Relive Britney Spears’ Past Relationships Ahead of Sam Asghari Wedding

On Jan. 3, 2004, she thought marrying her childhood pal Jason “Not of Seinfeld Fame” Alexander in Las Vegas seemed like a grand idea.

After some New Year’s partying that included sharing a kiss with one of her female dancers and flying Alexander into town from Louisiana via private jet, at around 5 a.m. Britney and Jason tied the knot. Though no one had ever heard of this dude before that night, in 2012 Alexander told ABC News that he and Brit had actually been FWB back in the day, even when she was dating Justin Timberlake.

So when the singer “was like, ‘Well, let’s get married’…I was like, ‘Sure. You know, let’s do this,'” he recalled. “I went with my feelings,” Alexander added. “I was in love with her…I feel like she felt the same way.”

They were married for 55 hours. The annulment stated that Britney “lacked understanding of her actions, to the extent that she was incapable of agreeing to the marriage.”

Britney told E! News in March 2004 that she was just “being silly, being rebellious, and not really taking the responsibility of what I was doing, you know? 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.”

She concluded, “I think I was running away from something. I didn’t quite know what…I’m still figuring out myself and learning every day. But I think I’m more in a good place. I like being alone, which is good I think. You know, I love reading books. I’m really a quiet kind of person right now. And so it’s cool to be back and feel like yourself again.”