What was Britney Spears and Justin Timberlake’s relationship like? How did the relationship work against Spears’s favor?
Spears and Timberlake dated from 1999 to 2002. In her memoir The Woman in Me, Spears reveals shocking details about their relationship, including a hidden abortion and how the media turned against her after their split.
Continue reading to learn more about the tumultuous relationship.
Living in the Limelight (1999-2003)
The tremendous success at the start of her career swept the pop star into a world she could have never imagined and kicked off a period of creativity and excitement, which included Britney Spears and Justin Timberlake’s relationship. Thrust into the spotlight, she rubbed shoulders with celebrities of whom she’d always been in awe. Between recording albums and going on tour, a host of new opportunities arose, such as commercials, acting roles, and even a spot in the 2001 Super Bowl halftime show. With the income from her music, she was able to provide for her family, building the house that her mother always wanted and digging her father out of his business debts. Spears says that she was also maturing as an artist, and her 2001 Dream Within a Dream tour was staged and choreographed to highlight that fact with top-of-the-line production and design.
(Shortform note: The Super Bowl championship game for the US’s National Football League is seen by over 100 million viewers. For musicians like Spears, the show at the game’s midpoint brings the largest single audience they’ll ever have in their careers. The Super Bowl halftime program has become more elaborate over the years, as have the tour productions of major music artists. Performers such as the Rolling Stones and Madonna spend millions of dollars on stage design and setup. Should Spears tour again, a similar production scale would pay off—experts guess that a future tour by Spears would make at least $300 million in sales.)
Romance and Heartbreak
This period of her life also brought difficulties, however. In 1999, Spears toured with her childhood co-star Timberlake, who’d become a member of the pop group NSYNC, and became romantically involved with him. The couple lived together in Orlando, Florida, and though their relationship wasn’t spotless, Spears felt so strongly for Timberlake that she overlooked his various affairs. Spears states that she only cheated on him once and that she told him about it so they could move on. When Spears became pregnant with their child, Timberlake pushed her to have an abortion, insisting that they were too young to be parents. To keep her pregnancy and abortion secret, Spears didn’t go to a doctor, but took pills to force a painful miscarriage.
(Shortorm note: Unlike contraceptive morning-after pills, the abortion pills available for Spears to use were a combination of mifepristone and misoprostol that was approved by the US Federal Drug Administration (FDA) in 2000. The cramping and heavy bleeding that Spears describes are expected as part of the medication abortion process, as well as vomiting, diarrhea, and fatigue. Critics of abortion pills argue that doctors and family planning clinics underplay their risks, but the FDA insists that multiple clinical trials and studies have demonstrated the drugs’ safety.)
Spears writes that left to herself, she wouldn’t have ended her pregnancy, but she did so for Timberlake’s sake. Nevertheless, he ended their relationship in 2002, breaking up with her via text message while she was filming a music video. Timberlake would go on to write a solo album painting Spears as a horrible girlfriend who broke his heart.
(Shortform note: Timberlake released his debut album in 2002, a year after the breakup of NSYNC. Though he’d never specify that any of its songs were about Spears, he says he wrote the specific one she mentions—“Cry Me a River”—because he felt angry and mistreated. Though Spears devotes several chapters to their romance, Timberlake’s 2018 memoir Hindsight only mentions her once and omits other controversies in his career, such as the infamous wardrobe malfunction during his Super Bowl duet with Janet Jackson. Timberlake is now married to actress Jessica Biel, with whom he has two children.)
During her breakup with Timberlake, Spears had no one to turn to—she didn’t feel allowed to drop her confident pop star image and had no forum to tell her side of the story. As she had during dark times as a child, Spears chose to hide—first by going home to Louisiana, and later by retreating to an apartment in New York.
(Shortform note: Spears’s withdrawal from the spotlight is a common, though ineffective, response to shame. In So You’ve Been Publicly Shamed, Jon Ronson lists several examples of times in which hiding from the public eye backfired on people and made their situations worse. When someone is shamed, withdrawing from the world only increases their isolation, and the shaming may continue anew as soon as they step out from their safe place.)
