Britney Spears’s most recent marriage was to Sam Asghari and lasted about a year. But this isn’t her first rodeo – it’s her third, in fact! Her first marriage was in 2004 to childhood buddy Jason Alexander. The couple unexpectedly got hitched after a week of wild partying in Vegas. Their marriage lasted a record 55 hours before Spears got it annulled. Rumor has it that she went out dancing to celebrate after. She made news again later that year when she became engaged to Kevin Federline.
The two met on the dance floor of a Hollywood bar. Not one for conventions, Spears later proposed to Federline on her private jet. The pair then shocked their closest friends and family at their Studio City home with a surprise wedding celebration. The guests were completely blindsided. The couple divorced three years later.
Madonna believes that getting married "both times" had never been a good idea. Madonna married Sean Penn in 1985. Both stars were still young in Hollywood, head over heels in love. She even dedicated her third album, “True Blue,” to him. Their relationship lasted four years before the singer filed for divorce in 1989.
It took over a decade for Madonna to say "I do" again, this time to English filmmaker Guy Ritchie. Madonna filed for divorce in 2008 after an eight-year marriage. She once said that if she hadn't been an artist, she would have wanted to be a teacher. Such is her love for kids.
Kim Kardashian might be dating again but she’s not settling down again anytime soon. Kardashian's love life has dominated headlines since the early 2000s. She’s been married thrice: the first to music producer Damon Thomas, the second to former NBA player Kris Humphries (the infamous 72-day marriage), and the third to rapper Kanye West, from whom she divorced in 2021. They have four children together.
She’s blissfully single as of September 2022, stating that clearly, she’s doing something wrong in the relationship department. Her next tryst? The star imagines she might look for love with someone whose life is away from the spotlight.
The media has been obsessed with Angelina Jolie's love life over the years. After her divorce from Brad Pitt in 2016, Jolie shared in an interview that she felt “stronger” after, especially for her kids. Jolie has been married twice before. She met her first husband, Jonny Lee Miller while filming "Hackers." They were together from 1996 until 1999. Her next big relationship was with Billy Bob Thornton.
Soon, they began making headlines for outlandish displays of passion, including putting vials of each other's blood around their necks. They were married from 2000 until 2003. Jolie met her third husband, Brad Pitt on the set of “Mr. & Mrs. Smith” in 2005. Their love story and marriage immediately became a media sensation. They divorced in 2016.
Drew Barrymore may have loved and lost several times over. But she still considers herself a "hopeless romantic." She’s been married three times and engaged twice. Barrymore's first marriage, to Jeremy Thomas, lasted from 1994 to 1995. She then married actor Tom Green in 2001. Their marriage ended in under a year.
Barrymore was married to Will Kopelman from 2012 until 2016, and despite their divorce, they are still devoted to co-parenting their two girls, Olive and Frankie. But good news. She recently revealed she is on a dating app, reportedly with the most adorable profile photo. Barrymore says it took her some time to get to this stage after her divorce from Will Kopelman.