Britney Spears’ first husband, Jason Alexander, has had a pretty tragic love life. In 2004, Alexander, who grew up with the beloved pop star, cemented himself into Spears’ dating history when they married at a Las Vegas wedding chapel after a particularly eventful night. “It was just crazy, man,” Alexander shared with Access Hollywood (via BBC). “We were just looking at each other and said, ‘Let’s do something wild, crazy. Let’s go get married, just for the hell of it.'” Unfortunately, he only got to be married to Spears for a couple of days, as their marriage was annulled 55 hours later at the urging of her team.

At the time, Spears’ lawyer claimed that Alexander was supportive of the annulment. “Jason agreed to this completely,” he shared with BBC. “They’ve made a wise decision. I know they care about each other. They are friends.” Alexander was also quoted as calling their marriage a “mistake” that had to be corrected. However, Spears’ short-lived husband had changed his tune by 2012 when speaking with ABC News. During a candid interview, Alexander, who claimed he was in love with Spears, expressed disappointment over the frantic way her team and family had the marriage dissolved. “They didn’t want to hear anything … and [Spears] came back, and it ended,” Alexander revealed. 

Alexander also expressed regret over being a “nice guy” and not pushing back against the annulment. “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!” he said. Unfortunately, that wouldn’t be the only thing he would come to regret.

Britney Spears’ wedding to Jason Alexander barely counts as a marriage in the grand scheme of things, but that didn’t do anything to impact Alexander’s feelings for her. In 2022, Alexander made major headlines when he tried to gain entry to Spears’ wedding to her third husband, actor-model Sam Asghari. Spears and Asghari opted to have the star-studded wedding at Spears’ home in Thousand Oaks, California, and Alexander decided to crash it, live-streaming his time on the property. While he claimed he was there to talk to Spears, the experience ended with Alexander being arrested, charged, and found guilty of several crimes, including trespassing and battery, according to People. He served roughly two months in jail. Spears also sought a restraining order.

Unfortunately, all of Alexander’s trouble was for nothing. In 2023, upon the release of Spears’ memoir, “The Woman In Me,” the singer downplayed their short-lived marriage. “He and I got s***faced,” she wrote (via Time). “I don’t even remember that night at all, but from what I’ve pieced together, he and I lounged around the hotel room and stayed up late watching movies — ‘Mona Lisa Smile’ and ‘The Texas Chainsaw Massacre’ — then had the brilliant idea of going to A Little White Chapel at three thirty in the morning.” She continued, “People have asked me if I loved him. To be clear: he and I were not in love. I was just honestly very drunk — and probably, in a more general sense at that time in my life, very bored.”