A look back at Jason Alexander and Britney Spears’ romance

A look back at Jason Alexander and Britney Spears' romance 2
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Britney Spears’ first husband Jason Alexander was arrested after dramatically livestreaming himself crashing her wedding at her California mansion on Thursday afternoon. 

The singer, 40, was preparing to marry her long-term partner Sam Asghari, 28, in a lavish ceremony at her Thousand Oaks home but just hours before the event was due to start, Alexander broke onto the premises to crash the wedding. 

After her ex was detained by the Ventura Sheriff’s Department, Britney was seen returning to her home alongside Sam in her white Mercedes Benz and the couple later tied the knot in front of a star-studded crowd that included the likes of Paris Hilton and Drew Barrymore – yet not her estranged family or her two sons.

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MailOnline takes a look at the history of their relationship… 

Third time lucky: Britney, 40, was preparing to marry her long-term partner Sam Asghari, 28, in a lavish ceremony at her Thousand Oaks home (pictured in 2021)

Third time lucky: Britney, 40, was preparing to marry her long-term partner Sam Asghari, 28, in a lavish ceremony at her Thousand Oaks home (pictured in 2021)

Childhood pals Britney and Alexander tied the knot on a whim in the early morning hours on January 3, 2004 during a ceremony at the Little White Wedding Chapel in Las Vegas, Nevada. They were both 22 years old at the time.

Their marriage was annulled 55 hours later, which Alexander later claimed was forced by Britney’s mother, Lynne, and Britney’s management.

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Following the annulment, Britney said in an interview: ‘It was me being silly, being rebellious.’ 

Gatecrashing: Britney Spears' first husband Jason Alexander was arrested after dramatically livestreaming himself crashing her wedding at her California mansion on Thursday afternoon

Gatecrashing: Britney Spears’ first husband Jason Alexander was arrested after dramatically livestreaming himself crashing her wedding at her California mansion on Thursday afternoon

Former flame: Spears was married to Alexander for just 55 hours in January 2004 after a spur-of-the-moment ceremony in Vegas

Former flame: Spears was married to Alexander for just 55 hours in January 2004 after a spur-of-the-moment ceremony in Vegas

Throwback: Childhood pals Britney and Alexander tied the knot on a whim in the early morning hours on January 3, 2004 during a ceremony at the Little White Wedding Chapel in Las Vegas (pictured in 2002)

Speaking to ABC's 20/20 show in 2012, Alexander reflected on the events, saying 'I was in love with her. … I feel like she felt the same way' (pictured in 2005)

Throwback: Childhood pals Britney and Alexander tied the knot on a whim in the early morning hours on January 3, 2004 during a ceremony at the Little White Wedding Chapel in Las Vegas

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Speaking to DailyMail.com, retired divorce attorney Mark Goldberg last year revealed how a distraught Alexander turned to him after he was kicked out of Britney’s life following their now infamous marriage stint.

He was also of the view that the annulment was the first insight into the singer’s powerlessness over her own life, saying that it had a devastating impact ever since.

Goldberg also claimed that neither Britney nor Alexander wanted the annulment and recalled how Alexander reached out to him in a series of emotional phone calls, seeking advice after the singer’s mother threw him out of their Las Vegas hotel suite and his new bride’s life less than three days after their marriage.

Wedding blues: Asked what he had learned from the marriage, Alexander replied: 'Nice guys finish last. Look out for yourself'

Wedding blues: Asked what he had learned from the marriage, Alexander replied: ‘Nice guys finish last. Look out for yourself’

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Star couple: The star announced her engagement to backing dancer Kevin Federline in July 2004, just seven months after her brief marriage to Alexander (pictured in 2005)

Star couple: The star announced her engagement to backing dancer Kevin Federline in July 2004, just seven months after her brief marriage to Alexander (pictured in 2005)

He continued: ‘I really believe this particular event had a detrimental impact on Britney Spears’s life – the way she’s been controlled and the toll that has taken.

‘The whole situation stuck with me all through the years because I feel sorry for the kid.

‘He really hoped they’d get back together. Instead, she moved on with her life and career and got married again.’

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The star announced her engagement to backing dancer Kevin Federline in July 2004, just seven months after her brief marriage to Alexander.

Break-up: The couple had two sons, Sean, 15 and Jayden, 14, before Spears filed for divorce in 2006 in a split that was finalised the following year (pictured in 2005)

Break-up: The couple had two sons, Sean, 15 and Jayden, 14, before Spears filed for divorce in 2006 in a split that was finalised the following year (pictured in 2005)

The couple had two sons, Sean, 15 and Jayden, 14, before Spears filed for divorce in 2006 in a split that was finalised the following year.

Speaking to ABC’s 20/20 show in 2012, Alexander reflected on the events, saying ‘I was in love with her. … I feel like she felt the same way’.

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In the annulment papers for the marriage, it was claimed that Britney ‘lacked understanding of her actions, to the extent that she was incapable of agreeing to the marriage’.

But Alexander says of that claim, ‘Bull***t. That was probably the hardest part about it. I had obviously got my feelings involved.’

Asked what he had learned from the marriage, Alexander replied: ‘Nice guys finish last. Look out for yourself.

‘If you are going to really get involved into a relationship with a celebrity and you are just an average Joe, make sure you are thinking business!’

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As well as her rocky history with marriages, Britney has also had a string of high-profile relationships, starting with Justin Timberlake. 

The pair struck up a romance years after meeting on The Mickey Mouse Club in the 90s – they confirmed their romance in 1998 and split in 2002.

It was rumored Britney had cheated on Justin with dance choreographer Wade Robson.

In the same year her 2007 divorce was finalised, Britney also briefly dated music producer J.R. Rotem.

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Love: Spears and tied the knot after her 13-year conservatorship came to an end - she and Sam met in 2016 (pictured in March 2022) - it's the singer's third wedding

Love: Spears and tied the knot after her 13-year conservatorship came to an end – she and Sam met in 2016 (pictured in March 2022) – it’s the singer’s third wedding

Britney’s three marriages: from shock stint with childhood pal to crashed wedding  

Jason Alexander (2004)

Britney’s first (brief) marriage was to Jason Alexander, who had been her friend since childhood.

They eloped in Las Vegas at the Little White Wedding Chapel, but they famously got the union annulled after just 55 hours of married life.

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Kevin Federline (2004)

Just seven months after her annulment, Britney announced her engagement to backing dancer Kevin Federline. She had met him three months earlier.

The pair tied the knot at a secret ceremony in Studio City, California.

Britney soon became pregnant with their first child Sean, who was born in 2005.

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A year later the couple welcomed their second son Jayden. 

Britney and Kevin finalised their divorce in 2007, with sources claiming Kevin’s partying was ‘the last straw’ for Britney, according to People.

Sam Asghari (2022)

Britney married her longtime partner Sam Asghari- in a ceremony in Thousand Oaks, California – which was sensationally crashed by her ex Jason Alexander.

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Britney and Sam tied the knot after the singer’s 13-year conservatorship came to an end.

The singer met the 28-year-old fitness trainer and actor on the set of her music video for Slumber Party in 2016 and by January 2017, the couple were Instagram official.

They got engaged in September 2021 and earlier this year announced they were expecting their first child together; before Britney later sadly told fans she had suffered a miscarriage.

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