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Oops she did it again! Britney Spears’ marriage and divorce timeline

The Pop Princess' long history of hit single-digit marriages and chart-topping divorces.

Britney Spears and Sam Asghari

Britney Spears, the former Pop Princess, is quickly on her way to becoming the queen of something else — divorces. Yes, the woman who brought us “Hit Me Baby One More Time” is now hitting us with something else, another divorce announcement. Britney Spears and her husband of one year, Sam Asghari, recently dropped the bombshell that they will be going their separate ways. Unfortunately, this is not the first time Ms. Spears has made such an announcement, in fact, this will be d-i-v-o-r-c-e number three. It can get a little confusing, so we have taken the liberty to recreate her divorce and marriage timelines.

Britney Spears, now 41, first appeared on the scene at the tender age of 16, with her breakout song “…Baby One More Time” on her debut album, also titled ...Baby One More Time. Spears quickly became the teen dream, and an icon for the popular Pop music genre. She debuted her first album in 1998, and the hits just kept on coming. Her songs were always at the top of the charts, and album after album won awards, topped the charts, and cemented her fan base. Then, when she began publicly dating fellow teen star Justin Timberlake of N*Sync, her popularity skyrocketed even higher. Yet, despite all outward appearances of youth, fame, and fortune, Spears’ inner world was beginning to fall apart. No one could have predicted how tumultuous the subsequent years would be for the young starlet. The first hint of trouble came with Spears first marriage, which was brief — very brief.

Jason Alexander-2004

Photo by Chris Farina/Corbis via Getty Images

Jason Alexander and Britney Spears were married for a total of 55 hours. The two decided to tie the knot after a night of heavying partying in Vegas, which they seemed to almost instantly regret. The pair were high school sweethearts, and in fact, Alexander was rumored to be the cause of the split between Spears and Timberlake. In fact, Timberlake wrote a less-than-subtle song titled “What Goes Around… Comes Around” aimed at Spears and her reported infidelity, which was rumored to be with Alexander. Quite the love triangle.

Then in 2004, Alexander and Spears decided on a whim to get married. “We were just being silly,” Spears told ABC News. Spears went on to say the pair only being “silly and rebellious” and had “not been thinking” after a night of partying. The marriage was quickly annulled, and it seemed the romance was short-lived.

…Although possibly not for Alexander. Alexander later claimed to the Daily Mail that the marriage ended under “duress” and that neither he nor Spears wanted it to. He claimed that after almost constant communication between the two, suddenly after the 30-day annulment period, her number was changed, and that was it. He felt it was an indication that Spears was “not in control” of her life even back then, and that the powers that be were already making her decisions for her.

Alexander was later accused of stalking Spears and trespassing on her Thousand Oaks, California home. He even crashed her 20022 wedding to Sam Asghari, knife in hand! Yes, a few short hours before she was to wed current (soon to be ex) Sam Asghari, Alexander came wielding threats and a weapon. He even live-streamed the entire thing, from the break-in to her home, to the confessions of his undying love, saying she was his “first wife and only wife.” Yikes.

Thankfully, Alexander was apprehended and incarcerated, but what a nightmare! Spears was reportedly and understandably very shaken by the event. A restraining order was put in effect that was supposed to keep Alexander at least 100 yards away from Spears at all times. Apparently, at the time of his arrest, he also had other open charges, including embezzlement and possession of stolen property in Ventura County, CA. He is now married to someone else, although still discusses his relationship with Spears and the day of the wedding openly on his Instagram. He was also very outspoken during the time of her conservatorship trials.

As far as Spears went, following the short marriage and heavy partying in 2004, fans began to grow concerned over her increasingly irrational behavior. This mood of apprehension was only heightened with her second marriage in 2004.

Kevin Federline- 2004-2007

With the ink barely dry on her annulment papers, Spears was already signing a new marriage license. Spears married backup dancer Kevin Federline in 2004. The pair met at a Hollywood club and were “inseparable ever since.” After only three months of dating the two got engaged, but by November of 2006, things were already over. In between, the pair had had two sons together, Sean Preston in 2005, and Jayden James in 2006. In fact, the divorce was filed only a few months after they welcomed their second son, Jayden James.

The divorce was finalized in 2007 but in a turn of events, a judge gave Kevin Federline custody of the couple’s two young sons, Jayden James, and Sean Preston. The judge cited Spears’ “habitual, frequent, and continuous use of controlled substances and alcohol” as the cause for the decision.

Shortly thereafter, Spears’ infamous head-shaving, car-window-bashing meltdown occurred, and a conservatorship was put in place, naming her father Jamie Spears as conservator. The conservatorship began in 2008 but was eventually terminated in 2021 after a long and very public court battle.

Federline and Spears’ custody agreement has shifted some over time, however, and now Spears is reportedly estranged from her sons, who live in Hawaii with their father. Although that transition also was not without drama, as old interviews from Kevin Federline were dredged up to create new allegations about Spears. What a mess. Yet eventually all the allegations and unnecessary drama were sorted out, and Federline and his sons are reportedly happy in their new home.

Sam Asghari- 2022-2023

Following the terminated conservatorship ruling, Spears made a big decision and got married for the third time. She expressed that she had wanted to get married again and maybe even have another baby, but that the previous conservatorship agreement prevented this. Now that the conservatorship was lifted, she was free to marry again, which is exactly what she did.

This time, she married her boyfriend of five years, Sam Asghari. Hesam “Sam” Asghari is an Iranian-American model and fitness trainer who is 13 years Spears’ junior. The two met on the set of her music video for “Slumber Party” in 2016, and dated for five years before deciding to get married and tying the knot in 2022.

Asghari alleged that Spears had cheated on him with a number of members of the house staff. He claimed she would ask staff members to film her naked, and that he had reason to believe she was intimate with at least one of them. that A source reported to TMZ that Spears is in a “fragile and hypersexualized state” which is “risky to her own safety.” Asghari also claimed that the two often had physical altercations with Spears being the aggressor, allegedly leaving him with marks, bruises, and a black eye. Paparazzi even captured some of the marks on camera, although their source is still debated.

Yet just as there are two sides to every coin, there are always two sides to every divorce, and Spears has hers. She recently spoke out, saying that “she couldn’t take the pain anymore.” While both posted the typical obligatory celebrity Instagram divorce post saying they “wished each other well” etc., clearly things behind the scenes were not so civil, and Asghari immediately scrubbed Spears from his Instagram. Spears, for her part, has been posting some very explicit photos and videos to her Instagram, which even for her, are quite shocking, fueling the rumors that things are definitely not smooth below the surface.

The pair have no children together, but reportedly do have a prenup which entitles Asghari to $1 million for every two years of marriage, up to $15 million total. Although apparently, that isn’t enough for Asghari as he has allegedly threatened to reveal details of Spears’ private life if the amount doesn’t increase. Asghari’s representatives deny the allegations, but sheesh, can this girl not catch a break?

Spears still has scores of faithful followers, and even Octavia Spencer spoke up for her, reminding the public — and Asghari — that “extortion is illegal.” Which is, indeed, ironic as Spencer was the one who advised Spears to have Asghari “sign a prenup” in a comment on her Instagram. While she deleted the comment and apologized citing it as a joke, it now seems more like a premonition or a prophecy than a joke. Advice that was at least reasonably well followed, it seems.

It has certainly not been an easy road for the pop princess whose ongoing legal battles, divorces, and public struggles seem almost neverending. Yet with this new divorce comes a potential new start for this favorite icon. Perhaps without another person in her life looking to take advantage of her, she can finally begin to heal and who knows, maybe even find a new love! Spears may be the pop princess, but she is also the queen of the comeback, so we are on the edge of our seats to see what she is going to “hit us with” one more time.

Bethany Nicole
About the author

Bethany Nicole

Bethany is an LA based freelance writer and astrologer who specializes in entertainment, relationship and true crime writing. To see more of her work follow her on Instagram @bethanynicolelove.