A Timeline Of Every Britney Spears Marriage And Divorce Explained

Britney Spears and Sam Asghari are officially parting ways. This will be the first divorce for the 29-year-old fitness mogul/model, but Spears has already gone through two divorces. Spears' love life has been filled with chaos since 2022. The Grammy winner's seemingly perfect relationship with Justin Timberlake ended in 2002, inspiring his breakup anthem "Cry Me A River." Spears received the brunt of the public backlash due to rumors of her unfaithfulness to JT. However, their split trended for so long that fans eventually noticed Timberlake's habit of tearing Spears down when it served him. Despite taking a hit to his reputation, Timberlake has come out better romantically — even if he and wife Jessica Biel almost didn't make it.

Unfortunately, Spears' experienced some rough relationships after parting ways with Timberlake. Since 2002, Spears has been married three times. Two of those marriages ended in divorce. One of her exes fathered Spears' kids and introduced a whole array of drama into her life that's continued to this day. Meanwhile, one ex-husband crashed her wedding to another partner. What's more interesting is that most of these relationships happened during her controversial conservatorship, which further complicated things. Here's a complete timeline of Spears' marriages and divorces.

Jason Alexander was Britney Spears' first husband

Britney Spears and Jason Alexander weren't wed long enough to have a destination honeymoon, but the wedding still counted! According to ABC, Spears and Alexander — who knew each other long before Spears hit it big — decided to elope in January 2004. However, the marriage lasted barely two days —55 hours to be exact — before Spears reps got things annulled. During the interview with ABC, Alexander claimed that Spears cheated on Justin Timberlake with him. He also expressed regret over not fighting to have their marriage honored, which explains why he showed up uninvited to Spears's June 2022 wedding to her third husband, Sam Asghari.

According to TMZ, Alexander caused all kinds of chaos after arriving at Spears' home and attempting to make contact with her. Eventually, someone called the police, and Alexander was arrested for an unrelated offense. Spears' lawyer Matthew Rosengart condemned Alexander's behavior in a statement. "I am personally working with the sheriff's department to ensure Mr. Alexander is aggressively prosecuted to the fullest extent of the law," he said. During an appearance on the "One Degree of Scandalous" podcast, Alexander shared that he'd spoken to Spears days prior and implied that he showed up at the wedding to come to Spears' defense, "Maybe I wasn't on the f**king guest list," said Alexander. "I came in through the f**king back. Either way, this is Britney's wedding day, and she's locked in her f**king bedroom," he added.

Then came Kevin Federline

It seems that Britney Spears made it out of her marriage to Jason Alexander without too much long-lasting drama. But what about her relationship with Kevin Federline? That same year, Spears tied the knot with Federline, who at the time was a famous background dancer. According to Today, they had a small wedding at Spear's home in September of 2004. However, they didn't file their paperwork until two months later. The couple had two sons: Sean Preston and Jayden James Federline. 

Their marriage was largely unpopular with fans due to rumors of Federline leeching off of and cheating on the singer. The fact that actor Shar Jackson, mother to his two oldest kids, claimed that he'd cheated on her with Spears didn't help. "He cheated, he lied, he left," Jackson shared with MTV News in 2005. "There you go, in that order: Cheated, lied, left. And that's it. It's cool, though. Everything happens for a reason." During this time, the media was full of reports about Spears' mental health battle, much of which centered on her fitness as a mom. Unfortunately, their relationship didn't survive long after their youngest son, Jayden, was born.

Britney Spears filed to divorce Kevin Federline

Britney Spears made the decision to end her marriage. According to People, Spears filed to divorce Kevin Federline in 2006 while her youngest was still an infant. Spears' loved ones apparently supported her decision. "It's about time," shared a Spears' insider. "During the whole pregnancy they had problems. She tried to support him as much as she could, but at the end of the day she realized it wasn't best for her and her children [to stay]. She's standing up for herself and making positive changes in her life," they added.

Unfortunately, Spears and Federline's split only led to more stress for the pop star. Since their initial divorce, the couple has returned to court several times — mostly regarding custody of their kids, who are now teenagers. They've also fought over money, usually because Federline, who has primary custody of the boys, has requested more child support, per E! News. Federline has also been super vocal about Spears' troubled history, though he rarely acknowledges the possibility that their relationship may have contributed to her downfall. He has, however, denied that he's moving their kids to Hawaii so that he can continue drawing child support from his ex-wife, according to Page Six.

Was Sam Asghari Britney Spears' true love?

Britney Spears and Sam Asghari had been together for many years, but their June 2022 wedding qualifies the two as newlyweds. According to NPR, Asghari's publicist supplied them with a statement. "I am very ecstatic this day has come, and they are married," said Brandon Cohen. "I know he wanted this for so long. He is so caring and supportive every step of the way." After the ceremony, Spears posted their first official wedding photos to Instagram. "Wow !!! Holy holy crap !!! WE DID IT !!! WE GOT MARRIED !!! Gggggeeeeezzzzz !!! It was the most spectacular day !!!" Spears captioned the post. "I had a panic attack and then got it together ... the crew who created our home into literally a dream castle were fantastic !!! The ceremony was a dream and the party was even better. 

In addition to Spears' ex-husband Jason Alexander, Selena Gomez, Madonna, and Paris Hilton were among the celebrity guests, based on the tags in her post. While the couple never dealt with quite as many scandals as Spears faced with her past suitors, they still faced negative rumors, such as death hoaxes and general debate over whether Spears was in the best company, after a judge freed her from her decade-plus conservatorship.

Britney Spears and Sam Asghari have separated

It looks like Britney Spears and Sam Asghari's marriage is over. On August 16, TMZ reported that the couple were separating. This news came a week after Asghari reportedly found out that Spears cheated on him and initiated an argument. "It's only a matter of time before Sam files for divorce," shared a source with the outlet. Unfortunately, their marriage appears to actually be ending.

Hours later, Ashghari officially filed for divorce, according to ET. Although Spears hasn't addressed their impending divorce, a source close to her shared a supportive statement. "[Britney] has been denying any cheating allegations and going through a lot of emotions," shared the source. "She is hurt because the situation brings up old feelings for her. This is the last thing she needed, especially after her boys moved to Hawaii, being worried about the fires there, and so on." They continued, "She has been trying to get back on her feet and be healthy emotionally, physically, and mentally. Britney has people by her side and her immediate circle is there for her. They are rallying around her."