HomeEntertainmentBritney Spears' Dating History: Justin Timberlake, Kevin Federline and More

Britney Spears’ Dating History: Justin Timberlake, Kevin Federline and More

The dating history of the pop star Britney Spears is all things iconic! Last year, she tied the knot with her longtime boyfriend Sam Asghari. But before that, the Oops! I Did It Again singer was romantically linked to many top celebrities such as Justin Timberlake, Colin Farrell, and more.

The ‘Princess of Pop’ had a high-profile romance with the Can’t Stop the Feeling singer  Justin Timberlake. The pair met each other on the sets of The Mickey Mouse Club in the ’90s. They confirmed their romance in the year 1999. They called it quits in 2002. Back in the day, their split was quite a topic of discussion among the fans.

Soon after, Britney moved on in her life. Before Sam, she walked down the aisle a total of 2 times and got engaged three times. Keep scrolling further to catch more insights about the romantic life of Britney Spears.

Reg Jones (1995-1997)

Before Britney Spears became a big name in the music industry, she was a regular teenager growing up in rural Louisiana. According to a report by Us Weekly, at the age of 14, she had a boyfriend named Reg Jones.

It has been reported by the media outlet, that Reg Jones was the guy Spears lost her virginity to. Britney’s lawyer Eric Ervin confessed to Us that Britney’s virgin image was a “PR blitz.”

Justin Timberlake (1998-2002)

A love story straight out of Mickey Mouse Club! Back in the day, Justin and Britney were the ultimate pop couple. The two of them were in a relationship from early 1999 to 2002. At that time, Timberlake was at the height of his boy band days in NSYNC, on the other hand, Spears was also at peak of her early career.

Justin and Spears pulled the plug on their relationship in the year 2002 after 4 years of dating. The pair didn’t end their romance on a happy note. Later on, down the lane, Timberlake went on write a song Cry Me A River reportedly about Britney’s infidelity.

However, over the years, the former pair drift apart, they complimented each other on social media in 2020. The next year, Justin offered a public apology to Spears after her documentary Framing Britney Spears put some light on Timberlake’s behavior after their split.

At that time, the Rock Your Body singer took to his Instagram page and wrote, “I’ve seen the messages, tags, comments, and concerns and I want to respond. I am 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 for what’s right.”

Justin went on to say, “I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism. I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed.”

Then, a source told Us Weekly, that Britney doesn’t hold a grudge against Timberlake over anything he has said or done. The insider said, “She feels that they were young and in love and both did stupid things when they were together. She was heartbroken when they separated, but it’s not something she dwells on now. She’s happy and happy for him.”

Wade Robson (2001-2002)

After her split from Justin, Britney went on to date dance choreographer Wade Robson. The duo was in a relationship for about a year from the year 2001 to 2002. There have been rumors that Spears started dating Wade before ending things with Justin.

As of this moment, Britney has never made any official comment on these rumors. For those of you who are unaware, let us share with you, Wade is one of the men who has accused Michael Jackson of sexual abuse, and his claims were the subject of the 2019 documentary named Leaving Neverland.

Fred Durst (2003)

In 2003, the Toxic singer was rumored to be dating Limp Bizkit frontman, Fred Dunst. However, Britney denied that the two of them were an item back in the day. In an interview with MTV, she talked about Fred and stated that she was never in a relationship with him.

At that time, Spears told the media outlet, “It just became a fiasco of madness. [But] I always stay true to my heart and true to everything I did and my intentions, and I am in no way a liar.”

Colin Farrell (2003)

Britney and Colin Farrell sparked dating rumors when they attended the premiere of The Recruit together in 2003. Later on, they were seen packing on the PDA on the balcony of his hotel room.

Although, Colin denied that the two were in a relationship. At that time, he insisted that he was “just a 26-year-old guy who’s single and having a good time.”

Columbus Short (2003)

After being linked to Colin, Britney hooked up with one of her backup dancers, Columbus Short. The following year, Short talked about his hookup with the Gimme More songstress during an interview with Star magazine.

In the same interview, Columbus admitted that it led to the end of his marriage. At that point, his wife was pregnant with their first child. Soon after, his employment with Spears also ended.

Jason Alexander (2004)

In 2004, Britney shocked her fans all over the world when she tied the knot with her childhood friend Jason Alexander. The pair said their vows at the Little White Wedding Chapel in Las Vegas. Their marriage wasn’t built to last for eternity.

Jason and Spears’ marriage is one of the most short-lived celebrity marriages of all time. They annulled their union after just 55 hours of getting married. The singer filed a petition with the court, which stated that she “lacked understanding of her actions” at the time of the nuptials.

On June 9, 2022, Alexander was arrested by the cops after he tried to crash Britney’s wedding to Sam. In a video on his Instagram live, he recorded himself breaking into Spears’ wedding in Thousand Oaks, California as police arrested him.

Kevin Federline (2004-2007)

During the same year, Britney met backup dancer Kevin Federline. The two of them got engaged just 3 months after meeting. They exchanged their vows in September 2004 (although the nuptials were not legalized until a few weeks later).

Around the same time, Kevin’s ex Shar Jackson was pregnant with his second child. Federline and Britney welcomed two kids together. Their first son, Sean Preston joined them earthside in September 2005. Their second son, Jayden James was born in 2006. Britney and Kevin split in the year 2006. Their divorce got finalized in July 2007.

J.R. Rotem (2007)

After her divorce from Kevin, Britney didn’t waste much time getting back on the dating scene. She began dating music producer J.R. Rotem in the year 2007. However, there were widespread rumors that she started dating Rotem while she was still with Kevin.

Isaac Cohen (2007)

As per Us Weekly, Britney’s next fling was with Isaac Cohen. The pair was first clicked by the paps while powerboating off Marina Del Ray, California. The fans noticed some similarities between Isaac and her ex-husband Kevin.

The two of them spend a lot of time together during their relationship and mutually called things off due to their busy schedules.

Adnan Ghalib (2007-2008)

At the end of the year 2007, Britney was snapped with a man from the paps: Adnan Ghalib. She briefly dated photographer Adnan Ghalib. However, their romance was short-lived. Adnan made a comeback in Spears’ life in October 2012 when he testified in a heated trial between Spears’ former manager Sam Lufti and her family.

Jason Trawick (2009-2013)

Then, Britney went on to date her former manager Jason Trawick. The pair dated for 5 years from 2009 to 2013. Their romance was confirmed in the year 2009. According to a report by Hollywood Life, they got engaged in 2011.

Trawick even became a co-conservator for Britney and obtained legal control of the singer. Sadly, their romance fizzled out and they pulled the plug on their romance at the start of 2013. Then, Jason was removed as her conservator.

At that time, a source told Us Weekly, “Everyone knew Jason was leaving her but Britney. She’s in la-la land.” Britney’s relationship with Trawick was one of her most stable relationships.

David Lucado (2013-2014)

Post her split from Jason, the Baby One More Time singer started dating a lawyer, David Lucado, in the year 2013. The pair’s romance lasted for just one year, and by 2014 they went their separate ways.

In August 2014, Britney’s representative confirmed the news of her split from David to Us Weekly. At that time, the singer tweeted, “Ahhhh the single life!”

Charlie Ebersol (2014-2015)

After all these flings, Britney started a romance with producer Charlie Ebersol who is the son of Saturday Night Live co-creator Dick Ebersol in the year 2014. But in June 2015, Us confirmed the news of their breakup.

At that time, the media outlet reported that Charlie was in it “for the wrong reasons.” Soon after their split, the pop star removed all the pictures of the pair from her Instagram feed.

Sam Asghari (2016-present)

Britney met her current husband Sam on the sets of the music video of her song Slumber Party in the year 2016. Britney and Sam made their romance Instagram official in January 2017. In a radio interview, Spears said, “I was like, ‘Helate-nighty cute, this guy was really cute,’ so I called him. He’s just a really fun, funny person.”

Since then the two of them have been inseparable. They have been spotted together at late-night parties, cozy date night dinners, and more. During a 2018 interview with Men’s Health, Sam raved about his ladylove Britney.

The fitness model said, “I was excited that I [would] get to meet one of the biggest artists of all time, I had butterflies. She motivates me more than anyone. I’m always going to support her. She is another blessing that happened to me.”

Sam and Spears got engaged in September 2021. On September 12, 2021, the Can You Keep a Secret? actor proposed to the love of his life. They shared the piece of good news with their fans all over the world on Instagram.

At that time, Asghari’s manager Brandon Cohen issued an additional statement to People magazine. Then, he stated he is “proud to celebrate and confirm the engagement.” Cohen went on to say, “The couple made their long-standing relationship official today and are deeply touched by the support, dedication and love expressed to them.”

Then, Brandon also went on to reveal that Britney’s new ring was designed by N.Y.C. jeweler Roman Malayev, founder of Forever Diamonds in New York. Cohen continued, “He couldn’t be happier to be involved and make this one-of-a-kind ring.”

Britney and Sam got married in a beautiful wedding on June 9, 2022. They exchanged their vows in front of a small group of friends such as Drew Barrymore, Paris Hilton, and Selena Gomez.
For the big day, the Born to Make You Happy singer donned a gown by the famed fashion house Versace. She walked down the aisle to Elvis Presley’s smashing hit single Can’t Help Falling In Love.
After the pair’s wedding, Sam’s manager Brandon told People magazine, “I am very ecstatic this day has come, and they are married. I know he wanted this for so long. He is so caring and supportive every step of the way. I am so grateful to have Sam in my life and can’t wait for the future they will build together.”
Britney’s sons Sean Preston and Jayden James whom she shares with her ex-husband Kevin Federline did not mark their attendance at her wedding to Sam Asghari. At that time, Kevin’s lawyer told Entertainment Tonight, that they wish their mom all the happiness.
Then, Federline’s attorney issued a statement that read, “Although the boys will not be in attendance, Kevin and the boys are happy for Britney and wish her and Sam all the best going forward.”

We are happy that Britney Spears has found her soulmate in Sam Asghari. The two of them make for a gorgeous couple. Don’t forget to stay tuned with us for the latest updates from the world of showbiz.

Meenal Mehta
Hi, I am Meenal. I'm a travel enthusiast, a movie buff and a cricket fan all wrapped in one. I love to capture moments through my words. Writing is my happy space, it has been a great way of putting all my thoughts out and feel liberated.


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