A 55-hour marriage and multiple engagements: A brief history of Britney Spears' relationships.


If anyone is winning at life during lockdown right now, it’s definitely Britney Spears.

The singer, who is currently celebrating the 20th anniversary of her iconic debut album ‘Oops!… I Did It Again’, has been sharing snippets of life in self isolation on Instagram over the last few months.

From dancing to Justin Timberlake’s ‘Filthy’ to sharing hilarious memes about social distancing, the 38-year-old has gained even more fans in isolation.

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Spears, who has two sons, Sean and Jayden, from her previous relationship, has also been sharing videos of her elaborate at-home workouts with her boyfriend-slash-personal trainer Sam Asghari, who is 28 years old.

Although little is known about the couple’s relationship, the pair, who share a 13 year age difference, have been dating since 2016.

The couple first met on the set of her music video for ‘Slumber Party’ in 2016.

“I was excited that I got to meet one of the biggest artists of all time,” Asghari recalled, speaking to Men’s Health. “I had butterflies.”

After cracking jokes with Spears on set, Asghari reportedly gave Spears his number and five months later, Spears finally contacted him.

“I was like, ‘He was really cute, this guy was really cute,’ so I called him,” Spears recalled in a radio interview.


“He’s just a really fun, funny person.”

Speaking to Entertainment Tonight in 2019, Asghari shared that marriage is “absolutely” on the cards for the couple.


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“This is something that every couple should do. That’s the point of a relationship – we are a family,” he said.

“Trust me, if we do ever get married, everybody’s going to know,” he added.

The 28-year-old also shared that his family adores Spears, adding: “We’ve been together for three years and my sisters love her, my family loves her. My mum lives in another country [but] when she was here, she met her.”

As the couple continue to share their lockdown workouts on Instagram, we decided to take a look back at Britney Spears’ relationship history.


Justin Timberlake

Amid their three-year relationship, Britney Spears and Justin Timberlake were the undisputed King and Queen of pop music.

In December 1992, Spears was cast in The Mickey Mouse Club at 12 years old alongside Christina Aguilera, Keri Russell, Ryan Gosling, and Justin Timberlake.

Despite meeting at such a young age, childhood friends Spears and Timberlake didn’t start dating until 1998. Spears was booked as the support act on an NSYNC tour that lasted 18 months, during which time the pair started dating.

In the years they dated, both Spears and Timberlake achieved major career success as Spears became the best-selling teenage artist of all time, and Timberlake had further hits with NSYNC.

Britney Spears Justin Timberlake double denim
Britney Spears and Justin Timberlake at the 2001 American Music Awards. Image: Getty.

In 2001, the couple famously wore matching double denim outfits to the American Music Awards.

The outfit – her sweetheart-neckline denim dress and low-slung belt, and his full denim suit and matching denim fedora hat – has been recreated thousands of times at Halloween and fancy dress parties.

But in 2002, the couple's iconic relationship abruptly came to an end.

Amid their break-up, Timberlake released the song 'Cry Me a River' as the second single from his debut album, which sparked rumours that Spears had been unfaithful.

Although it was rumoured that Spears had had an affair with choreographer Wade Robson, NSYNC member Lance Bass has since claimed it never happened.

britney spears 2018
Justin Timberlake and Britney Spears. Image: Getty.

Following their split, Spears was briefly romantically linked to musician Fred Durst, actor Colin Farrell, backup dancer Columbus Short, and Jared Leto.

Jason Alexander

In January 2004, Spears made a spur of the moment decision to marry her childhood friend, Jason Alexander.

The couple were married at The Little White Wedding Chapel in Las Vegas.

Just 55 hours later, the marriage was annulled, following a petition to court which stated that Spears "lacked understanding of her actions".

In an interview with ABC News in 2012, Alexander shared that the childhood friends were often "friends with benefits".

"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,'" he recalled.

"I went with my feelings," he added.


"I was in love with her. I felt like she felt the same way."

britney spears boyfriend
Jason Alexander. Image: Getty.

Kevin Federline

In July 2004, Spears became engaged to Kevin Federline – just three months after meeting the American dancer.

Their relationship was chronicled in the reality show Britney & Kevin: Chaotic.

Three months after they were engaged, the pair held an intimate wedding ceremony in Studio City, California.

Shortly after tying the knot, the couple began to express their desire to become parents. "Next year at 23, I am so there," Spears told People at the time.


In 2005, the couple's first child, Sean Preston was born. They welcomed their second son, Jayden James, in 2006.

But just eight weeks after Jayden was born, Spears, then 24 years old, filed for divorce, citing irreconcilable differences.

In the months that followed, Spears famously shaved her head and eventually lost custody of her children when she was hospitalised in a psychiatric ward.

britney spears boyfriend
Kevin Federline and Britney Spears. Image: Getty.

"I was going through so much artificial stuff with my kids and Kevin at the time. He’d just left me and I was devastated," she told MTV in an interview for the 2008 documentary For the Record.

"People thought that it was me going crazy and stuff like that, but people shave their heads all the time. I was going through a lot, but it was just kind of like me going through a little bit of rebellion, or feeling free, or shedding stuff that had happened, you know?"

A judge awarded her father control of Britney's personal and financial affairs. The conservatorship is still in place today.

Despite their divorce, Federline and Spears have gained a relatively positive co-parenting relationship.

"It's been a long, long journey, but I think where both of us are now, we both have somebody else we're happy with. Everything just works," Federline said in 2015.

Federline is now married to Victoria Prince. The couple have two daughters together – Jordan Kaye and Peyton Marie.


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Jason Trawick

In 2009, after being romantically linked to a number of people including illusionist Criss Angel, Spears began dating her now-former manager, Jason Trawick.

The pair ended up getting engaged in late 2011, but by January 2013, the pair mutually ended their engagement.

"There was no third party involved," a source told People at the time.

"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."

britney spears boyfriend
Jason Trawick and Britney Spears in 2012. Image: Getty.

After her relationship with Trawick, Spears briefly dated David Lucado, until he was caught publicly cheating on her.

Between 2014 and 2015, Spears dated film producer Charlie Ebersol for eight months, before deleting all evidence of their relationship from her Instagram feed.

In 2016, she began her relationship with her current boyfriend, Sam Asghari.

Feature Image: Getty/Instagram.

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