Britney Spears' ex-husbands and boyfriends: Who has Britney dated?

BRITNEY Spears has just announced her engagement to her boyfriend of five years Sam Asghari.

But the star hasn’t always been that "Lucky" when it comes to love. From countless flings and rumored affairs, to even getting married for 55 hours, this star seems to have experienced it all.

Who are Britney Spears' ex husbands?

Jason Alexander

Britney shocked everyone in 2004 when she decided to marry her childhood friend, Jason Alexander.

The pair married at Little White Wedding Chapel in Las Vegas after a long night of partying and then got divorced 55 hours later.

Kevin Federline

If it wasn’t already apparent that Britney had a thing for her backup dancers, she married Kevin in 2004.

The pair ended up having two children together but divorced in 2007.

Later Britney referred to that relationship as the biggest mistake ever but thanked Kevin for their babies, Sean and Jayden. 

Who are Britney Spears' ex boyfriends and fiances?  

Reg Jones

Reg Jones is Britney’s first boyfriend back in high school from her home town in Kentwood, Louisiana.

Captain of the school’s football team, 17-year-old Reg had his eye on 14-year-old Britney.

The pair dated for two years before deciding to call it quits.

Reg has since come out and said how he remembers how shy she was when he asked her out.

He said: "She just didn't believe me when I asked her.

"I was the one everyone looked up to. I was the famous one then."

Look how the tables have turned.

Justin Timberlake

Justin Timberlake and Britney were the prince and princess of pop at the time

The pair met when they were just 11 years old as they shared the screen in the Mickey Mouse Club in 1992.

They stayed friends until 1999 where the couple went public about their relationship.

They made fashion history at the 2001 American Music Awards when they both arrived wearing double denim on the red carpet.

This moment is still referenced today as one of the most iconic moments of red carpet fashion and in the history of love.

The couple ended their relationship after two years.

Neither star has commented on the real reason as to why they finished but it was rumored that Britney cheated on Justin with her choreographer, Wade Robson.

Was Justin's Cry Me A River song about Britney?

Wade Robson

While never confirmed, it was rumored that Britney dated Wade for just under a year with the possibility of there being a cross over from her previous relationship with Justin.

Britney and Wade grew close after he co-directed her 1999 and 2000 world, but neither party has commented on any of the rumors about their relationship.

The pair weren't the most liked couple but rumoured to have been together for just under a year.

Robson is often associated with Britney’s "rebellion" period.

Fred Durst

Fred and Britney had a short fling back in 2003 after a collaboration for her new album, but it was short lived as it only lasted for around four months.

Fred has publicly confirmed that he had a relationship with Britney whilst herself and friends have all denied this to be true.

He also accused Britney of “playing him out” and that it was more than just a platonic relationship.

Jared Leto

Britney met Jared at a posh LA restaurant called Dolce.

In 2003 it was rumoured that Britney and Jared were dating, which if true would have been ironic as his ex Cameron Diaz became public with her new relationship with Justin Timberlake (Spear’s ex).

Colin Farrell 

Irish actor Colin Farrell sparked dating rumors when they attended the premiere of The Recruit together back in 2003.

The pair were then later photographed on the balcony from his hotel room making out.

Farrell has denied that the two were ever in a relationship.

Columbus Short

Moving on, Britney started hooking up with one of her backup dancers, Columbus Short.

At the time, Columbus said Britney's parents were firmly against their relationship. 

Their fling was short-lived as Columbus was married with an eight month pregnant wife.

Reflecting back at their relationship Columbus told Inside Hollywood that he believes Britney was just using him for her own gain and to make her parents mad.

JR Rotem

Once Britney’s marriage to K-Fed was over she didn’t stay single for long, and was rumoured to have a fling with music producer JR Rotem in 2007. 

JR spoke with Complex magazine and confirmed that they did have a relationship but he described it as “tricky” as he didn't want to be “tied down”.

He also mentioned how dating Britney helped grow his popularity as she had “gotten him the furthest”.

Jason Trawick

After having countless rumored flings the star settled for another stable relationship with Jason Trawick.

The couple decided to go public with their relationship at the 2012 Grammy Awards, as they showed up together hand-in-hand.

The pair confirmed their relationship in 2010 and even got engaged in December 2011, although that’s the furthest their relationship got and ended as they wanted “different things” out of life.

Many fans believed that the couple were married for some time before the split as numerous sources pointed out that Britney had accidentally referred to Jason as her “husband”.

David Lucado

After her engagement with Jason, Britney began dating lawyer David Lucado for just over a year.

Their romance didn't blossom into anything serious as in late 2014, Britney announced that she was single by tweeting, “Ahhhhh the single life!”

It was rumored that David was recorded dancing and kissing another woman, to which Britney's father purchased the video to avoid public embarrassment.

Eventually David addressed the situation and confirmed that the man in the video was not him.

Charlie Ebersol

Britney then began dating Charlie Ebersol, a producer and son of Saturday Night Live co-creator Dick Ebersol in 2014.

The couple were very public with their relationship making multiple public appearances together but it didn’t last long as it all ended in 2015.

Many sources weren't surprised that their relationship didn't work out as they described it as “written in the clouds”.

Both parties have said that it just fizzled out due to busy work and life schedules.

Sam Asghari

Sam is a fitness trainer who met Britney on her music video set Slumber Parties.

The couple have been together for five years and got engaged in September 2021.

Britney has shared the video of her engagement which she was posted to Instagram.

“You like it?” Asghari asks in the video, to which Britney Spears excitedly replies: “Yes!”

Britney captioned the post: “I can’t f**king believe it,” along with numerous engagement ring emojis.

Asghari uploaded a separate post of the couple kissing as Britney holds up her ring finger to the camera.

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