Looking Back at Britney Spears' Two Weddings and Marriages

While Britney Spears is currently in a relationship with Sam Asghari, the pop star has been married twice before. The year was 2004 and Spears walked down the aisle twice—once to wed her childhood friend Jason Alexander and the other to marry Kevin Federline, the latter of which she was married to for three years.

Ahead, all the details on the princess of pop's two former husbands, weddings, relationships, and more.

Jason Alexander, January 3, 2004

It was a whirlwind marriage for Spears and her childhood friend Jason Alexander (no, not the Seinfeld star!). After a fun-filled New Year's Eve week in Sin City, where she partied at Rain and Ghostbar, Britney shocked the world by tying the knot. Like Ross and Rachel before them, Spears and Alexander did the whole middle of the night, drunken, quickie Vegas marriage in a green stretch limo thing.

"It was just so crazy, man," Alexander told Access Hollywood. "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.'"

Dressed in a baseball hat and ripped jeans, the singer paid $70 to say her "I dos" in Vegas's A Little White Wedding Chapel at 5 a.m. on Sunday, January 3rd, 2004. "They weren't dressed in wedding attire, but it was very romantic and there was a feeling of love between them," chapel owner Charolette Richards told Rolling Stone. "They appeared to be extremely happy. They were laughing, but crying, too, during the ceremony. I thought it was a marriage that would last forever."

55 hours later, however, the pop princess had the union annulled. Spears reportedly went out dancing after.

Kevin Federline, September 19, 2004

Oops, she did it again! After meeting on the dance floor—where else!—at Hollywood club Joseph's, the Spears and Kevin Federline announced their engagement in July of 2004. The singer famously balked with tradition and popped the question to Federline on her private plane. "Then all of a sudden I said, 'What if you want to get married?' And I kind of went from there to asking him if he would marry me. I asked him... He said no because he thought it wasn't the right way to do it," the singer told People. A week later Federline slipped a 5-carat diamond engagement ring on her finger.

The pair set off planning a wedding for October 16, 2004, even sending out 100 invitations to the event. After too much paparazzi attention and stress, the couple surprised the world with a top-secret wedding! "It became this huge thing and I was like, 'What are we waiting for? We know this is the real thing, why not just do it now?' That's why I wanted to sneak and do it our little way," she told People.

The couple surprised 30 of their closest friends and family with a wedding at their Studio City home—guests thought they were attending an engagement party. Wearing a $26,000 strapless Monique Lhuillier wedding dress, she accessorized with lace half-gloves and a cathedral-length veil. For the casual backyard reception, the bride changed into another Lhuillier dress, this time a very mini lace number, complete with the traditional garter, which Federline removed with his teeth. After the reception, featuring a menu of chicken fingers, crab cakes, ribs, and mashed potatoes, the newlyweds and their wedding party (wearing matching sweatsuits!) hit up hotspot XES for a late night of dancing.

Two kids, one reality show, and three years later the couple would call it quits.

In 2016, Spears told James Corden she would never get married again. "I think [I won't] ever do the whole men thing anymore, or get married. I'm just done with men—I may French kiss someone, but I won't ever get married." That doesn't mean she shouldn't make an appearance on every wedding playlist, however!