Britney Spears and Kevin Federline's Relationship Timeline

The former couple were married for three years, and share sons Sean Preston and Jayden James

Take a look back at Britney Spears and Kevin Federline's time together.

The pop superstar and former backup dancer met during the summer of 2004 and tied the knot later that year. During their time together, they welcomed two children, sons Sean Preston and Jayden James.

Spears and Federline divorced in July 2007, and have had several different custody arrangements since, with Federline having majority custody for many years.

In May 2023, Spears "consented" to her sons moving to Hawaii with Federline, his attorney Mark Vincent Kaplan told PEOPLE: "It's an opportunity for Kevin and his wife, and the boys are ready to get away from the L.A. microscope."

From when they first met to their relationship over the years, here's a look at Spears and Federline's history.

Related: All About Britney Spears and Kevin Federline's 2 Kids

Summer 2004: Britney Spears and Kevin Federline meet

Spears and Federline, who was formerly a backup dancer for Justin Timberlake, met in 2004 at a club in Hollywood called Joseph's.

“Our eyes met and that was it. We just hit it off right away,” Federline told PEOPLE in 2008. “I was madly in love with her. Everything just seemed so right. I didn’t see it as too fast or too slow.”

September 2004: Britney Spears and Kevin Federline get married

In September 2004, nearly three months after they first began dating, Spears, then 22, and Federline, then 26, tied the knot at an event billed as an engagement party in Studio City, California.

Although the couple had originally planned on getting married the following month in a lavish ceremony, they ended up scrapping the idea in favor of the surprise.

“I just thought it would be too much if we had done it when we were supposed to,” Spears told PEOPLE at the time. “It became this huge thing and I was like, ‘What are we waiting for? We know this is the real thing, why not just do it now?’ That’s why I wanted to sneak and do it our little way.”

Related: Kevin Federline's 6 Children: Everything to Know

September 14, 2005: Britney Spears and Kevin Federline have first child together

One month after their wedding, the singer announced she was taking a break from her career to start a family. Spears and Federline welcomed their firstborn, Sean Preston, on Sept. 14, 2005 (just four days short of their wedding anniversary!), in Santa Monica, California.

"We are ecstatic to announce the birth of our son!" Spears wrote of her son on her website. "Everyone is happy, healthy and doing wonderful. Thank you for all your love and well wishes!"

September 12, 2006: Britney Spears and Kevin Federline have second child together

One year later, Spears and Federline welcomed their second son, Jayden James, together on Sept. 12, 2006. Jayden was born at 1:11 a.m. at Cedars-Sinai Medical Center in L.A.

"Everything is great," Spears' dad Jamie told Access Hollywood after Jayden was born. Two months later, however, Spears filed for divorce.

November 7, 2006: Britney Spears files for divorce from Kevin Federline

After three years of marriage, Spears filed for divorce from Federline in November 2006. She cited irreconcilable differences.

Days before the divorce announcement, Federline hinted at some difficulties in their marriage, saying in part, "Having two kids and trying to do all the business and everything, it’s not easy. It’s tough but we will make it through this. We’re a superpower.”

March 2007: Britney Spears and Kevin Federline reach initial divorce settlement

In March 2007, Spears and Federline reached an initial divorce settlement, which continued their interim arrangement of joint legal and physical custody of their children.

Related: Britney Spears Reveals She Had an Abortion Because Justin Timberlake 'Didn't Want to Be a Father' (Exclusive)

July 2007: Britney Spears and Kevin Federline's divorce is finalized

Spears and Federline's divorce was finalized in July 2007; the two agreed to share custody of their sons. Around the same time, the singer faced mental health issues and two involuntary hospitalizations, resulting in a court-ordered conservatorship managed by her father.

December 2008: Kevin Federline speaks out about custody and co-parenting

Although the couple’s divorce was finalized in July 2007, parenting arrangements evolved as Spears navigated life under the conservatorship — but Federline and Spears amicably co-parented for years.

“Britney is an awesome mom. That’s one thing I never really have to worry about,” Federline told PEOPLE in 2008, adding that while the pair only see each other once in a while, “it’s good for the kids to see that Daddy does care about Mommy, and Mommy does care about Daddy.”

March 2013: Britney Spears and Kevin Federline go to sons' soccer game

Spears and Federline were spotted out alongside each other while watching their sons Sean Preston and Jayden James play soccer in March 2013. The singer was joined by a friend, while Federline was at the park with Victoria Prince, who he later married in August 2013.

2015: Kevin Federline reflects on relationship with Britney Spears

In 2015, Federline told Canada’s etalk that “time” was the secret for their friendly relationship. “It’s been a long, long journey, but I think where both of us are now, we both have somebody else we’re happy [with]. Everything just works.”

May 2018: Kevin Federline asks for more child support

In 2018, Federline began fighting for significantly more child support than he had been receiving over the years. According to court documents filed that May, Federline claimed he makes less than one percent of what Spears does.

“We think the reasonable needs for the children while they would be in Kevin’s custody is probably three times what he’s currently receiving,” Federline’s attorney Kaplan previously told PEOPLE.

After months of court discussions, Spears agreed to increase the amount of Federline's child support.

Related: Britney Spears Reveals Why She Shaved Off Her Hair and Was 'Acting Out' in 2007 (Exclusive)

September 2019: Britney Spears and Kevin Federline negotiate new custody arrangement

Kaplan confirmed to PEOPLE at the time that Spears and Federline came to a new child custody arrangement which gave Spears 10 percent of custodial rights and Federline 90 percent.

June 2021: Kevin Federline's lawyer shares with PEOPLE a statement on Britney Spears' conservatorship

Speaking to PEOPLE, Federline's attorney Kaplan shared Federline's thoughts regarding Spears' emotional testimony about her conservatorship in a Los Angeles court in June 2021.

Referring to Jayden James and Sean Preston, Kaplan said, "[Kevin] certainly respects Britney and only hopes the best for her because when the best for her is achieved, it's the best for their kids. The kids love their mother and he wants there to be a healthy and strong relationship."

August 6, 2022: Britney Spears and Sam Asghari respond to Kevin Federline's claims that her sons don't want to see her

Spears and her then-husband Asghari responded to her ex-husband Federline's comments to The Daily Mail, in which he claimed that his two sons with Spears were choosing not to see her. Spears shot back with an Instagram story saying, "It saddens me to hear that my ex-husband has decided to discuss the relationship between me and my children."

"As we all know, raising teenage boys is never easy for anyone. It concerns me the reason is based on my Instagram. It was LONG before Instagram," she continued, referring to Federline's comment that her social media posts were affecting her children.

Spears added, "Only one word: HURTFUL."

Asghari supported his wife with his own Instagram Story. "There is no validity to his statement regarding the kids distancing themselves and it is irresponsible to make that statement publicly," he wrote. "The boys are very smart and will be 18 soon to make their own decisions and may eventually realize the 'tough' part was having a father who hasn't worked much in over 15 years as a role model."

He added that he doesn't know Federline personally, but he has "nothing against him aside from him choosing to vilify my wife."

In a second Instagram Story, Asghari wrote, "I wish him the best and hope he has a more positive outlook in the future for benefit of all involved." He added, "But for now: Keep my wife's name.....out your mouth."

August 6, 2022: Kevin Federline defends Britney Spears' father

In an interview with The Daily Mail, Federline said that he believes the conservatorship that Britney was put under by her father "saved" her. However, he admitted it had been hard to watch the drama surrounding the years-long legal arrangement that ended in November 2021.

"This whole thing has been hard to watch, harder to live through, harder to watch my boys go through than anything else," he explained. 'It's been tough. It's the most challenging thing I've ever had to do in my life."

"I saw this man that really cared, and really cares about his family and wanting everything to be okay," Federline continued. 'When Jamie took over [the convervatorship], things got into order. He saved her life."

Related: Britney Spears Debuts a First Look at Her New Memoir with a Cover Story in PEOPLE

May 2023: Britney Spears allows Kevin Federline to move with sons to Hawaii

The singer "consented" to her children Sean Preston and Jayden James moving to Hawaii with their father, Kaplan told PEOPLE. "It's an opportunity for Kevin and his wife, and the boys are ready to get away from the L.A. microscope," he said.

October 2023: Britney Spears gives an update on her co-parenting situation

In an exclusive e-mail interview with PEOPLE ahead of the release of her memoir The Woman in Me, Spears shared that her sons, who live in Hawaii with Federline but are in contact with her, remain a great source of pride.

"Starting a family was my dream come true,” she said. "Being a mom was my dream come true.” 

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