Jason Alexander Once Claimed He Was Britney Spears’ Friend With Benefits While She Dated Justin Timberlake

Britney Spears’ first husband, Jason Alexander, has recently made the news for interfering in the Grammy-winner’s wedding. But if Alexander was to be believed, this might not have been the first time he was in the middle of Spears and a significant other. Spears’ childhood friend once claimed that he was a friend with benefits to the star even while she was with Justin Timberlake.

Jason Alexander once claimed that Britney Spears’ mom initially forced their divorce

Britney Spears smiling while wearing a gold dress.
Britney Spears | Kevork Djansezian/Getty Images

As some may know, Spears’ first husband, Jason Allen Alexander, recently claimed that Spears’ mother was behind their divorce. The pair were only married for 55 hours before their partnership was cut short. Although it was once stated that they split due to their own decision, Alexander’s lawyer, Mark Goldberg, claimed otherwise.

“It was the mother interfering in and inserting herself into her daughter’s life,” Goldberg once told Daily Mail. “She came to Las Vegas, threw Jason out, and got him a plane ticket home.”

Given that the two married so quickly in Las Vegas, Goldberg wondered if either Alexander or Spears were sober when they decided to marry. But Alexander insisted they were both of sound mind. The two long-time friends were just in love, which made their sudden divorce hurt Alexander even more.

“Jason was confused because he loved Britney and he didn’t want to hurt her, but he was very afraid of her mother and management,” he continued. “This wasn’t a stranger she’d just picked up. They had known each other for years. He thought if he played the game and did what they asked, she’d come around, and he and Britney would be together.”

Goldberg believed this one incident had long-term ramifications for Spears that lasted her entire life.

“I really believe this particular event had a detrimental impact on Britney Spears’ life — the way she’s been controlled and the toll that has taken,” Goldberg said.

Jason Alexander claimed he and Britney Spears were long-term friends with benefits even while she was with Justin Timberlake

Justin Timberlake and Britney Spears were in a highly publicized relationship that lasted from 1999-2002. For the N’Sync alum, he fell for the pop star as soon as they met.

“I was in love with her from the start,” Timberlake once opened up to GQ(via CBS). “I was infatuated with her from the moment I saw her.”

Although Timberlake harbored no ill will towards the pop star after the breakup, he admitted that their separation wasn’t easy to handle. During the interview, he offered up a few reasons why their relationship didn’t work, but was vague on the details.

“I felt like she had a couple of opportunities to just sort of stick up for me, and she didn’t. Which is fine,” he said.

However, the breakup served as inspiration for Timberlake’s smash hit “Cry Me a River.”

“But at the time, you know, I fought back, and that’s the way I fought back. I used my mind. I came up with a song,” he said.

Some of the themes included in the 2002 hit song were betrayal and infidelity. This once fueled speculation that Spears might have been unfaithful to Timberlake, leading to their breakup.

Spears’ first husband Alexander, however, once claimed he hung out with Spears on occasion while she was still dating Timberlake. But according to his 2012 interview with ABC News, Alexander alleged that he and Spears were friends with benefits for years. Even while the singer was with Timberlake.

“There was an instance when [Britney and I] were hanging out,” Alexander claimed. “He had called, and I was … kicking it with her, kind of like the guy ‘behind the scenes’ no one knew about.”

Jason Alexander claimed he had no idea he was going to marry Britney Spears in Las Vegas

Alexander shared that when he was asked to accompany the “Gimme More” singer on a trip to Las Vegas, he thought nothing of it.

“It wasn’t really a booty call,” he said. “It was just, you know, a friend asking a friend to come on a trip.”

She flew her childhood friend over to Las Vegas in a private jet. According to Alexander’s account, the night escalated quickly when Spears unexpectedly asked him to marry her.

“She just came out and asked me,” he said. “She was like, ‘Well, let’s get married.’ And I was like, ‘Sure. You know, let’s do this.””

As his lawyer Goldberg claimed, Alexander insisted they weren’t under the influence of any strong substance. At the time, the two wed because it was what they both truly wanted.

“I went with my feelings,” Alexander claimed. “I was in love with her. … I feel like she felt the same way.”

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