TIMELINE: Britney Spears’ boyfriends, break-ups through the years

MANILA, Philippines – Iranian-American model Sam Asghari has filed to legally separate from pop star Britney Spears after 14 months of marriage, multiple US outlets confirmed on Wednesday, August 16.

According to Entertainment Tonight, Asghari noted “irreconcilable differences” as the cause for their separation. The couple had been rumored to be going through marital issues, which included allegations of Spears cheating. Earlier in March, Ashgari’s rep had denied the rumors to People.

The two met during the singer’s music video shoot for “Slumber Party” back in 2016. After six years of dating and getting engaged in 2021, Spears and Ashgari tied the knot in an intimate yet star-studded Los Angeles wedding in July 2022.

The ex-couple’s marriage hasn’t always been smooth sailing, following Spears’ tumultuous conservatorship battle and her miscarriage in May 2022. 

Asghari was Spears’ third husband – one of her longest relationships yet – while she was his first wife.

Here’s a brief look back on the 41-year-old singer’s relationship timeline:

Reg Jones

Before her rise to fame, Spears dated Reg Jones during her teenage years. According to The Independent, the star’s high school sweetheart put her handwritten letters chronicling their two-year relationship up for auction.

Justin Timberlake

Arguably her most iconic ex-flame, The Mickey Mouse Club alums dated from 2000 to 2001. His song “Cry Me A River” and his previous remarks on their relationship resulted in backlash for the young Spears. He has since apologized to the star in 2021.

Jason Alexander

Alexander was Spears’ first husband. Spears got married to her childhood friend in a 2004 Las Vegas wedding, with their marriage clocking in at merely 55 hours. Alexander also attempted to crash her wedding with Asghari, landing him four criminal charges.

Kevin Federline

Shortly after her brief marriage with Jason Alexander, Spears then got engaged to dancer Kevin Federline within three months of knowing one another. The marriage blossomed into a family, welcoming two sons Sean Preston and Jayden James. They even had their own reality show. The couple later divorced in 2007.

Adnan Ghalib

The paparazzo dated Spears following her 2007 divorce. Ghalib even lent his testimony in support of the singer in her 2012 trial against former manager Sam Lufti, People reported.

Jason Trawick

Spears terminated her professional relationship with former manager Jason Trawick after deciding to pursue each other romantically in 2009 and later getting engaged in December 2011. Trawick also acted as co-conservator alongside her father, Jamie Spears. The couple called off their engagement in January 2013. 

David Lucado

Two months after the end of her engagement with ex-fiance Trawick, Spears began dating lawyer David Lucado. The relationship ended a little over a year later, amid rumors of Lucado’s cheating and the star taking to Twitter to declare, “Ahhhh the single life!”

Charlie Ebersol

Spears met the photographer and television producer through a mutual friend. The couple often shared snapshots of their day-to-day through Instagram posts. Their relationship lasted from October 2014 until June 2015.

Asghari would then be Spears’ most recent beau.

Spears is known for hits such as “Toxic,” “Oops!…I Did It Again,” and “Baby One More Time.” She recently collaborated with will.i.am for song “MIND YOUR BUSINESS” and is set to publish her memoir entitled The Woman in Me. – with reports from Mika Geronimo/Rappler.com

Mika Geronimo is a Rappler intern.