Britney Spears gained fame as “Princess of Pop” during the late 1990s and early 2000s, and has remained a prominent figure in tabloid news. Born on December 2, 1981, in Mississippi, the superstar became a sensation thanks to her unforgettable singles, “Baby One More Time” and “'Oops!... I Did It Again.” While Britney Spears has made a remarkable impact on musical culture and style, she has also been known for her notable romances over the years. From Justin Timberlake to Sam Asghari, here's a breakdown of her past relationships and marriages.

Before achieving worldwide fame as a solo artist, Justin Timberlake rose to prominence as one of the frontmen for the boy band *NSYNC, which was formed in 1995. At the age of 42, the American singer's fame extends beyond music for starring in several films including The Love Guru (2008) and Bad Teacher (2011).

Britney Spears and her first publicly known boyfriend, Justin Timberlake, confirmed their relationship in 1999, although they started dating while filming The Mickey Mouse Club. The two superstars became the most widely covered couple in entertainment, but their relationship came to an end in 2002.

Born on August 20, 1970, Fred Durst is a multi-talented artist known for his roles as a singer, songwriter, and director. He is widely recognised as the frontman and lyricist of the nu-metal band Limp Bizkit, formed in 1994.

Fred Durst and Britney Spears met when they collaborated on multiple songs for her 2003 album "In the Zone." While Durstopenly discussed their romance in his interviews in various interviews, Spears consistently denied these claims and affirmed their friendly relationship.

Jason Alexander, born on October 16, 1981, is Britney Spears' childhood friend, as they have known each other since they were kids living in Kentwood, Louisiana.

At the age of 22, Spearsmarried Jason Alexander, her first husband, on January 3, 2004, in Las Vegas, Nevada. However, their spontaneous marriage lasted just 55 hours before being officially annulled on Monday, January 5, of the same year.

Kevin Federline, also known as K-Fedis an American artist involved in dance, rap, acting, modelling, and DJing. Born on March 21, 1978, Federline was among Spears's background dancers.

Following a three-month romance, Federline and Spears announced their engagement in July 2004 and exchanged vows on September 18. The pair welcomed their sons, Sean Prestonborn in September 2005 and Jayden Jamesborn in September 2006. Nonetheless, their marriage took a turn for the worse, leading to a divorce three years later.

The American magician and illusionist Criss Angel is popular for starring in his live performance illusion show Criss Angel Believe and the show Criss Angel Mindfreak. He is now 55 years old and holds multiple world records achieved during his magic performances.

Britney Spears and Criss Angel were often seen together in 2007, but they always clarified that their relationship was strictly professional. According to Angel, he supported Spearson her MTV Video Music Awardsperformance and ended any personal relationship immediately after their collaboration.

In 2007, Isaac Cohen was 25 years old when he began dating the Princess of Pop. His modelling career has placed him in front of cameras and his popularity soared further as a result of his relationship with the A-list celeb.

Their dating rumours started circulating when the megastar and the model were seen enjoying a boating adventure in Marina Del Ray, California. However, their relationship was brief, and Cohen's agent officially announced their breakup.

Born in 1972 in Afghanistan, Adnan Ghalib spent his childhood in the UK. He later relocated to the United States and embarked on his career as a paparazzo for a California agency in 2007.

From 2007 to 2008, the ex-paparazzo found himself in the spotlight when he had a brief relationship with Spears. Their first public appearance as a couple was in December 2007, a surprise to their friends and family.

Jason Trawick is a Hollywood agent who worked for the “New York Daily News” but became an agent with one of the most powerful talent agencies on the planet, the “William Morris Agency”.

The singer of the hit “Sometimes” and her former manager, Jason Trawick began dating in 2009 and became engaged in December 2011. Nevertheless, they chose to end their engagement and announced their decision to split in 2012.

Charlie Ebersol is the son of former NBC Sports Chairman Dick Ebersol and actress Susan Saint James. He rose to prominence as a technology entrepreneur, television and film producer, and director.

The American entrepreneur, now 41, dated Britney Spears for eight months in 2014–2015. When they broke up in 2015, Britneydeleted all the pictures of him from her Instagram.

Sam Asghari, an Iranian-American model, actor, and fitness instructor, is renowned for creating “Asghari Fitness”, a platform specialising in personalised training programmes. Born on March 3, 1994, the fitness trainer found himself in the limelight through his relationship with the Grammy Award winner.

Spears started dating Sam Asghari in 2016, and their relationship progressed until the model confirmed their engagement in late 2021. Asgharimarried the singer in June 2022 in Los Angeles in an intimate ceremony. However, their story took a turn as the fitness instructor filed for divorce in August 2023.