Your tip
Your tip
RadarOnlineRadarOnline
or
Sign in with lockrMail

Britney Spears and Kevin Federline's Explosive Relationship Timeline Revealed After Rapper Goes Off on Ex in Controversial Memoir

Photo of Britney Spears, Kevin Federline
Source: MEGA

Britney Spears and Kevin Federline's relationship has seen plenty of dark days.

Nov. 26 2025, Published 8:30 p.m. ET

Britney Spears and Kevin Federline's relationship has seen more downs than ups, especially since parting ways.

RadarOnline.com can reveal details of their relationship, from tying the knot to taking shots at one another in their respective memoirs.

Article continues below advertisement

2004: Britney Spears and Kevin Federline Meet

Photo of Britney Spears, Kevin Federline
Source: MEGA

Britney Spears and Kevin Federline were married for nearly three years.

Spears found love again when she met Justin Timberlake's former backup dancer, Federline, in the summer of 2004.

In a 2008 interview, Federline said they "hit it off right away" after their eyes met while at a club in Hollywood.

"I was madly in love with her. Everything just seemed so right. I didn't see it as too fast or too slow," he recalled. The DJ also wrote about their meet-cute in his memoir, You Thought You Knew.

"We talked for a little while and then hit the dance floor," he shared. "Nothing too wild, just a little playful back and forth. Honestly, at the time, in my 25-year-old mind, I was just thinking about smashing that."

He then detailed their "very passionate, very intense" first hookup, which occurred while he was still with his then-pregnant fiancée, Shar Jackson.

Article continues below advertisement

September 2004: Britney Spears and Kevin Federline Get Married

Photo of Britney Spears, Kevin Federline
Source: MEGA

Britney Spears and Kevin Federline tied the knot a few months after their meeting.

Nearly three months after they began dating, Spears and Federline exchanged vows in California in September 2004.

During a 2005 interview with Ellen DeGeneres, the Toxic singer said she was the one who proposed to Federline.

"Actually, I was a little rejected at first. I kind of got slapped down," she recalled.

Her sentiment echoed Federline's account, which said they discussed getting engaged after the European leg of her tour.

"There we were, sitting in first class, sipping cocktails, talking about life, and then, bam, she was casually, or maybe not so casually, proposing to me," he writes. "I kind of laughed it off, played it cool, and told her no."

Article continues below advertisement

September 14, 2005: Britney Spears and Kevin Federline Welcome Their First Child Together

Photo of Britney Spears, Kevin Federline
Source: MEGA

Britney Spears and Kevin Federline share two children.

Spears and Federline became first-time parents when they welcomed their first child, Sean Preston, on September 14, 2005.

Article continues below advertisement

September 12, 2006: Britney Spears and Kevin Federline's Second Child Is Born

Photo of Britney Spears, Kevin Federline
Source: @britneyspears/Instagram

Britney Spears and Kevin Federline separated a few months after the birth of their second child.

Spears and Federline's second son, Jayden James, was born on September 12, 2006, at Cedars-Sinai Medical Center in Los Angeles.

Article continues below advertisement

November 7, 2006: Britney Spears Files for Divorce From Kevin Federline

Photo of Britney Spears, Kevin Federline
Source: MEGA

Britney Spears and Kevin Federline both remarried after their divorce.

Two months after they expanded their family, Spears filed for divorce from Federline, citing irreconcilable differences.

According to the dancer, he learned about his then-wife's filing while he was promoting his album Playing With Fire in Canada.

"I got to the studio, went through the usual motions with producers," he details in his memoir. "I knew what to expect, another day answering the same questions, until a producer ambushed me – right before I went live on air – with, 'How do you feel about Britney filing for divorce?' My brain just…froze."

Article continues below advertisement

March 2007: Britney Spears and Kevin Federline Reach an Initial Divorce Settlement

Photo of Britney Spears, Kevin Federline
Source: MEGA

Britney Spears and Kevin Federline engaged in a custody battle after finalizing their divorce.

In March 2007, the exes reached an initial divorce settlement, which included a custody agreement.

"The parties signed a global settlement on all issues of their marriage and the custody of the children," a spokesperson for Federline's attorney said.

Article continues below advertisement

July 2007: Britney Spears and Kevin Federline Finalize Their Divorce

Photo of Britney Spears, Kevin Federline
Source: MEGA

Britney Spears and Kevin Federline agreed to a new custody arrangement in 2019.

Spears and Federline agreed to share custody of their sons when they finalized their divorce in July 2007.

"I think she's okay with the terms," Spears's lawyer, Laura Wasser, said at the time. "I think both of them would prefer to have more custody, and that can be worked out down the line."

Article continues below advertisement

December 2008: Kevin Federline Reflects on Co-Parenting With Britney Spears

Photo of Britney Spears, Kevin Federline
Source: MEGA

Britney Spears and Kevin Federline began co-parenting after their split.

Although they officially ended their marriage, Spears and Federline continued co-parenting their children.

"Britney is an awesome mom. That's one thing I never really have to worry about," he told People in 2008.

He added: "It's good for the kids to see that Daddy does care about Mommy, and Mommy does care about Daddy."

However, they later engaged in a long custody battle that gave Federline sole physical and legal custody of their children amid Spears' controversies.

In 2019, they reached a new arrangement that granted Spears 30 percent of unsupervised custodial rights.

Article continues below advertisement

2022: Britney Spears and Kevin Federline's Feud Begins

READ MORE ON Celebrity
Photo of Britney Spears, Kevin Federline
Source: MEGA

Kevin Federline spoke about Britney Spears' estrangement from their two sons.

Radar Logo

Never Miss an

Exclusive

Daily updates from the heart of Hollywood, right to your inbox

By entering your email and clicking Sign Up, you’re agreeing to let us send you customized marketing messages about us and our advertising partners. You are also agreeing to our Terms of Service and Privacy Policy.

Things took a turn when the A League of My Own crooner discussed his ex-wife's relationship with their children.

"The boys have decided they are not seeing her right now. It's been a few months since they've seen her. They made the decision not to go to her wedding," he told ITV, referring to the …Baby One More Time singer's marriage to Sam Asghari.

Spears took to Instagram to respond to her ex-husband's bombshell, writing, "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 fact that the reason is based on my Instagram ... it was LONG before Instagram ... I gave them everything. Only one word: HURTFUL ... l'Il say it ... My mother told me, 'You should GIVE them to their dad.' I'm sharing this because I can. Have a good day folks!"

Article continues below advertisement

2023: Britney Spears Writes About Kevin Federline in Her Memoir

Photo of Britney Spears, Kevin Federline
Source: MEGA

Britney Spears released her memoir in 2023.

On October 24, 2023, Spears published her memoir, The Woman in Me, in which she looked back at her marriage to Federline and her public breakdown after their divorce.

In one part, she opened up about the January 2008 incident that led her to be put on a 72-hour psychiatric hold.

"I just couldn't let him go. I didn't want anyone taking my baby," she says of her then-16-month-old son Jayden. "Before I knew what was happening, a SWAT team in black suits burst through the bathroom door as if I'd hurt someone."

Article continues below advertisement

2025: Kevin Federline Releases His Memoir; Britney Spears Responds

Photo of Britney Spears, Kevin Federline
Source: MEGA

Kevin Federline released his first-ever memoir on October 21.

On October 21, Federline released his first-ever tell-all, You Thought You Knew, which included shocking allegations against Spears.

The Criminal singer responded to the claims in a statement, writing, "I 100 percent beg to differ the way he is literally attacking me in his interviews. If truth be told the man in the interview went STRAIGHT TO the SOURCE and said it CLEAR AS DAY … no money from Britney for 5 years you trying to get paid that's what general America is saying weird you both have moved on… your kids are adults it's a different world now … why is HE SO ANGRY … and what's scary is he's convincing."

Spears shared another lengthy post on X, accusing Federline of profiting off her pain.

© Copyright 2025 RADAR ONLINE™️. A DIVISION OF MYSTIFY ENTERTAINMENT NETWORK INC. RADAR ONLINE is a registered trademark. All rights reserved. Registration on or use of this site constitutes acceptance of our Terms of Service, Privacy Policy and Cookies Policy. People may receive compensation for some links to products and services. Offers may be subject to change without notice.