Inside Britney Spears' love life: From Justin Timberlake to Kevin Federline and Sam Asghari

A timeline of the singer's relationships over the years.

Britney Spears' tell-all memoir, The Woman in Me, has finally been released, with the singing sensation owning the narrative of her own story.

In it, she reveals how she felt about being held under a conservatorship by her family, the ups and downs of her career and life in the public eye and she talks about having an abortion when she was just 19.

Britney Spears on stage
Britney Spears has just released her memoir The Woman In Me. Photo: Getty Images

"Over the past 15 years or even at the start of my career, I sat back while people spoke about me and told my story for me," she told People magazine.

"After getting out of my conservatorship, I was finally free to tell my story without consequences from the people in charge of my life."

Part of her journey will be the partners that she had along the way and according to Page Six, her ex, Justin Timberlake, is concerned about what she has to say.

"He’s very curious what she’ll reveal from their relationship," one source explains. "It’s eating at him."

Here we take a look back at her boyfriends and partners over the years.

First boyfriend

Her high school boyfriend when she was 14 was 17-year-old footballer Reg Jones.

"She was my best friend as well as my girlfriend," he told British tabloid The Mirror in 2000.

"Britney is a fantastic girl. She loved to laugh, she loved to have a good time but she was also incredibly loyal and honest."

The Timberlake years

Justin and Britney met on the set of The Mickey Mouse Club in the early-90s and they started dating in 1998, eventually breaking up in 2002.

"I was in love with her from the start. I was infatuated with her from the moment I saw her," Justin said about first meeting Britney, according to People magazine.

Pictures of Justin Timberlake and Britney Spears
For four years, Justin Timberlake and Britney Spears were the music world's darling young couple. Photo: Getty Images

In a shock revelation from her upcoming memoir, Britney revealed that during the four years that they dated, she fell pregnant and subsequently had an abortion.

"It was a surprise for me it wasn't a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I'd anticipated," she wrote in the book.

"But Justin definitely wasn't happy about the pregnancy. He said we weren't ready to have a baby in our lives, that we were way too young."

Speaking about her abortion, Britney wrote: "Abortion is something I never could have imagined choosing for myself, but given the circumstances, that is what we did."

Jason Alexander

Britney admitted recently she had a brief fling with Australian choreographer Wade Robson after discovering Justin had cheated on her.

After her break-up with Justin, it's believed Britney had a dalliance with Limp Bizkit frontman Fred Durst before she tied the knot with her childhood pal Jason Alexander at the Little White Chapel in Vegas.

The January marriage lasted a mere 55 hours but it wasn't to be her last wedding in 2004.

Britney Spears childhood friend Jason Alexander and the Little White Chapel in Vegas
Britney married her childhood friend Jason Alexander at the Little White Chapel in Vegas in 2004 but the pair thought better of it two days later. Photo: Getty Images

Kevin Federline

Also in 2004, Britney met dancer Kevin Federline and theirs was a whirlwind romance. Just three months after the couple met, they wed at a party that their friends and family thought was going to be a celebration of their engagement.

Britney Spears and Kevin Federline during their relationship
Britney and Kevin had two children together - Sean Preston, now 18, and Jayden James, now 17. Photo: Getty Images

The couple had their two children, Sean Preston and Jayden James in quick succession in 2005 and 2006 but by the end of 2006, the marriage was over.

In the year that followed, Brit reportedly had a series of flings to mend her broken heart including with music producer J.R. Rotem, actor and model Isaac Cohen and singer Howie Day.

 Wade Robson, Limp Bizkit frontman Fred Durst, model Isaac Cohen, music producer J.R. Rotem and singer Howie Day.
After her splits from major loves Justin Timberlake and husband Kevin Federline, Brit had flings with Wade Robson, Limp Bizkit frontman Fred Durst, model Isaac Cohen, music producer J.R. Rotem and singer Howie Day. Photo: Getty Images and Facebook/howieday

Adnan Ghalib

After years of being hounded by photographers, many were surprised when Brit started dating paparazzo Adnan Ghalib in December 2007.

British paparazzo Adnan Ghalib with Britney Spears
British paparazzo Adnan Ghalib started dating Britney in December 2007. Photo: Getty Images

"I do not think Adnan is a good person; I think he only has bad intentions," Britney's cousin Alli Sims told US Weekly in February 2008 about the photographer who had been part of the pack that followed the singer everywhere she went.

"He has always given me a weird feeling and creeped me out. I wish he would just go away."

The relationship didn't last much longer than that summer.

Jason Trawick

Despite Britney's relationship with her former manager, Hollywood agent Jason Trawick, taking place while she was under conservatorship, many who know Britney think Jason was one of the most steadying and stable relationships Britney has had.

Britney and her former partner Jason Trawick
Britney and her former manager Jason Trawick were together for 4 years, getting engaged in 2011. Photo: Getty Images

The couple got engaged two years and a half after they started dating at the end of 2011 but they didn't make it down the aisle, splitting up in January 2013.

"Jason and I have decided to call off our engagement. I'll always adore him and we will remain great friends," Britney said in a statement sent by her representative to America's ABC News.

David Lucado

Britney described her attraction to lawyer David Lucado as 'Instant' when she told Ellen DeGeneres about the relationship during an interview.

Britney Spears with partner David Lucado at the People's Choice Awards and Elton John's Academy Awards party
Britney spent just over a year with lawyer David Lucado. Photo: Getty Images

"I just love that he's very passionate and he's funny and he's sexy and I don't know, I like him. I just love him," she revealed at the time. But the relationship only lasted a year.

Charlie Ebersol

After David, Britney started dating Charlie Ebersol, the son of Saturday Night Live co-creator, Dick Ebersol.

"There was something about him that made me feel really peaceful and at ease," she told People magazine, adding: "And he was really hot, too. Adorably hot."

Britney Spears with producer Charlie Ebersol at the 2015 Billboard Music Awards
Britney spent just under a year with producer Charlie Ebersol Photo: Getty Images

The couple were together for eight months with TMZ reporting that the split up wasn't messy but that Ebersol reportedly signed an NDA. at the beginning of their relationship.

Sam Asghari

Then in October 2016, Britney met her most recent husband, actor and model Sam Asghari when she was 35 and Sam 23.

Britney and her husband Sam Asghari at the Daytime Beauty Awards in 2019 and at the LA premiere of Once Upon a Time ... in Hollywood
Britney and her husband Sam Asghari started dating in 2016 and finally married in 2022 but it wasn't to be. Photo: Getty Images

The couple got engaged in September 2021 and Sam was there for Britney when her conservatorship ended in November of that same year.

The couple tied the knot in a small ceremony in June 2022 but in August this year, the couple filed for divorce citing 'irreconcilable differences'.

The reported that Sam explained the split in a since-deleted Instagram post saying: "After 6 years of love and commitment to each other my wife and I have decided to end our journey together.

"We will hold onto the love and respect we have for each other and I wish her the best always."

He added: "Asking for privacy seems rediculous [sic] so I will just ask for everyone including media to be kind and thoughtful."

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