He might be crying a river.
Somewhere in the Hollywood Hills, the PR team for a boy band legend is working on overdrive to deal with the biggest crisis that could possibly come their way: One of the most famous women on the planet has released a tell-all, and more than one chapter of that tell-all is dedicated to the man they’ve been hired to protect.
Just kidding. No one knows what Justin Timberlake or his team thinks about Britney Spears’ new memoir, The Woman in Me. Here is what we do know for certain, though, after years of teeth-gritting, finger-tapping anticipation for the release of this book: Spears has a whole lot to say about her time dating Timberlake, and not much of it is very pretty.
How long did Justin Timberlake and Britney Spears date?
Before we get into the nitty gritty (and we assure you, it is extremely nitty and very gritty), here’s a quick crash course on their relationship timeline to refresh you: According to Spears’ memoir, she first kissed Timberlake while they were kids performing on The Mickey Mouse Club. Several years later, the two began to date in earnest as teenagers and rising pop stars. Spears describes their relationship as being founded on a sort of undeniable magnetism. “You couldn’t explain the way we were together,” Spears writes. “It was weird, to be honest, how in love with each other we were.”
Timberlake and Spears dated from 1999 to 2001. Their relationship coincided with the exact moment the two rocketed to fame, both as a couple and as individual musicians in their own right. When they broke up, speculation about the cause of the breakup ran rampant. (Don’t worry, we’ll get to all that below.)
In the years since both individuals went on to marry and have children. In Timberlake’s case, he married actress Jessica Biel. The two are still together and have two children. In Spears’ case, she married and had two children with dancer Kevin Federline. The pair were divorced in short order. Spears has since married and been divorced two more times.
Now her memoir is dominating the airwaves, and for good reason: The tea has been spilled — but not just about her love life; she reveals a lot about her upbringing, family, and, of course, career. But Timberlake is at the top of everyone’s minds right now. So, below, you’ll find the most explosive stories Spears shared about her ex in her memoir. It’s worth noting (as we briefly mentioned above) that neither Timberlake nor his reps have publicly responded to the allegations made in her memoir yet — so from here on out, you’re hearing the story as told through The Woman in Me.
Justin Timberlake encouraged Britney Spears to get an abortion
One of the most startling revelations from Spears’ memoir is that Timberlake allegedly pressured her into getting an abortion while they were together.
“[The pregnancy] was a surprise, but for me, it wasn’t a tragedy,” she writes in the book. “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. 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.”
Spears said she didn’t personally want to have an abortion at the time. “If it had been left up to me alone,” she explains, “I never would have done it. And yet Justin was so sure that he didn’t want to be a father…To this day, it’s one of the most agonizing things I have ever experienced in my life.”
According to the pop star, “It was important that no one find out about the pregnancy or the abortion, which meant doing everything at home. Spears says she used the abortion pill, then “went into the bathroom and stayed there for hours, lying on the floor, sobbing and screaming.”
Then, Timberlake apparently decided to soothe Spears with a tactic only a teenage pop sensation would find appropriate for the given moment: He performed for her.
“At some point, he thought maybe music would help, so he got his guitar and he lay there with me, strumming it,” Spears notes. “[The experience] messed [me] 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.”
Timberlake “slept around” while he was dating Spears
Up until now, the mainstream, culturally-agreed-upon explanation for Timberlake and Spears’ breakup was that Spears cheated on Timberlake. This theory was endorsed via Timberlake’s less-than-subtle album, Justified, which came out the year after the breakup and included the now-infamous song, Cry Me a River.
Now, Spears appears to be setting the record straight: It was Timberlake who cheated throughout their relationship, she says.
“There were a couple of times during our relationship when I knew Justin had cheated on me,” Spears writes. “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. 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.”
Spears listed another alleged affair of Timberlake’s, which came to light after he outed himself to one of her dancers. “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,'” Spears recalls. “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.”
According to Spears, these incidents happened frequently enough for her to develop a certain level of disassociation with the infidelity. “Clearly, he’d slept around,” she says. “It was one of those things where you know but you just don’t say anything.”
Spears also admitted that she cheated on Timberlake at the very end of their relationship, with a choreographer named Wade Robson. “[Wade and I] were out one night and we went to a Spanish bar,” she says. “We danced and danced. I made out with him that night.”
From Spear’s perspective, it wasn’t necessarily the cheating that caused their relationship to end — it was also the work Timberlake was doing on his first solo album, Justified. “When Justin began making [Justified], he started being very standoffish with me,” Spears writes. “I think that was because he 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.”
Timberlake broke up with Spears with a two-word text
After all those years of puppy love, then that painful phase of cheating, and a heartbreaking abortion, how did Spears and Timberlake finally part ways?
With a two-word text message. And a lot of exclamation points.
To be specific, Timberlake texted Spears, “It’s over!!!”
This is, on its own, an extremely dramatic way to end a relationship — but when you take into consideration the fact that it was 2001 and people were barely texting at that point, the move takes on a new level of surreality.
While the other allegations made by Spears about Timberlake have yet to be reinforced or disputed publicly by other eyewitnesses, this one actually has been. Spears was on set filming a music video for her song Overprotected when she received the text message. The director for the music video, Chris Applebaum, confirmed to Page Six earlier this year that he saw the text message with his own eyes.
Per Applebaum, Spears disappeared from set at some point late in the day, which is a big deal when it costs “20 grand to sit around.” He found her in her trailer, crying, which is when she showed him the text message from Timberlake. Applebaum said Spears was utterly distraught when she received the message, and that the whole day of filming nearly fell apart as a result.
Applebaum said to Spears, “If you don’t have it in you, I totally understand. But if you want to go out there and finish this last set-up in the rain, you can show [Timberlake] that he just made the biggest f—ing mistake of his life.”
Spears went out and finished the work day. (One thing about Spears that even the greatest critic cannot deny: the woman has a serious work ethic.)
“As much as Justin hurt me, there was a huge foundation of love, and when he left me, I was devastated,” Spears writes. “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.”
Timberlake also wrote — and then framed — a breakup letter for Spears
After the breakup, Spears said, she stopped speaking and went home to Kentwood, Louisiana. “I lay in my bed and stared at the ceiling,” she says of that time period.
Then Timberlake flew out to Louisiana to see Spears.
“He brought me a long letter he’d written and framed,” she recalls. “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.”
When Spears read the letter, her first thought was: “Damn. He’s a good writer. Because that was exactly how I felt…It almost felt like I was suffocating. 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.”
When you’re dealing with a heartbreak so significant it feels like suffocation, you’d be forgiven for wanting some time to decompress. But Spears didn’t have that luxury. She was in the middle of touring, and so she moved through the devastation the only way she was able to: by continuing to work, day in and day out, like a professional.
When it comes to Spears’ memoir, these Timberlake confessions are merely the tip of the confessional iceberg. Spears’ memoir is available for purchase if you’re desperate to learn more.
