Britney Spears and Justin Timberlake's Relationship Timeline in 15 Clicks

Britney Spears and Justin Timberlake met on the set of The All-New Mickey Mouse Club in 1992 for the show's 1993 season. They starred alongside Keri Russell, Ryan Gosling, JC Chasez and Christina Aguilera.

In Spears' memoir, The Woman in Me, she revealed the show led them to each other as they connected quickly after their meeting. In fact, she also shared her first kiss with the *NSYNC member during a sleepover.

"A Janet Jackson song was playing in the background as he leaned in and kissed me," she wrote.

Meanwhile, Timberlake told GQ in 2006 that he instantly felt "a spark" upon meeting the Princess of Pop.

"I was in love with her from the start," he revealed. "I was infatuated with her from the moment I saw her."

Spears disclosed in a 2001 interview with Andi Peters that the "Mirrors" singer asked her out when they were doing a radio show before the release of her album ….Baby One More Time in 1999.

"He knocks on the door and he was like, 'Can I see Britney?' And [my assistant] Felicia [Culotta] didn't know who he was and she was like, 'No ... Who are you?' And I was like, 'No! It's Justin!'" she recalled.

The 2001 American Music Awards red carpet became the first event Spears and Timberlake attended together as a couple. They also turned people's heads because of their ensembles, which they came up with.

"We were in New Orleans when Britney and Justin were like, 'We're doing matching denim.' And I was like, 'How are you doing that? Who is doing that?'" fashion designer Steven Gerstein said in a 2020 interview with Jezebel. "Obviously, the Britney/Justin connection added fuel to the fire, but it was really organic ... it was just two kids, wanting to do something cool, and being super cute, matching. It was kind of like their prom."

In her interview with Entertainment Tonight at the Super Bowl Halftime Show backstage, the Crossroads actress spoke about their relationship.

"It's a little hard, but you know what, it's all about trust," Spears said. "He loves me and I love him and we just try to work it out."

To fix their schedules, the pair decided to live together at Spears' Los Angeles home. Although they were already dating for two years at that time, she admitted to feeling the same thing she had during the early days of their relationship.

"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," she told The Guardian.

Entertainment Weekly confirmed in a report that the "If U Seek Amy" singer told the reporters at her press conference in London that she was not in a relationship at that time, suggesting that she and Timberlake called it quits. This mirrored what she said on the Big Breakfast talk show, during which she said she was single.

On the other hand, Spears claimed in her memoir that Timberlake initiated the breakup while working on his first solo album, Justified, and did it via text message.

After Spears broke her silence in public interviews and appearances, Timberlake shared his side and expressed how the split left him with a broken heart.

"It hurts too bad," he told People. "You get to a point when you're crying yourself to sleep every night. I feel like I'm in the middle of a soap opera. I honestly know what it's like to have a broken heart."

Timberlake somewhat dodged the topic of why they broke up in a 20/20 interview with Barbara Walters. He called their relationship a young love "but very intense."

After their breakup, he also released "Cry Me a River," which sparked rumors that Spears cheated on her.

On Primetime, Spears answered the questions that Diane Sawyer threw at her — including a query that painted her as the cause of Timberlake's pain.

"I was upset. I was upset for a while," she responded. "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."

The interviewer hit back and spoke about how the "SexyBack" singer left the impression that she betrayed him by being unfaithful. Spears highlighted that her ex-boyfriend only shared his story and not hers, so she expressed how much she felt exploited at that time.

Following the release of Framing Britney Spears, Timberlake issued a public apology to Spears and Janet Jackson due to his past actions. He infamously exposed the latter's b----- during their performance at the 2004 Super Bowl Halftime Show.

"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," he wrote on Instagram. "I have not been perfect in navigating all of this throughout my career. I know this apology is a first step and doesn't absolve the past. I want to take accountability for my own missteps in all of this."

In another excerpt from the memoir, Spears alleged that Timberlake cheated on her several times throughout their relationship. Reports about his infidelities reemerged, naming several women, including Natalie Appleton, Nicole Appleton, Shaznay Lewis and Melanie Blatt.

The "Sometimes" singer did not name the "celebrity" in the book because she "now has a family" and she "does not want to embarrass" them.

Meanwhile, she also admitted to cheating on Timberlake with Wade Robson.

"[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 wrote.