Britney Spears' Complete Dating History: From High School Sweethearts to Walking Down the Aisle

"It was me being silly, being rebellious, and not really taking the responsibility of what I was doing."

Britney Spears has been in the spotlight for the majority of her life — and her relationships have been making headlines for just as long. Since her days as an aspiring pop star, Britney has had her ups and downs in the romance department, from dating some of the biggest stars in the world to an hours-long marriage in Las Vegas.

But now it appears that Britney has finally found her match in husband Sam Asghari. After sticking by Britney’s side through her conservatorship battle, the couple finally got the chance to walk down the aisle in a stunning ceremony with their closest family and friends. And with Britney finally free, the possibilities are endless for the newlyweds.

Take a look back on all of Britney’s past relationships…

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Reg Jones

When Britney was still a teen, she dated her classmate Reg Jones for two years. As she became increasingly more famous and her career took her around the world, she unfortunately had less time to focus on the couple’s relationship and ultimately broke up with Reg in a handwritten letter.

“When we broke up it was very tough. It ripped me apart. My head told me it was the right thing for both of us, but my heart told me a different story. We sat down on the porch at her mum and dad’s house and talked it through. There were hugs and kisses and we agreed to stay friends. We are still good friends and I’d get back with Britney tomorrow if I could, but it is very unlikely we ever will,” Reg said in an interview a few years after their split.

Justin Timberlake

In one of Britney’s most high profile relationships, she dated her former “Mickey Mouse Club” co-star Justin Timberlake from 1998 to 2002. The duo quickly became an A-list couple, regularly making red carpet appearances together. Things didn’t end on a good note for the two and following their split, Britney faced much criticism in the press for ending the relationship. Not only did Justin share intimate details about the couple’s sex life in interviews but he also cast a lookalike in his “Cry Me A River” music video, implying that Britney had cheated on him.

Many years later, Justin finally issued an apology for how he treated Britney, saying he was “deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right.” He added that he both cares for and respects Britney and knows he “failed.”

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Wade Robson

Following Britney’s breakup with Justin in 2002, she began dating dance choreographer Wade Robson — who was reportedly the cause of Britney and Justin’s split. Britney and Wade went on to date for about a year before going their separate ways.

Fred Durst

In 2003, Britney was linked to Limp Bizkit frontman Fred Durst while they were reportedly working on music together. While Fred maintains that the duo did have a fling, Britney says the whole thing was one-sided and she wasn’t interested in him.

“I think him for me, but not me for him. He’s said some pretty amazing things about me. But, um, I think he leaped in too deep, too quick,” Britney told the British version of Glamour magazine.

Colin Farrell

Later that year, Britney connected with Colin Farrell and after appearing on the red carpet together for his movie “The Recruit,” they were spotted making out on a hotel balcony. Nothing else appeared to develop between the duo.

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Columbus Short

That summer, Britney was spotted spending time with her backup dancer Columbus Short. Before the duo even got together, there were rumors in the press that they were dating. Many years later, Columbus clarified that he had only hooked up with Britney once and actually had been in a different relationship at the time.

“We ended up being intimate that one time. I never slept with her again after that, though. This was a dangerous sexual alliance for every reason under sun, and I think that the worst part of it was that I was making the rumors an actual reality,” Columbus wrote in his 2020 autobiography, “Short Stories.”

Jason Alexander

In 2014, Britney reconnected with her childhood friend Jason Alexander and after a night of partying in Las Vegas, the couple ended up tying the knot. The union didn’t last long as their marriage was annulled after just 55 hours.

“It was me being silly, being rebellious, and not really taking the responsibility of what I was doing, you know? And after partying, you know, you really don’t think about what you’re doing. So it was one of those things that were really silly,” Britney told E! News.

While the duo appeared to go their separate ways for many years, Jason recently resurfaced when he crashed Britney’s wedding to Sam Asghari. Jason, who was not invited to the event, broke into Britney’s home and live-streamed his attempts to get inside the wedding. He was charged with a stalking felony and misdemeanor counts of trespassing and refusing to leave private property, vandalism, and battery. Britney has since been granted a restraining order against him.

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Kevin Federline

Later that year, Britney began dating her backup dancer Kevin Federline. They had only been dating for two months when Britney suggested they get married. Four months later, they walked down the aisle, despite criticism of their relationship. Britney and Kevin went on to welcome their sons Sean Preston and Jayden but called it quits in November 2006.

“I think I married for all the wrong reasons. Instead of following my heart and, like, doing something that made me really happy. I just did it because…for just, like, the idea of everything,” Britney said in an MTV documentary.

J.R. Rotem

Not long after calling it quits with Kevin in 2006, Britney began dating music producer J.R. Rotem. The pair were only together for about two weeks, during which J.R. said they had sex “tractor style.” He added that they ultimately split because they “decided for both our careers that it would not be cool to have a romantic relationship.”

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Isaac Cohen

In early 2007, Britney was linked to model Isaac Cohen after they were seen boating off the coast of Los Angeles. They were spotted together on several other occasions but by February, they had called it quits. Isaac’s agent said the duo was both “busy with their careers” and were just “having fun together.”

Howie Day

In February 2007, Britney entered rehab where she met singer Howie Day. The duo was spotted playing tennis together during their very short time at Promises rehab center. The pair continued to spend time together post-rehab but ultimately went their separate ways.

Criss Angel

Later that year, Britney was briefly linked to magician Criss Angel after being spotted together on several occasions. The duo says their relationship was strictly professional though and Criss was just helping Britney with her MTV Video Music Awards performance. Unfortunately, their collaboration didn’t pan out.

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Adnan Ghalib

In December 2007, Britney began dating paparazzo Adnan Ghalib after encountering him numerous times while he was working as a photographer. Despite concern from Britney’s family, the pair continued to date at the height of her tabloid frenzy. During that time, she was placed under a psychiatric hold twice which ultimately led to her conservatorship being put in place.

Things appeared to fizzle out between the couple during the summer of 2008, but Adnan stayed in the headlines, claiming he had made a sex tape with Britney. He even reportedly continued to tip off the paparazzi off about Britney’s whereabouts. Things finally ended in January 2009 when Britney’s father Jamie filed a restraining order against him.

Jason Trawick

In 2009, Britney began dating her agent Jason Trawick. Despite the fact that Jason was involved in the professional side of Britney’s life, their relationship proved to be stable for her as she recovered from a tumultuous time. The pair got engaged in 2011 but never tied the knot, eventually splitting in 2013. In a statement, Britney simply said they had decided to call off their engagement but she would “always adore him” and they would “remain great friends.”

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David Lucado

Shortly after her split from Jason, Britney began dating lawyer David Lucado. They were together for about a year but Britney reportedly ended the relationship after she discovered that David had cheated on her.

Charlie Ebersol

In October 2014, Britney began dating producer Charlie Ebersol, whose father is “Saturday Night Live” co-creator Dick Ebersol. The couple spent about eight months together, which Britney documented on social media, but called it quits in June 2015.

Sam Asghari

Britney met her now-husband Sam Asghari in late 2016 on the set of her “Slumber Party” music video. The pair hit it off and exchanged numbers — although Britney didn’t follow up for a few months. Once they connected, they were inseparable and Sam stayed by Britney’s side as she faced the hardships that came along with her conservatorship.

The couple got engaged in September 2021 and in April of the following year, they announced they were expecting their first child. Unfortunately, the couple experienced a miscarriage but tried to remain positive as they moved forward with their relationship. On June 9th, 2022, the couple officially tied the knot.

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