To people of a certain age, there are few topics as interesting as Britney Spears and her love life. Whilst she never had the talent of someone like Taylor Swift, when she burst onto the scene with her song, Baby One More Time, complete with a music video of her in a school uniform, there were very few people who didn’t know about her. As is so often the case with those that became famous at a young age, Britney struggled with her fame and this manifested in all sorts of weird ways. One of the most consistent throughout her life has been falling in love and marrying far too quickly, as we’ll explore in more detail here.
Jason Allen Alexander – 55 Hours
Having spent her youth dating the likes of Justin Timberlake, Wade Robson and Colin Farrell, it is maybe quite fitting that the first person that Britney Jean Spears chose to marry was a friend from her childhood. It was 2004 and Spears and Alexander were enjoying some partying in Las Vegas when they did what any partying friends would do – they went to the Little White Wedding Chapel and got married. They weren’t the first people to do it and they certainly won’t have been the last, but the fact that Britney was one f the most famous people on the planet at the time means that they might well be the best-known.
When they woke up the following morning, Spears realised that she had made a terrible mistake and petitioned for the marriage to be annulled. The petition stated, “Plaintiff Spears lacked understanding of her actions to the extent that she was incapable of agreeing to the marriage”. The petition was filed at 10.12am in the Clark County Family Court, with Judge Lisa M. Brown signing the order, which was uncontested by Alexander, at 12.24pm. David Chesnoff, Spears’ attorney, said, “There is no marriage now. Jason agreed to this completely. They’ve made a wise decision. I know they care about each other. They are friends.”
The pair got married at around 5.30am on the Saturday, with Chesnoff later declaring that Spears was not intoxicated. It is up to you whether you believe that, of course, although the wedding chapel’s owner, Charlotte Richards, said that they were both sober and that they do not allow ‘anybody who is inebriated’ to get married. “They have to be fully aware of what they are doing”, she said Alexander later said in an interview with Access Hollywood, “It was just crazy, man. We were just looking at each other and said, ‘Let’s do something wild, crazy. Let’s go get married, just for the hell of it.”
In the months and years that followed, any friendship that Spears and Alexander might have had seemed to all but evaporate. When Spears got married for the third time to Sam Asghari, about which we’ll tell you more shortly, Alexander live-streamed himself trying to break into her home. He was stopped by security, with Britney’s former husband claiming that he’d been invited before being physically apprehended and seeing the stream cut out. Spears’ attorney at the time, Mathew Rosengart, said, “I’m working closely with law enforcement to ensure Mr. Alexander is aggressively prosecuted to the fullest extent of the law.”
Kevin Federline – 3 Years
The brief marriage to Jason Allen Alexander happened in the January of 2004. A few months later and the singer headed out on the Onyx Hotel Tour, where one of her backing dancers was a guy called Kevin Federline. Federline had not long broken up with actress Shar Jackson, with whom he had had one child and knew that she was pregnant with their second. There was a plan for Britney to released a reality television series documenting the European leg of the tour, which was scheduled to be called OnTourage. Spears was going to shoot footage of what was happening with her dancers and handlers.
On the 8th of June, however, she fell, injuring her left knee. She underwent arthroscopic surgery the following day, resulting in the European leg of her tour being cancelled and OnTourage along with it. During this time, she had met Federline and the pair had began courting, with Britney announcing in July of 2004 the fact that they were engaged to be married. It had also been confirmed that a reality show detailing their relationship would be broadcast by the United Paramount Network, who had won a ‘fierce bidding war’ for the rights. It would chronicle the relationship between the pair ‘from the earliest stages of their courtship to their engagement and ultimately, their stroll down the aisle’.
Initially titled ‘Britney and Kevin: Can You Handle Our Truth?’, the name was changed to ‘Britney and Kevin: Chaotic’. In episode four, Britney realises that Federline is ‘the one’, asking him to marry her. He says no but then later proposes to her himself. In the final episode of the five episode series, the families of Spears and Federline arrive at what they think is going to be their engagement party, only to be told that they’re actually attending their wedding. Spears faced intense criticism for the series, which people said showed her as a narcissist, with one critic calling it an ‘insult to common sense and decency’.
For her part, Britney later declared the show ‘probably the worst thing I’ve done in my career’. The wedding ceremony took place on the 18th of September, 2004, but they weren’t actually legally married until the 6th of October because of issues with their pre-nuptial agreement. Spears became pregnant with the pair’s first child, giving birth to Sean on the 14th of September, 2005. A little over a year later, on the 12th of September, 2006, she gave birth to Jayden. It is reported that she then told Federline that she wanted a divorce two months after the birth of their second son, citing ‘irreconcilable differences‘.
Spears wanted custody of their two children, waiving any claim of spousal support but saying that each party pay their own legal fees and that certain assets such as ‘miscellaneous jewelry and other personal effects’ get confirmed as separate property. What followed was a contentious custody battle, which eventually ended up with a 70-30 agreement in Federline’s favour. The divorce was finalised on the 30th of July, 2007. For Spears, it was the final moment of freedom before her conservatorship the following year, which remained in place until the September of 2021 after the ‘Free Britney’ movement led to it being stopped.
Sam Asghari – 14 Months
In 2016, Sam Asghari appeared in the video for Britney Spears’ new single Slumber Party. He later recalled, “I was excited that I would get to meet one of the biggest artists of all time; I had butterflies”. The pair entered a relationship almost immediately, with Asghari having been born in Iran and the youngest of four children. He immigrated to the United States of America when he was 12, arriving with his father. He went on to play football for the University of Nebraska-Lincoln, as well as joining the police academy before becoming a male model after his sister took him along to a runway show when he was 21.
After meeting on set for the music video, the pair exchanged phone numbers before going out for sushi and starting dating. He became a personal trainer, with the two of them regularly working out together in their home gym. Speaking to Men’s Health magazine, Asghari said, “She motivates me more than anyone. It’s crazy how I can be humbled by a person like her. If I could be that humble when I’m that high in life, that would be the best thing. I grew up with three sisters, and my personality is just to be a supportive person for my family and she’s family. I’m always going to support her. She is another blessing that happened to me”.
On the 12th of September, 2021, Britney posted on Instagram that he had proposed. His manager released a statement that said, “The couple made their long-standing relationship official today and are deeply touched by the support, dedication and love expressed to them”. Just a couple of weeks later, it was confirmed that a judge had finally ended the conservatorship that had been in place for 13 years. Britney, it was said, was ‘very excited to embrace her full freedom’. That took a turn on the 11th of April when she wrote on her Instagram account that what the pair had thought was a ‘food baby’ was actually a human one.
Sadly, Britney lost the baby a few months later. On the 9th of June, 2022, however, the pair got married at Britney’s Thousand Oaks home in Los Angeles; the place where Jason Allen Alexander tried to break in. None of her immediate family were invited to the ceremony, whilst her sons chose not to attend. On the 16th of August, 2023, it was confirmed that the pair were getting a divorce after having been married for just 14 months. In truth, though, it was one of the longest and most stable relationships that Spears had had, given that they had been together for seven years by the time that they separated. Britney was 41 and Asghari 29 at the time.