Britney Spears' Dating History: From Justin Timberlake to Jason Alexander to Sam Asghari

Britney Spears has made a career out of singing about the ups and downs of being in love -- and she's got plenty of experience to back up her work!

The singer's gone through several boyfriends over the course of her career, and she's actually racked up a list of three (ex-) husbands in her time!

We're going to check out who the performer's been with over the years and see who she's been hanging out with lately.

Spears' been with plenty of dudes in the industry ... one of her earliest relationships was with Justin Timberlake, whom she met while they were costarring on "The Mickey Mouse Club" during their teenage years.

The pair went began dating in 1999, and they were spotted in each other's company during various public events and awards shows over the next few years.

However, the singers broke up in 2002, and Timberlake went on to release "Cry Me A River," which many of his fans speculated was about his relationship with Spears.

The "SexyBack" singer later issued a public apology to his ex-girlfriend in 2021 on his Instagram account, writing he had "failed" her.

Spears subsequently claimed she'd undergone an abortion in her 2023 memoir "The Woman In Me," and wrote that the experience was "agonizing," according to People.

In addition to the claim about her past pregnancy, she also alleged she had cheated on the singer with dancer Wade Robson ... although the experience was limited to a make-out session at a bar.

Following her split from Timberlake, Spears was linked to several individuals, including actor Colin Farrell, attending a film premiere with him in early 2003.

The singer's fling with the actor didn't last -- and she shocked the public when she married her childhood friend Jason Alexander on a trip to Las Vegas in January of 2004.

The thing is, the pair's union wasn't intended to be serious, and they wound up annulling their marriage after just 55 hours.

Spears later wrote that her parents traveled to Las Vegas after learning about their daughter's actions, and she claimed they "made way too big a deal out of innocent fun," according to People.

Spears then began a relationship with Kevin Federline -- who's previously performed as one of her backup dancers and later began a short-lived career as a rapper -- after the two met at a nightclub in 2004.

The pair embarked on a whirlwind romance, and they made things official in a ceremony in Studio City, Los Angeles, that same September.

Oh, and just in case you didn't think that was fast, we've got another one for you -- they started a family just a year after that with the birth of their first son Sean.

Spears and Federline welcomed a second son named Jayden the following September, and he arrived just four days before his big brother's first birthday.

But the performers' relationship came to a screeching halt in November 2006, and they finalized their divorce agreement the following July.

Spears didn't remain single for long after her divorce, as she moved on with several individuals, including paparazzo Adnan Ghalib ... although their relationship ended in 2008.

The singer started dating agent Jason Trawick in 2009, and the two wound up engaged after two years.

Although Spears and Trawick went split up in 2013, her representative issued a statement to ABC News in which the singer claimed she would "remain great friends" with her former fiancé.

The performer later started a relationship with David Lucado -- although they split up after she reportedly found a video of him dancing and kissing another woman during a night out in 2014.

Spears then dated producer Charlie Ebersol -- son of SNL co-creator Dick Ebersol -- but their relationship didn't last, and they broke up in June 2015.

Spears' next long-term relationship was with Sam Asghari, who played the lead in the music video for her 2016 track "Slumber Party" ... and the pair went Instagram official with their relationship in January 2017.

The two remained together for another four years before we shared a few snaps of the actor going ring shopping in Beverly Hills -- and you guessed it, he popped the question in September 2021.

Although the two had to navigate a miscarriage the following May, they worked through their grief and tied the knot in a star-studded ceremony in June 2022 -- oh yeah, and Alexander tried to crash the wedding ... but that didn't go so well for him.

The couple remained together for almost a year before rumors about trouble in the pair's marriage began to surface, and they officially split up that August.

Spears and Asghari worked out the terms of their breakup in the following months, and their divorce was finalized in May 2024.

The singer eventually moved on with Paul Soliz, who previously performed maintenance work at her home, first linked in 2023.

Spears and Soliz's relationship was seriously tumultuous, and a blowup at the Chateau Marmont in West Hollywood in May 2024 resulted in paramedics called to the scene.

Sources told us the singer and her former flame had an altercation in Las Vegas during the last week of December 2023, and when the dust settled, the singer apparently had to shell out a five-figure sum to cover the damages to their hotel room.

Spears and Soliz appeared to reconcile in early 2025, and the performer was spotted while hanging out with his kids that February.