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Britney Spears has found herself in headlines over her recent conservatorship drama – which may soon be coming to an end – but also for her relationship with aspiring actor Sam Asghari.
The two have been dating since about 2016 and announced their engagement just days ago, weeks after Spears implied in bombshell court testimony that she wants to have a baby with the fitness enthusiast.
With Spears, 39, set to say "I do," here’s a look at the star’s previous relationships:
Reg Jones (1995-97)
Britney Spears dated a boy named Reg Jones in her teenage years. (Jeff Kravitz/FilmMagic)
Us Weekly reports that before Spears was a massive star, she had a regular teenage romance with a boy named Reg Jones.
Not much is known about the relationship, but the outlet reports that she was only 14 when they started dating.
Justin Timberlake (1998-2002)
Britney Spears and Justin Timberlake dated from 1998-2002. (Getty Images)
Perhaps her most remembered relationship outside of her marriages, the pop star dated Justin Timberlake at the height of their popularity, making them one of Hollywood’s hottest couples.
After they split, Timberlake, now 40, famously wrote the song "Cry Me a River" about their split, seemingly alleging that Spears cheated on him.
He has since apologized for tarnishing her reputation in the public eye.
Wade Robson (early 2000s)
Britney Spears briefly dated Wade Robson in the early 2000s. (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)
Us Weekly reports that Spears and choreographer Wade Robson dated for about a year.
Colin Farrell (2003)
Colin Farrell and Britney Spears had a fling in 2003. (Photo by Kevin Winter/Getty Images)
The "Perfume" singer and "Ava" star Colin Farrell were spotted enjoying one another’s company in 2003 on his hotel room balcony and even attended the premiere of "The Recruit" together.
Farrell has since cleared up romance rumors, insisting that he was "just a 26-year-old guy who's single and having a good time."
BRITNEY SPEARS JOKES SAM ASGHARI IS AN 'A--HOLE' FOR 'OVERDUE' PROPOSAL BEFORE GUSHING OVER FIANCÉ
Columbus Short (2003)
Columbus Short and Britney Spears. (Photo by KMazur/WireImage for NFL)
Also in 2003, Spears was spotted sharing a kiss with dancer Columbus Short.
According to Us Weekly, he spilled the beans about his relationship to tabloids, which ended his marriage and his employment by Spears.
Jason Allen Alexander (2004)
Britney Spears was briefly married to childhood friend Jason Allen Alexander for 55 hours in 2004. (Getty Images)
Spears’ first marriage was to childhood friend Jason Allen Alexander. They wed in a Las Vegas chapel.
After just 55 hours together, the marriage was annulled. Rumors have swirled that Spears’ parents forced them to split despite their wishes to stay together, though the "Crossroads" star has stayed relatively mum on the subject.
SAM ASGHARI SAYS HE AND BRITNEY SPEARS WILL HAVE A PRENUP, MOCKS TROLLS FOR ASKING
Kevin Federline (2004-2007)
Britney Spears was married to Kevin Federline from 2004-2007. (Photo by Jason Merritt/FilmMagic)
Later in 2004, the pop star wed Kevin Federline at just 22 years old.
They raised two sons together – Jayden, 16, and Sean, 15 – before splitting in 2007.
J.R. Rotem (2007)
Britney Spears dated J.R. Rotem in 2007. (Photo by Michael Bezjian/WireImage)
In 2007, the singer rebounded from her divorce, dating music producer J.R. Rotem.
BRITNEY SPEARS ANNOUNCES ENGAGEMENT TO BOYFRIEND SAM ASGHARI FLASHING 'ONE OF A KIND RING'
Isaac Cohen (2007)
Spears also dated Isaac Cohen in 2007. (Photo by Jean Baptiste Lacroix/WireImage)
After Rotem, Spears dated model Isaac Cohen in a brief whirlwind romance.
Their busy schedules reportedly led to their amicable split.
Howie Day (2007)
Singer-songwriter Howie Day and Britney Spears were in a relationship briefly in 2007. (Photo by Mychal Watts/WireImage)
Spears entered rehab in 2007, which is reportedly where she met singer Howie Day.
However, after Spears’ mother Lynne learned of Day’s previous arrest, the mother reportedly intervened to end the relationship.
Adnan Ghalib (2007-2008)
Paparazzo Adnan Ghalib dated Britney Spears from 2007-2008. (Photo by Michael Bezjian/WireImage)
Spears and paparazzo Adnan Ghalib's public relationship didn’t last long but had an impact on the star’s life. Ghalib testified in Spears’ lawsuit against former manager Sam Lufti years later in 2012.
Jason Trawick (2009-2013)
Britney Spears had a years-long relationship from 2009-2013. (Photo by Michael Kovac/Getty Images for City of Hope)
Spears dated Jason Trawick from 2009-2013.
They became engaged in 2011 but never married, with rumors that their romance simply fizzled out. Other rumors suggested they secretly wed, but Trawick has denied that.
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David Lucado (2013-2014)
Attorney David Lucado and Britney Spears were involved from 2013-2014. (Photo by Charley Gallay/Getty Images for Neuro)
Not long after splitting from Trawick, Spears was seen out and about with lawyer David Lucado.
They dated for a little over a year, and it seemed Spears was ready for the split, tweeting, "Ahhhh the single life!" at the time, per Us.
Charlie Ebersol (2014-2015)
Britney Spears and Charlie Ebersol were together from 2014-2015. (Photo by Jon Kopaloff/FilmMagic)
Producer Charlie Ebersol and the singer dated for a few months between 2014 and 2015.
A source told Us Weekly at the time that he was in the relationship for "the wrong reasons."
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Sam Asghari (2016-present)
Britney Spears is engaged to actor Sam Asghari. (Photo by Kevin Winter/Getty Images)
Spears' current relationship is with 27-year-old actor and fitness enthusiast Sam Asghari.
They met in 2016 when he was featured in her "Slumber Party" music video. Though they’ve generally stayed mum about the relationship, they’ve gushed over one another from time to time, and Asghari has spoken out in support of his love amid her intense conservatorship battle.
They announced their engagement in September 2021, with Spears calling their engagement "overdue."
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