Details About Britney Spears' Short-Lived Marriage With Jason Alexander

Singer Britney Spears broke onto the music scene as the opening act for groups like 'NSYNC. However, after she released her first single "... Baby One More Time” in 1998, she shot to fame and was soon headlining her own sold-out shows. An interest in Spears' personal life also skyrocketed, especially because she was dating fellow singer Justin Timberlake of 'NSYNC. Following their heartbreaking split in 2002, however, Spears was all about having fun. She was rumored to have dated Fred Durst, Colin Farrell, and Jared Leto, according to Us Weekly. Also during that period of her life, Spears reconnected with an old friend named Jason Alexander, and, during a wild night out in Las Vegas in 2004, the two decided to get married. 

Pictures of Spears, then 23 years old, and Alexander at a wedding chapel in Sin City were all over the internet within hours. The "Oops! I Did It Again" singer wore a pair of ripped denim jeans with a garter on her thigh. She also had on a long-sleeve, black crop top, and a white baseball hat. Her groom was also dressed casually in jeans and a T-shirt and a black coat. And while the world watched with their mouths hanging open, Spears and Alexander ended up having one of the shortest marriages in history. According to the Daily Mail, the union was annulled 55 hours later. In a 2012 interview, Alexander opened up about his wedding with the world's biggest pop star.

In an interview with ABC News, Jason Alexander recalled Britney Spears calling him up and inviting him to go to Las Vegas to hang out with her. While they were there partying, he says, she suggested they get married. "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 explained. "I went with my feelings. I was in love with her. ... I feel like she felt the same way."

However, Alexander said the singer's family and management team freaked out because the two didn't have a prenuptial agreement. And so, the marriage ended almost as fast as it happened, and Alexander says it was hard because he really cared for Spears.

The two would eventually drift apart and Spears moved on romantically, linking up with dancer Kevin Federline, whom she'd later go on to marry. However, Spears was never too far from Alexander's mind. In fact, when a judge ordered her conservatorship in 2008, Alexander kept a close eye on what was happening. In 2020, he actually attended a "#FreeBritney" protest in Los Angeles. "This is an unfortunate situation that's been in her life for a long time. It's affected me and her, and that makes me part of it. I've been quiet for 10 years," he told Us Weekly at the time. 

Although Jason Alexander hasn't been seen with Britney Spears since they ended their marriage, he says that they've been in touch. While chatting with Us Weekly in 2020, Alexander said that they'd been talking. "We stay in contact pretty regularly in the last few months. Last night via text message [was] probably the last time," he explained. After Spears' conservatorship ended in November 2021, she felt as though she could officially move on with her life — and she decided that she wanted to get married for a third time. Spears and beau Sam Asghari tied the knot in Los Angeles in June 2022. And the wedding had an unexpected guest — Alexander. 

Alexander showed up at his ex's home and decided to document the whole thing on Instagram Live, according to E! News. "I'm here to crash the wedding because nobody is here except Sam. Where the f*** is the family?" he said, calling it a "bulls*** wedding." Alexander ended up being taken down by security and was arrested when police arrived due to an outstanding warrant from a different county. He was later charged with aggravated trespassing and battery and was sentenced to 64 days behind bars, Vanity Fair reported. He was also given strict orders to stay at least 100 yards away from Spears.