Britney Spears and Kevin Federline’s Relationship Timeline: From Divorce to Coparenting

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Britney Spears and Kevin Federline's Relationship Timeline: From Divorce to Coparenting

Britney Spears and Kevin Federline have certainly had their ups and downs since splitting in November 2006. The former couple, who tied the knot in 2004 and share sons Sean Preston and Jayden, have gone from feuding exes to supportive coparents. The DJ praised his ex-wife for seeking mental health treatment amid her father Jamie Spears’ illness in April 2019. “Kevin commends Britney for recognizing that she needs to take a step back and that she is taking the reasonable steps to deal with her situation in a responsible way,” Federline’s attorney, Mark Vincent Kaplan, told The Blast. He also agreed to care for their children until she recovered. [jwplayer pI6oLxTO-zhNYySv2] The pair's journey to amicability hasn’t been an easy one, however. Just months prior, the twosome were locked in a bitter feud after Federline requested an increase in child support payments. The duo, who once avoided each other at their son Sean Preston’s baseball game, according to an eyewitness, have also feuded over custody in the past. By 2015, however, they seemed to have temporarily gotten over their differences: The reality star recalled his happier times with Spears to Access Hollywood in March 2015. "It was a good time in my life," he said, adding that their coparenting was going “great.” When Britney challenged her conservatorship in a bombshell hearing six years later, Federline supported his ex-wife in a statement. "The best thing would be for their mom to be healthy and happy," his lawyer Mark Vincent Kaplan said in June 2021. "And if either of those things aren't true, it doesn't provide for the best setting for custody to be exercised. [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." The attorney added at the time: "Britney has not been served well by the conservatorship and it's not consistent with what she wants. I think that she should be able to challenge that. And if it's what's best for her, Kevin supports it. ... "If she's strong and healthy and wants to be in control of her own life, and can do that in a reasonable, responsible fashion, then more power to her." Five months later, Us confirmed that Jamie believes his daughter's conservatorship should end "immediately." Scroll through to relive Britney's ups and downs with the One Tree Hill alum over the years. [podcast_block]

Credit: J.Sciulli/WireImage for Ogilvy Public Relations

Britney Spears and Kevin Federline's Relationship Timeline: From Divorce to Coparenting

Britney Spears and Kevin Federline have certainly had their ups and downs since splitting in November 2006. The former couple, who tied the knot in 2004 and share sons Sean Preston and Jayden, have gone from feuding exes to supportive coparents. The DJ praised his ex-wife for seeking mental health treatment amid her father Jamie Spears’ illness in April 2019. “Kevin commends Britney for recognizing that she needs to take a step back and that she is taking the reasonable steps to deal with her situation in a responsible way,” Federline’s attorney, Mark Vincent Kaplan, told The Blast. He also agreed to care for their children until she recovered. [jwplayer pI6oLxTO-zhNYySv2] The pair's journey to amicability hasn’t been an easy one, however. Just months prior, the twosome were locked in a bitter feud after Federline requested an increase in child support payments. The duo, who once avoided each other at their son Sean Preston’s baseball game, according to an eyewitness, have also feuded over custody in the past. By 2015, however, they seemed to have temporarily gotten over their differences: The reality star recalled his happier times with Spears to Access Hollywood in March 2015. "It was a good time in my life," he said, adding that their coparenting was going “great.” When Britney challenged her conservatorship in a bombshell hearing six years later, Federline supported his ex-wife in a statement. "The best thing would be for their mom to be healthy and happy," his lawyer Mark Vincent Kaplan said in June 2021. "And if either of those things aren't true, it doesn't provide for the best setting for custody to be exercised. [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." The attorney added at the time: "Britney has not been served well by the conservatorship and it's not consistent with what she wants. I think that she should be able to challenge that. And if it's what's best for her, Kevin supports it. ... "If she's strong and healthy and wants to be in control of her own life, and can do that in a reasonable, responsible fashion, then more power to her." Five months later, Us confirmed that Jamie believes his daughter's conservatorship should end "immediately." Scroll through to relive Britney's ups and downs with the One Tree Hill alum over the years. [podcast_block]

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November 2006

Things ended between the duo when the Crossroads star filed for divorce in November 2006, citing “irreconcilable differences.” In her initial filing, Spears asked for legal and physical custody of her two sons, with Federline to receive “reasonable visitation rights.”

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March 2007

Four months later, the pair reached a settlement. A statement was issued by Federline’s former lawyer, Michael Sands: “The parties signed an agreement which was a global settlement on all issues of their marriage and child custody.”

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July 2007

The one-time couple’s divorce was finalized in July 2007, with the parents planning to share equal custody at the time.

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January 2008

Federline was awarded sole custody of Preston and Jayden in 2008 after Spears experienced a mental breakdown that resulted in her being placed on a 5150 psychiatric hold. In June 2008, they agreed to a settlement in which Federline retained sole custody of their boys, while Spears would receive two visits and one overnight per week.

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March 2011

The former pair were not on speaking terms in March 2011, attending their son Preston’s little league game separately and avoiding one another. “They kept their distance from one another and didn't speak,” an onlooker revealed at the time.

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March 2013

It was a different story by March 2013: The “Hold It Against Me” singer not only joined Federline to cheer their sons on at a soccer game, but also hung out with his then-girlfriend (now wife) Victoria Prince.

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November 2013

The Celebrity Fit Club alum made an effort to get along with Spears’ then-boyfriend David Lucado at one of Preston and Jayden’s soccer games. Federline also addressed any would-be awkwardness to TMZ, saying, “Nah, man. You know, everybody's moved on."

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March 2015

K-Fed talked coparenting with the Princess of Pop to Access Hollywood Live in March 2015. "We have two beautiful children. The way that everything has turned out, everybody's happy. Coparenting is going great. I can't complain."

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June 2015

The model remembered his relationship with the Vegas performer fondly in June 2015, telling Us, “That time of my life, it was great. It was fun, it was crazy, it was chaos…The limelight, the entertainment business, the lifestyle — period.” He also called his former spouse a “loving, caring person,” adding, “There was ups and downs. We’re not perfect people, obviously. There’s things that she did, there’s things that I did…I think all of that is just from being young and everything plays a part into it…[but] I have so many great memories, they outweigh the bad. For us to split up and me say that, it should speak very loudly.”

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May 2016

The exes almost looked like friends while chatting it up at their sons’ football game, smiling and sharing secrets: An onlooker said the pop star whispered something in Federline’s ear at one point as they cheered their boys on from the sidelines.

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June 2017

The former backup dancer talked about the progression of his relationship with Spears to Bravo in June 2017. “It wasn’t always easy, but it’s a lot easier now,” he told the outlet. “When you are coparenting, you have to be willing to give up some of the things you would really like to do.”

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February 2018

Things took a turn for the worse once more in February 2018, when the DJ requested an increase of $20,000 a month in child support payments. “She’s angry Kevin is asking for more money because she pays for everything,” a source told Us at the time, noting that their relationship was “strained.”

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March 2018

Federline “flatly rejected” the former Mouseketeer’s initial child support proposal, instead asking that she double his payments to nearly $40K. According to a source, Spears’ camp deemed the move a “money grab:” “Kevin hasn’t had a full-time job in a long time. He just continues to sponge off Britney. She absolutely will not allow Kevin to take advantage of her. If he even dares to withhold her kids from her after asking for a child support increase, there will be hell to pay.”

Credit: Courtesy of Britney Spears/Instagram

May 2018

Retaliation was a worry for the “Piece of Me” singer amid the couple’s child support feud: “Britney is extremely agitated and extremely concerned that Kevin is going to no longer allow her to see their children because he has sole custody as retribution for not agreeing to the $40,000 in child support payment, which would be a $20,000 increase from what he is getting now,” a source told Us. 

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June 2018

It appeared Britney didn't need to worry: Federline allowed the songstress to take their kids on her Piece of Me U.S. tour amid their ongoing custody battle. “He knows it’s better for her when they’re on the road with her,” a source told Us. “Even though Kevin and Britney are locked in a bitter dispute, he is keeping that completely separate from what is best for the boys, which he recognizes is being with their mom.”

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September 2018

After months of back and forth, the couple’s drawn-out custody battle finally came to an end, with a settlement reached between the two parties in September. The agreement saw Britney increase her payments for her sons from $20,000 to roughly $35,000 a month. A source told Us that the deal “allows Kevin to give the boys a similar lifestyle [to the one] they have when they are with Britney.”

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December 2019

“Britney does not have much of a relationship with Kevin other than everyday coparenting stuff,” a source told Us in December 2019 about the exes. “They’re cordial but don’t do very much as a family.”

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April 2019

The “Caught Up” rapper stepped up to take care of Sean Preston and Jayden while Britney sought voluntary mental health treatment at a wellness center. “Kevin commends Britney for recognizing that she needs to take a step back and that she is taking the reasonable steps to deal with her situation in a responsible way,” Vincent Kaplan, told The Blast.

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August 2019

The former couple made a change to their custody agreement on August 28, a source confirmed to Us. The adjustment gave Federline 70 percent custodial rights and Spears 30 percent.

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March 2020

The singer revealed on social media that she was thinking of removing a matching dice tattoo that she got with Federline **in 2004 during a trip to Ireland.

“Albert Einstein once said 'God does not play dice with the universe' …. so maybe I shouldn’t have gotten the pink dice 7 on my left arm 🎲🎲 !!!!! I don’t even like ink …. guess I should remove it ?!?!!!!” Spears asked her followers via Instagram in March 2020.

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June 2021

Following Spears' testimony during her conservatorship hearing, Federline’s lawyer Mark Vincent Kaplan said in a statement that the rapper “only hopes [for] the best for her because when the best for her is achieved, it's the best for their kids.”

Kaplan continued, "The best thing would be for their mom to be healthy and happy. And if either of those things aren't true, it doesn't provide for the best setting for custody to be exercised.”

Credit: Courtesy of Britney Spears/Instagram

April 2022

In April 2022, Spears took to social media to announce that she was expecting her third child.

“Kevin is aware of Britney’s Instagram post,” Federline's attorney, Mark Vincent Kaplan, told NBC News at the time. “He wishes her the best for a happy, healthy pregnancy and congratulates her and [fiancé] Sam Asghari as they plan for the excitement of parenthood together.”

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August 2022

Federline alleged in an August interview with the Daily Mail that his two sons with the pop star chose not to attend her June wedding to Asghari but were “happy” for her. Federline also claimed that Sean Preston and Jayden James “struggled” with her often revealing Instagram posts.

The Iran native, for his part, slammed his wife’s ex in an Instagram Story statement. He wrote: “There is not validity to his statement regarding the kids distancing themselves and it is irresponsible to make that statement publicly. 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.”

Britney was equally “saddened” by her former spouse’s comments in her own Instagram message. “As we all know, raising teenage boys is never easy for anyone,” she noted. “It concerns me the fact that the reason is based on my Instagram … it was LONG before Instagram … I gave them everything.”

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September 2022

Jayden spoke out about the estrangement from his mom in a bombshell interview with the Daily Mail. “I think Mom has struggled giving us both attention and showing us equal love and I don’t think she showed enough to Preston and I feel really bad for that,” he shared, referring to his older brother. “We’ve both been through so much pressure in the past that this is our safe place now, to process all the emotional trauma we’ve been through to heal, heal our mental state.”

The teen added: “If I complained, she went after [my brother]. I feel guilty, so I am there for him. Mom has treated me better.”

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September 2022

“I was mortified for her. I really was. I still feel bad," Federline said of his ex-wife's conservatorship in his tell-all 60 Minutes Australia interview, adding that the reason he couldn't help her was because of "the boys, the boys, the boys. I had to worry about them. I couldn’t get involved.”

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September 2022

While Britney slammed Kevin for his comments in the 60 Minutes interview, she also got real with her sons. “I helped your father who hasn’t had a job in 15 years. … I assume it is easier for you guys not to have someone check on you to make sure you’re doing your homework,” she alleged in response. “I’m sure ... your dad smoking weed every day benefits your daily life at 15 and 16 to partake in a VERY COOL GENERATION.”

Days later, the pop star took to Instagram to share a since-deleted message about her emotions regarding her children's estrangement from her. “Since they’ve been gone, I’ve honestly felt like a huge part of me has died,” she said. “Like, literally, I have no purpose anymore. They were my joy, they were my everything. I looked forward to seeing them. That was what I lived for.”

Britney ended the audio on a hopeful note, however, directing her love to her boys and wishing them a happy birthday.