When Was Britney Spears Engaged to Jason Trawick, and Why Did They Break Up?

Britney Spears has had her share of relationships over the years. While many of her romances have been under the media’s watchful eye, one seemingly went under the radar. Back in the early 2010s, the pop superstar was in a relationship with her former agent Jason Trawick. The two were together for a few short years before ending their romance along with their engagement. Now that a recent podcast unearthed documents claiming the two secretly wed while they were together, we’re curious to know more about the former couple and their short-lived relationship.

Brtiney Spears posing with her ex-fiancé Jason Trawick on the red carpet at the 2011 MTV Video Music Awards
Britney Spears | Gregg DeGuire/FilmMagic

How long were Britney Spears and Jason Trawick together?

Following a heartbreaking divorce from her ex-husband Kevin Federline, Spears began dating Trawick in 2009.

According to Trawick, the singer was the one who made the first move, telling ELLE magazine in 2012, “It was kind of one of those things where she moved, like, turned around, so we were face-to-face.”

At first, the two kept a tight lip on their relationship, with media outlets confirming their romance.

“They are totally and definitely dating,” the source told People at the time. “Her dad loves him. He’s the best thing that happened to her.”

It wasn’t until January 2010 that the two finally went public with their love by attending the 52nd Annual Grammy Awards together.

Britney Spears and Jason Trawick attending the 52nd Annual Grammy Awards in 2010
Britney Spears and Jason Trawick | Lester Cohen/WireImage

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In December 2011, Trawick popped the question to the singer with a stunning Neil Lane-designed ring following months of engagement rumors. While it seemed like the Grammy winner had finally found her happily ever after, things between her and Trawick soon began going downhill, resulting in them calling it quits in 2013.

What happened between Britney and Jason Trawick?

In January 2013, media outlets reported that Spears and Trawick had mutually decided to end their engagement.

According to People, the pair wanted “different things” and felt they had to work on themselves before becoming husband and wife.

“There was no third party involved,” a source said. “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.”

The outlet also reported that Spears and Trawick weren’t on the same page when it came to the idea of maintaining lives outside of their relationship.

“Britney had a lot of issues with Jason doing his own thing – in business and seeing his friends,” a separate source explained. “In her perfect world he would have been home with her twenty-four/seven, so that was a point of contention; something they were always working on.”

The insider continued, “Britney wants to grow her family. Jason loves her boys but he is not in a place to have his own.”

At the time of their split, Trawick also stepped down as the “Toxic” singer’s co-conservator, which he petitioned to become in April 2012 while Spears worked to get back to being legally responsible for herself.

New court documents suggests Britney Spears married Jason Trawick in 2012

At the time of their split, media outlets made it seem that Spears and Trawick never made it down the aisle despite the singer’s desire to do so.

Now, many are questioning whether that’s still true after two podcast hosts discovered old court documents that seem to suggest otherwise.

Britney Spears posing with her ex-fiancé Jason Trawick at an event in 2011
Britney Spears and Jason Trawick | David Livingston/Getty Images

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On a recent episode of Toxic: The Britney Spears Story, co-hosts Tess Barker and Babs Gray examine the possibility that Spears and Trawick wed almost a decade ago.

According to Page Six, the hosts looked into an accounting report from the singer’s ongoing conservatorship case. They noticed that a $9,150 payment for “consultation [on] dissolution of marriage.” was made on Oct. 1, 2012, which was nearly one year into Spears and Trawick’s engagement.

The hosts reported that the payment was made to the “law offices of Alexandra Leichter,” a Beverly Hills-based family attorney. They also noted that the payment was listed under “conservatee’s legal fees.”

“My assumption would be that those were legal services that were rendered directly for [Spears’] benefit and nobody else’s,” estate specialist Austin Bertrand speculated in the episode. “‘Dissolution of marriage’ only means one thing, which is divorce.”

Of course, this caused the co-hosts to speculate whether Spears and Trawick actually were married. While it’s possible the couple wed and divorced in secret, nothing has been confirmed as of yet.