.
“Was I mad at being ‘outed’ by him as sexually active? No. To be honest with you, I liked that Justin said that. Why did my managers work so hard to claim I was some kind of young-girl virgin even into my twenties? Whose business was it if I’d had sex or not?” Spears writes. Instead, what upset the pop star was how the narrative had been spun so that she looked like “a harlot who’d broken the heart of America’s golden boy.”
In an excerpt published in Entertainment Tonight, Spears writes, “The truth: I was comatose in Louisiana, and he was happily running around Hollywood. … The thought of my betraying him gave [his] album more angst, gave it a purpose: shit-talking an unfaithful woman … Everyone felt very sorry for him. And it shamed me.”
As an associate editor at HarpersBAZAAR.com, Chelsey keeps a finger on the pulse on all things celeb news. She also writes on social movements, connecting with activists leading the fight on workers' rights, climate justice, and more. Offline, she’s probably spending too much time on TikTok, rewatching Emma (the 2020 version, of course), or buying yet another corset.
