Looking back at Britney Spears and Justin Timberlake's relationship timeline

Britney Spears’ memoir, "The Woman in Me," hit shelves in October 2023, and its details put her relationship with ex Justin Timberlake under the microscope.

For much of the early 2000s, Spears and Timberlake held the mainstream’s attention in the palm of their hand.

Spears was 17 when she started dating Timberlake, who was 18. According to the singer’s memoir, by the time they called off their relationship in 2002, they had experienced a deep love and a terminated pregnancy.

TODAY.com reached out to representatives for Timberlake, Spears and the book’s publisher for comment but did not hear back.

In her memoir, Spears described her decision to have an abortion at the time as “one of the most agonizing things” she had ever experienced. Yet, back when they were in the throes of love and limelight, things weren’t always tragic. From their meet-cute as kids part of the Mickey Mouse Club to their coordinating outfits, there was a time in their lives when the couple appeared to be very much on the same page.

Spears and Timberlake seemed to have moved on in the years since their relationship. Today, Timberlake is married to actor Jessica Biel and they share two children. Spears, who shares two children with ex Kevin Federline, was married to Sam Asghari before they separated in 2023. Both stars have also continued to grow their careers in entertainment. Still, it’s hard not to look back at their early years.

Read on for a look back at their relationship.

1992 — Spears and Timberlake meet as kids on 'Mickey Mouse Club'

Before she was dubbed the pop princess of the 90s and early aughts, Britney Spears was a Mouseketeer. In 1992, Spears won a spot as a cast member of Disney’s reboot of “The Mickey Mouse Club” called “The All-New Mickey Mouse Club” and appeared alongside future fellow stars Christina Aguilera, Ryan Gosling, and Keri Russell and future flame Justin Timberlake.

In the excerpt from her memoir obtained by People, Spears reflected on her time in the series and kissing Justin for the first time while starring in the series.

“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. “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. We looked up to the older kids – Keri Russell, Ryan Gosling, and Tony Lucca, who I thought was so handsome. And I quickly connected with a boy named Justin Timberlake.”

“(Once) at a sleepover, we played Truth or Dare, and someone dared Justin to kiss me,” she continued. “A Janet Jackson song was playing in the background as he leaned in and kissed me.”

1999 — Spears and Timberlake step into the spotlight, hand-in-hand

Spears and Timberlake started dating in 1999.

That same year, Spears began performing around the country on her ...Baby One More Time Tour. The next year, in 2000, she went on her (You Drive Me) Crazy Tour.

Meanwhile, in 2000, Timberlake and 'N Sync released their hit album, "No Strings Attached."

Jan. 8, 2001 — Spears and Timberlake don all denim in a now-iconic style moment

The couple pushed the fashion benchmark in 2001 when they attended the American Music Awards in matching denim outfits. While Spears donned a strapless floor-length denim gown, Timberlake stepped out in an all-denim suite, including a denim cowboy hat.

In 2020, Timberlake appeared on 'N Sync bandmate Lance Bass’ podcast, “The Daily Popcast,” and reflected on the all-denim red carpet moment, telling Bass, “You do a lot of things when you’re young and in love.”

Jan. 28, 2001 — Spears and Timberlake do Super Bowl halftime

The 2001 Super Bowl halftime show was a star-studded affair with Spears performing alongside Timberlake and his 'N Sync bandmates and Aerosmith, Nelly and Mary J. Blige.

In 2022, Spears honored the moment with a post on her Instagram

Her post featured a clip of her performance as she sang "Walk This Way." Justin can be seen towards the end of the clip.

July 29, 2001 — At a match, ‘Pinky’ and ‘Stinky’ match

When 'N Sync threw its third annual Challenge for the Children charity event in July 2001, Spears was right by Timberlake’s side. The event included an all-stars celebrity basketball match. Spears and Timberlake continued with their matchy-matchy love in matching jerseys with their pet names for one another (“Stinky” and “Pinky”) on the back.

According to a 2014 Billboard story that reflected on Spears’ 2002 interview with Oprah, the singer explained the origins of the nicknames.

“I have a ring that he gave me that I wear on my pinky so he started calling me Pinky, and then I started calling him Stinky for some reason, so that’s our nicknames!” she explained.

September 2001 — Spears and Timberlake at home and in love

In Sept. 2001, Spears was 19 years old when she told the Guardian in an interview that Timberlake lived with her when he was in town.

“I’m not ashamed at all to say that I love him from the bottom of my heart,” she told the outlet. “As far as love is concerned, with him, too much is not enough. He’s everything.”

Feb. 2, 2002 — Live from New York, Spears and Timberlake appear on 'SNL'

While promoting her film “Crossroads,” Spears made her second appearance on “Saturday Night” as the show’s musical guest and host. During her opening monologue, Timberlake appeared alongside her for a cameo.

Feb. 11, 2002 — Spears brings Timberlake to Los Angeles ‘Crossroads’ premiere

In February 2002, Spears starred in the cult-classic girls’ road trip film “Crossroads.” To promote the movie, Timberlake came as her date to the world premiere in Hollywood, California.

March 2002 — Spears confirms she and Timberlake called it quits

Amid intense speculation about their relationship, Spears reportedly said during a London press conference promoting "Crossroads" that she was not in "an intense relationship with anyone at the moment," according to Entertainment Weekly.

A few days later, on March 27, 2002, Spears told Britain's "Big Breakfast" show unequivocally that she was single.

"I’m single… right now," she said in an interview with Richard Bacon.

Nov. 4, 2002 — Timberlake breaks his silence on the breakup

Following their breakup, fans and media alike speculated about what could have caused it.

That year, Timberlake did an interview with Barbara Walters where he alluded that Spears had caused the split.

During a “20/20” special that aired on Nov. 4, 2002, the pop singer spoke to Walters at his family home in Memphis, Tennessee, about his stardom, 'N Sync and break up with Spears.

When prompted by Walters about rumors that Spears had cheated, Timberlake didn’t necessarily bend over backward to deny the claims, despite having told the journalist that he and Spears had agreed to not overtly “say specifically why.”

“We’re not perfect. I don’t judge anybody. It’s just young love. It’s just young love. It was a very intense relationship, that’s for sure,” Timberlake told Waters in response to her questions about Spears’ alleged infidelity.

Timberlake fanned the flames that same year when he released “Cry Me a River” with a music video that included a female actor with Spears’ likeness.

November 2003 — Britney speaks to Diane Sawyer about their breakup

In a tearful “Primetime” interview with Spears, interviewer Diane Sawyer pressed on the dynamic of their breakup and referred to her as “a kind of villain in the tabloids.”

“You broke his heart. You did something that caused him so much pain, so much suffering. What did you do?” Sawyer asked Spears at the time

“I was upset. I was upset for a while ... I think we were both really young, and it was kind of waiting to happen,” Spears said in response. “I will always love him, and he’ll always have a special place in my heart.”

“He left the impression that you weren’t faithful, that you betrayed the relationship,” Sawyer continued.

“I think everyone has a side of their story to make them feel a certain way,” Spears responded. “I’m not technically saying he’s wrong, but I’m not technically saying he’s right either. It was a really weird time ... I just felt exploited and weird.”

Later, in a since-deleted December 2021 Instagram post, Spears would say that though she initially "never talked to anyone" following the split, her former manager had made her speak to Sawyer, E! News reports.

"Something I never shared when I had that big break up years ago was that I couldn’t talk afterwards," she wrote in her post. "I never spoke to anyone for a long time... I was in shock."

June 2021 — Timberlake tweets his support amid the #FreeBritney movement

In 2021, Spears pushed to end her 13-year-long conservatorship. In response, Timberlake told fans on X, then known as the platform Twitter, “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,” Timberlake wrote in his tweet. “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.”

October 2023 — Spears reveals in her memoir that she and Timberlake terminated a pregnancy

In her upcoming book, “The Woman in Me,” Spears revealed that she and Timberlake became pregnant during their relationship and that, ultimately, they made the difficult decision to terminate the pregnancy.

“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,” Spears wrote in an excerpt of her memoir obtained 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.”

“If it had been left up to me alone, I never would have done it,” she continued. “And yet Justin was so sure that he didn’t want to be a father.”

January 2024 - Spears’ fans rally to chart her 2011 track ‘Selfish’ after Timberlake releases a new single called ‘Selfish’

Timberlake revealed Jan. 25 that he is putting out a sixth studio album and released its new single, “Selfish.”

In an attempt to troll Timberlake following Spears’ revelations about their relationship in her memoir, her fans helped her 2011 song called “Selfish” chart on iTunes. By Jan. 26, Spears’ “Selfish” ranked No. 2 while Timberlake’s track of the same named landed at No. 3. (Representatives for Apple, Spears and Timberlake did not respond to NBC News’ request for comment.)

January 2024 - Spears apologizes for ‘some of the things I wrote about in my book’ and praises Timberlake’s new music

On Jan. 29, Spears wrote on her Instagram: “I wanna apologize for some of the things I wrote about in my book. If I offended any of the people I genuinely care about I am deeply sorry … I also wanted to say I am in love with Justin Timberlake’s new song ‘Selfish.’”

She also praised Timberlake’s appearance on “The Tonight Show” with Jimmy Fallon and said his other new track “Sanctified” is “wow.”

This article was originally published on TODAY.com