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A Timeline of Britney Spears and Ex Jason Alexander’s Ups and Downs

While Britney Spears has found The One in Sam Asghari, her June 2022 nuptials were technically her third trip down the aisle.

The pop star made waves in 2004 when she married Jason Alexander, a childhood friend, in Las Vegas. She sported jeans and a baseball cap for the impromptu nuptials. After just 55 hours, Spears’ team had the wedding annulled.

“It was me being silly, being rebellious, and not really taking the responsibility of what I was doing, you know?” the “Sometimes” singer later told E! News. “And after partying, you know, you really don’t think about what you’re doing. So it was one of those things that were really silly.”

Alexander, for his part, has had different memories of the events over the years.

“She just came out and asked me. She was like, ‘Well, let’s get married.’ And I was like, ‘Sure. You know, let’s do this,’” he claimed to ABC News in 2012. “I went with my feelings. I was in love with her. I feel like she felt the same way.”

The same year she had her quickie wedding with Alexander, Spears went on to marry Kevin Federline. After welcoming two sons — Season Preston and Jayden James — they split in 2006 and finalized their divorce in 2007.

Throughout her lengthy career, Spears’ personal life continued to make headlines. The Crossroads alum’s rocky relationship with her father and former conservator, Jamie Spears, came to a head in 2021 when she testified about the alleged mistreatment she endured amid her 13-year-old conservatorship. During the legal battle, Alexander, who attended several #FreeBritney protests, claimed that he was in contact with Britney.

“We stay in contact pretty regularly in the last few months. Last night via text message [was] probably the last time,” Alexander alleged in August 2020. “I’d love to be back in her life some way or another, but this conservatorship is holding that back from happening. We never were given a shot the first time around. If there’s feeling still there, maybe we see where they go but that’s not — you know that’s on her.”

A judge officially ended Britney’s conservatorship in November 2021. She accepted a proposal from Asghari several months prior and when they wed in June 2022, Alexander was arrested for three misdemeanors — trespassing and refusing to leave the property, battery and vandalism — for attempting to crash the wedding.

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