Britney Spears and Jason Alexander: 55 Hours
It all began — and ended — on New Year’s in 2004. Brit-Brit invited her childhood friend to Las Vegas and flew him in on a private jet. "She just came out and asked me," Alexander recalls. "She was like, 'Well, let's get married.' And I was like, 'Sure. You know, let's do this.'" A whopping 55 hours after “I do,” that marriage was annulled — and poor Jason admits he was heartbroken.