How Many Times Has Britney Spears Been Engaged?

Britney Spears is no stranger to love and marriage. Currently dating actor and personal trainer Sam Asghari, many people don’t know that the 39-year-old entertainer has previously been engaged two times. Since Spears has been married three times and she has dated quite a bit over the years, the timeline can get a little confusing.

Back in 2004, Spears got engaged to then-backup dancer Kevin Federline. A surprise wedding and two sons later, the two split in 2006. Five years later, Spears got engaged again, this time to her former agent Jason Trawick. The two never made it down the aisle, splitting in 2013.

Many people think that Spears was also engaged to her childhood friend Jason Alexander. While the two did end up getting married, they were never actually engaged. They tied the knot in Las Vegas on New Year’s in 2004, according to ABC News. Celebrating the new year together, the pair partied the night away and then decided to get hitched. They headed to the little white wedding chapel where they exchanged vows.

“She just came out and asked me. She was like, ‘Well, let’s get married.’ And I was like, ‘Sure. You know, let’s do this,’” Alexander told ABC News in 2012. Fifty-five hours later, however, the marriage was annulled.

Later that same year, Spears met her first official fiance.

Here’s what you need to know:

Spears & Kevin Federline Got Engaged in 2004 After She Proposed

Getty ImagesSinger Britney Spears (R) and husband Kevin Federline arrive at the SONY BMG Grammy Party held at The Hollywood Roosevelt Hotel on February 8, 2006 in Hollywood, California.

Spears had some intense chemistry with Federline from the moment they met. When she headed out on her Onyx Hotel Tour, she decided to invite him along. The two chronicled their time together by way of home videos which later became the backbone for their short-lived reality show called Britney & Kevin: Chaotic.

A couple of weeks into the tour, Spears hurt her knee and she needed to have surgery. Forced to cancel her tour, she and Federline only got closer as they spent more and more quality time together. A few weeks into her recovery, Spears decided to ask Federline to marry her. Believe it or not, he said no — but then he proposed and she said yes.

Federline gave Spears a 5-carat bauble with a double band, both encrusted in diamonds, according to PopSugar.

From there, everything happened fairly quickly. The lovebirds invited their closest family and friends to an “engagement party” that turned out to be a surprise wedding. According to People Magazine, the couple decided to plan things this way due to the massive paparazzi attention they were getting — and they pulled it off.

“I just thought it would be too much if we had done it when we were supposed to. 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,” a 22-year-old Spears told the outlet in a post-wedding interview.

The couple had two boys over the next three years and ended up splitting in 2006. Spears filed for divorce on November 7 of that year. The divorce was finalized in 2007, according to Reuters.

Spears Got Engaged to Her Former Agent Jason Trawick in 2011

Getty ImagesJason Trawick (L) and Britney Spears arrive at the 2011 MTV Video Music Awards (VMAs) August 28, 2011 at the Nokia Theatre in downtown Los Angeles, California.

Spears had a few flings between Federline and Jason Trawick, but ultimately found love with her former agent. The two started dating in 2009, and two years later, Trawick got down on one knee. According to People Magazine, Trawick asked Spears to marry him on the night before his 40th birthday. The couple had been in Las Vegas when Trawick presented Spears with a ring designed by Neil Lane.

Spears and Trawick never made it to the altar. The two split in 2013, apparently wanting “different things.”

“There was no third party involved. Things haven’t been ideal in their relationship for some time. There was a lot to work on before they could move forward and get married,” a source told People Magazine at the time.

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