Britney Spears’ explosive memoir, The Woman In Me, is due out on October 24. Based on the snippets shared from the book, the “Mind Your Business” singer isn’t pulling any punches. With a career dating back to the early ’90s, her widely televised legal battle to end her 13-year-long conservatorship which led her to shave her head in 2007, and several high-profile relationships, Spears had plenty to discuss within its pages.

Earlier in the week, thanks to teasers from The Woman In Me, fans learned several heartbreaking incidents that she faced during her young adult love with fellow singer Justin Timberlake. Here’s a timeline of Justin Timberlake and Britney Spears’ up-and-down relationship.

Spears’ memoir The Woman In Me will hit shelves on October 24. Find more information here.

December 1992: Britney Spears & Justin Timberlake Meet For The First Time

During her time on The All-New Mickey Mouse Club, Spears met Timberlake along with a host of other notable industry professionals, including Christina Aguilera, Ryan Gosling, and JC Chasez.

In her forthcoming book, she outlines her time on the cast. “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,” she writes. “‘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.”

She continues, “[Once] at a sleepover, we played Truth Or Dare, and someone dared Justin to kiss me. A Janet Jackson song played in the background as he leaned in and kissed me.”

1998: Spears Opens For NSYNC’s Tour

It is unclear if the pair stayed in touch following their time on The All-New Mickey Mouse Club, but in 1998, they reunited on the road. By this time, Timberlake was a member of the boy band NYSYNC, while Spears stepped out as a solo artist. To promote her breakout debut album, …Baby One More Time, Spears joined the group on tour as their official opening support.

1999: Britney Spears & Justin Timberlake Begin Dating

At the time, both parties denied their budding relationship, but in 2001, Spears confessed to Rich and Famous’ Andi Peters that she began dating Timberlake in 1999. She confirmed that their romance began on the road during their 1998-1999 time on tour.

September 7, 2000: Britney Spears & Justin Timberlake Go Public

The pair decided to let the world in on their romance by taking their relationship public. On September 7, 2000, Spears and Timberlake walked the red carpet of the 2000 MTV Video Music Awards hand-in-hand. The world was immediately thrown into a frenzy, and pop music relationships would never be the same.

January 8, 2001: Britney Spears and Justin Timberlake’s Infamously Match Denim Outfits

By the following year, the two wouldn’t be seen without the other. On January 8, 2001, Spears and Timberlake made matching denim outfits (often referred to as a Canadian tuxedo thanks to Bing Crosby) a forever fixture in pop culture. The couple’s American Music Awards wardrobe has been replicated dozens of times by other musicians.

September 2001: Britney Spears & Justin Timberlake Move In Together

In September 2001, things continued to heat up for Spears and Timberlake. While doing press, Spears revealed that he would stay with her whenever Timberlake was visiting Los Angeles. Essentially, the couple had moved in together.

“I’m not ashamed at all to say that I love him from the bottom of my heart,” Spears told The Guardian. “As far as love is concerned, too much is not enough with him. He’s everything. But it is a deeper love now than when I was younger. Like, we’ve gone through so much together, and we’ve known each other since we were 12 years old. We know each other inside and out.”

November 2001: Justin Timberlake Writes And Produces A Song on Britney Spears’ Third Album

In their careers, things were also intensifying. Spears began working on her third self-titled album. On the project, Timberlake teamed up with Wade Robson, one of Spears’ former backup dancers, to write and produce the song “What It’s Like to Be Me.” Timberlake’s creative input also included notable background vocals on the record.

March 27, 2002: Britney Spears Admits To Split From Justin Timberlake

According to Entertainment Weekly, on March 25, 2002, during a press conference for Crossroads in London, she denied she and Timberlake had broken up. The week prior, she told MTV the same thing. However, by March 27, 2002, she finally admitted that the couple was no more to the show, Big Breakfast.

“I’m single… right now,” said Spears.

June 14, 2002: Justin Timberlake Addresses Break-Up

During an interview with People, Timberlake told the outlet that he was heartbroken after his split from Spears. This was the start to a long press run where Timberlake would talk about their past relationship.

November 4, 2002: Justin Timberlake Talks About His “Young Love” with Britney Spears

Timberlake attempted to avoid divulging why the pair split. Instead, he told ABC News, “Honestly, I mean, you know, we’re not perfect. I don’t judge anybody. It’s just young love … It was a very intense relationship — that’s for sure,” while promoting his debut solo album, Justified.

November 25, 2002: Justin Timberlake Releases The “Cry Me a River” Music Video With A Britney Spears Look-Alike

The high road Timberlake once took when chatting about his relationship with Spears was long forgotten by the time his debut solo album, Justified, was released. The breakout single, “Cry Me A River,” seemingly poked fun at Spears for the hurt she was experiencing. T

The Timbaland-produced track also hinted that Spears cheated on Timberlake. “You don’t have to say what you did / I already know, I found out from him,” he Timberlake.

August 2003: Britney Spears Responds To Justin Timberlake’s “Cry Me A River” Music Video

During a conversation with Elle UK, Spears addressed Timberlake’s music video for “Cry Me A River.”

“It was hard for me that he was so exploitative,” she said. “Every interview that he did, he was just talking about us in such an open way, and I just felt, ‘Is nothing sacred anymore?’ It was weird. It was … disappointing.”

She continued, “I think I got way too serious, way too young. It’s very healthy to not be in that relationship right now.”

November 2003: Britney Spears Sits Down With Diane Sawyer

In an appearance on Primetime hosted by Diane Sawyer, Spears opened up about her split from Timberlake. “I was upset. I was upset for a while. I think we were both really young, and it was kind of waiting to happen. I will always love him, and he’ll always have a special place in my heart.”

When asked about the cheating allegations, she said, “I think everyone has a side of their story to make them feel a certain way. I’m not technically saying he’s wrong, but I’m not technically saying he’s right either.”

May 10, 2004: Spears Releases The Music Video For “Everytime,” Which Fans Believe Is A Response To “Cry Me a River”

In 2004, during an interview with MTV, Spears shared the inspiration behind the track. “It’s about heartbreak, it’s about your first love, your first true love,” she said. ‘That’s something all people can relate to because you all have that first love that you think you’re going to be with the rest of your life.”

“I may have made it rain / Please, forgive me / My weakness caused you pain / And this song’s my sorry,” sang Spears.

Thanks to her recent revelations, fans now believe that the visual also speaks to the abortion she had while in a relationship with Timberlake.

July 25, 2006: Timberlake Blames Spears For Post-Breakup Media Frenzy.

Timberlake confirmed to GQ, that “Cry Me A River” was about Spears. He went on to blame Spears for the post-breakup media frenzy they’ve both experienced due to how she handled the split.

“I felt like she had a couple of opportunities to just sort of stick up for me, and she didn’t,” said Timberlake. “Which is fine. But at that time, you know, I fought back, and that’s the way I fought back. I used my mind. I came up with a song.”

The interview was centered around Timberlake’s 2006 album, FutureSex/LoveSounds. The project featured the track “What Goes Around… Comes Around,” another song fans believe was aimed at Spears.

February 12, 2021: Justin Timberlake Issues A Publicly Apology To Britney Spears

The New York Times’ documentary Framing Britney Spears, pushed Spears and Timberlake’s relationship back into the public’s eye. The work aimed to examine Spears’ treatment by the media over her career and how fame impacted her well-being. Fans online began to send angry messages to Timberlake after learning about his treatment of Spears post their break-up.

The backlash prompted Timberlake to issue a public apology to Spears as well as Janet Jackson. “I’ve seen the messages, tags, comments, and concerns, and I want to respond,” wrote Timberlake in a note posted to Instagram. “I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn or did not speak for what was right. I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism. I specifically want to apologize to Britney Spears and Janet Jackson both individually because I care for and respect these women, and I know I failed.”

October 17, 2023: Britney Spears Reveals She Had An Abortion At Justin Timberlake’s Request

Spears is a proud mother of two sons (Sean and Jayden) whom she shares with her ex-husband, Kevin Federline. But a teaser from Spears’ upcoming memoir revealed that her whirlwind romance with Timberlake also resulted in a baby. The excerpt revealed that at the request of Timberlake, Spears terminated the pregnancy.

“It was a surprise, but for me, it wasn’t a tragedy,” Spears penned. “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. 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. To this day, it’s one of the most agonizing things I have ever experienced in my life.”

Posted in: Pop