Flings, marriages and engagements! Britney Spears’ dating history

Written By: Pragati Awasthi | Updated: Sep 15, 2021, 07:50 PM IST

Pop legend Britney Spears has been in the spotlight for more than 20 years and apart from her conservatorship battle, her love life has also gained a lot of attention. As Spears announced her engagement to long time boyfriend Sam Asghari, take a look at her past relationship and flings.

File image of Justin Timberlake and Britney Spears

Britney Spears and Justin Timberlake are undoubtedly two of the most talked-about stars of their generation and their love life remains one of the hottest topics till date.

They dated from early 1999 until 2002. At the time, she was at the height of her career, while he was at the peak of his boy band days in NSYNC. The couple decided to pull the plug on their picture-perfect Hollywood relationship in 2002 after four years of dating and  things ended quite abruptly.


Wade Robson

After her split from Timberlake in 2002, Britney dated dance choreographer Wade Robson for about a year. However, there have been many rumours that she began hooking up with Wade before ending things with Justin. 


Fred Durst

After ending things with Wade Robson, Spears move on and made links with Fred Durst. Although Spears has denied that the two had a relationship.

"It just became a fiasco of madness," Durst told MTV of their split. "[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."



Jared Leto

In 2003, Britney and Jared Leto somehow crossed each other paths and were rumoured to be together during that year. She was dating Leto because his ex (Cameron Diaz) was dating Justin Timberlake (Spear’s ex), many reports says. 


Colin Farrell 

Britney and Irish actor Colin Farrell sparked major romance rumours when they attended the premiere of 'The Recruit' together in 2003. Later on, they were also spotted making out on his hotel room balcony! But Farrell denied that the two were in a relationship.


Columbus Short

Moving on, Britney hooked up with one of her backup dancers, Columbus Short. Their fling was short as soon separated because Columbus was a married man with 8 months, pregnant wife.


Jason Alexander

In 2004, Britney shocked everyone when she married her childhood pal, Jason Alexander, but her first marriage was short-lived. After marrying at the Little White Wedding Chapel in Las Vegas after a long night of partying, the couple annulled their union after 55 hours.


When she married Kevin Federline

In 2004, Britney Spears started dating Kevin Federline a background dancer and after few days of dating, they got married. Their whirlwind relationship confused everyone. Later she referred to her relationship as the biggest mistake ever but thanked him for their babies. 


JR Rotem

After ending things with Kevin Federline, Spears didn't stay single for long and briefly dated music producer JR Rotem in 2007. 


Adnan Galib

Britney Spears surprised everyone when she stepped out with paparazzo Adnan Ghalib. She briefly dated a photographer, despite all the fact that she was being hounded by paparazzi for months back then.

Although the relationship was short-lived, Adnan re-entered Britney’s life in 2012 when he testified in Sam Lutfi’s case against the singer.


Jason Trawick

After so many flings, Britney's most stable relationships and strong commitment come with former manager Jason Trawick. The pair’s relationship was confirmed in 2010 and they even got engaged in December 2011. Unfortunately, they never made it down the aisle. 

Jason even became a co-conservator for Britney and obtained legal control of the singer.


David Lucado

After ending her engagement with Jason, Britney began dating a lawyer, David Lucado, in 2013. The relationship lasted just over a year.


Charlie Ebersol

Adding more names to her dating list, Spears got together with Charlie Ebersol — a producer and the son of 'Saturday Night Live' co-creator Dick Ebersol — in October 2014.  

They even made public appearances on red carpets together. However, the relationship ended in 2015.


Sam Asghari

Two days after Sam Asghari posted a photo of a giant ring on Instagram and subsequently deleted it, his then girlfriend Britney Spears revealed that the couple had gotten engaged. 

The two shared the news on Instagram. "I can't f---ng believe it [?]!!!!!!" she captioned a video of herself showing off a giant ring on her ring finger. 

Sam is a fitness trainer and met Spears in 2016 on the sets of her music video 'Slumber Party'.