It’s fitting that ‘Oops!… I Did It Again’, the iconic lyric of pop sensation Britney Spears’ hit song, also aptly sums up her whirlwind dating history that includes as many as 11 boyfriends and rumoured romances.
Following her recent split from husband and American model Sam Asghari, Britney appears to be enjoying her singlehood. However, this isn’t her only breakup that’s captured the public’s attention.
Britney Spears has a dating history as colourful as her music career. From teenage heartthrobs to Hollywood’s leading men, Britney’s romantic life has been a rollercoaster ride of high-profile romances that have dominated pop culture. In fact, while giving a sneak peek of her upcoming memoir, The Woman in Me, Britney Spears reflected on pivotal moments in her life, including her relationships.
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Intriguingly, a noteworthy revelation from her memoir was that Spears had to terminate a pregnancy with singer and actor Justin Timberlake as the latter wasn’t ready to embrace parenthood at such a young age.
Throughout the pop princess’ time in the spotlight, particularly in the ’90s and 2000s, Spears has been involved in highly publicised romances. Unsurprisingly, fans are eager to hear Spears’ personal accounts of these relationships in her memoir.
But for those who can’t wait for her book, which is set to release on October 24, and are intrigued by her love life, we present a comprehensive look at Britney Spears’ boyfriends. So, without further ado let’s deconstruct her dating history, shall we?
A look at Britney Spears’ boyfriends and dating history
From Justin Timberlake to her now ex-husband Sam Asghari, here’s a look at Britney Spears’ dating history.
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Reg Jones (1996-1998): The high school sweetheart
Reg Jones, o primeiro namorado de Britney Spears leiloa itens da cantora como demos inéditas, fotos, cartas e até sutiã e calcinha. pic.twitter.com/nhHkxUF6Nb
— Britney Spears Brasil (@BSpears_BR) April 29, 2018
High school romances are always special and Britney’s teenage years were not immune to puppy love. Donald Reg Jones was Spears’ high school sweetheart and first taste of romance in the limelight. The two dated for two years and Britney broke up with him through a mushy handwritten letter.
Reg Jones admitted in 2021 that Britney was “the love of my life.” Rumours also suggest that the pop star lost her virginity to Jones. Ah, to be young and in love!
Justin Timberlake (1998 to 2002): The pop power couple
Britney Spears reveals in her memoir that Justin Timberlake cheated on her with another celebrity during their releationship, TMZ reports. pic.twitter.com/oPeU0KO3XJ
— Pop Base (@PopBase) October 18, 2023
Next up on the list of Britney Spears’ boyfriends is singer and actor Justin Timberlake, her first highly public relationship. The pop icons, who first stole hearts as co-stars on The Mickey Mouse Club, navigated the complexities of fame and young love during the late 1990s and early 2000s.
In her upcoming memoir, Britney candidly shares intimate details of her life, including her high-profile relationship with Justin Timberlake. One of the memoir’s most poignant revelations revolves around an unexpected turn in their relationship – Spears’ unplanned pregnancy. The pop sensation discloses the emotional turmoil she experienced despite her desire to embrace parenthood as Timberlake was not ready to become a father. The couple, deeply in love yet grappling with the challenges of youth and fame, made the difficult decision to undergo an abortion. Spears expresses her internal conflict, revealing that if the choice had been solely hers, she might have chosen to have the child.
As per Justin, however, the two split because Spears had cheated on him. The former NSYNC member also released a song – ‘Cry Me a River’ – about it, with the music video featuring a Britney lookalike.
Wade Robson (2002): The dancing flame
Shortly after her breakup with Timberlake, Britney was linked to dancer and choreographer Wade Robson. He even appeared in the music video for ‘(You Drive Me) Crazy’, though neither confirmed the relationship.
Colin Farrell (2003): The Irish charmer
Britney Spears & Colin Farrell ❤️❤️❤️ pic.twitter.com/BIIukYYClG
— Aaron (@ABeardedHero) March 7, 2022
Next on the list of Britney Spears’ boyfriends is Irish actor Colin Farrell whom she was rumoured to be dating back in the early 2000s. In 2003, they turned heads when they were seen holding hands at a movie premiere. The tabloids went wild, but Colin kept it casual, explaining they were just mates who’d recently met and were “having a laugh.”
Jason Alexander (2004): Short-lived Vegas vows
NEW booking photo for Britney Spears ex Jason Alexander.
He was booked into Napa County jail at 5:30 Tuesday for felony grand theft after he took plea deal and was sentenced to time served for crashing her wedding. pic.twitter.com/06VesqHYtb
— Britney Access (@BritsAccess) August 17, 2022
After a string of dating rumours, Britney Spears left fans shocked by spontaneously tying the knot with childhood friend Jason Alexander at a Las Vegas chapel in 2004. To everyone’s astonishment, just a mere 55 hours later, they annulled the marriage.
The plot thickened in 2022 when Alexander, craving his share of the spotlight, attempted to crash Britney’s wedding to Asghari. He even dubbed Britney as his “first and only wife.” Things took an even more bizarre turn when he was arrested for trespassing and vandalism.
Kevin Federline (2004 to 2007): Dancing into romance
Britney Spears and Kevin Federline’s Relationship Timeline https://t.co/S5z6MEaPeE
— People (@people) October 18, 2023
Next on the list is Kevin Federline, the dancing sensation who caught Britney’s eye at a club in 2004. After only three months of dating, the lovebirds threw a surprise wedding in September of the same year. The surprises didn’t end there – just before celebrating their one-year anniversary, they welcomed their first child, Sean Preston. In 2006, their second son, Jayden James, joined the family.
While it looked like Britney had finally found her happily ever after, she filed for divorce in November 2006, citing ‘irreconcilable differences.’
Their initial divorce settlement granted the two joint legal and physical custody of their two children, seemingly putting them on amicable terms. However, in 2018, Federline requested a USD 20,000 per month increase in child support payments from Britney.
After months of legal wrangling, Federline doubled down, demanding a staggering USD 40,000 per month. Finally, in September 2018, they reached a settlement, with Britney increasing her child support payments to Federline to USD 35,000 per month.
Adnan Ghalib (2007-2008): The British paparazzo
britney spears & adnan ghalib pic.twitter.com/mU6S5mxgZE
— photostreaming (@photostreaming) June 2, 2023
For Britney Spears, the paparazzi have practically been her shadow. So it wasn’t too surprising when, in 2007, a British paparazzo named Adnan Ghalib boldly stepped into the spotlight. It all began with the iconic head-shaving incident, which she pulled off in front of roughly 70 paparazzi. It was at this time that Adnan entered the orbit of Britney’s romantic life.
Their love story had a brief yet intense run, lasting just about a year before fizzling out in 2008. Fast forward to 2021, and we got an exclusive peek into their romance through the Netflix documentary, Britney vs Spears. Ghalib reminisced about their time together, describing it as “a very simple, very easy relationship.” But, oh boy, the world painted him as the villain, thanks to her devoted fans and the media frenzy.
The finale of their rollercoaster romance took place in 2008 when, in an interview, Ghalib publicly revealed that Britney had been hoping and longing to be pregnant with his child. The drama escalated, and in 2009, Britney’s father, Jamie Spears, had to intervene, slapping Ghalib with a restraining order that kept him away from the singer and her family until 2012.
Jason Trawick (2009-2013): The Hollywood love agent
Britney Spears’ ex fiancé Jason Trawick was telling her what to say through an ear piece on the X Factor, according to Sharon Osborne. pic.twitter.com/uit9GHLVN5
— Britney Stan ✨ (@BritneyTheStan) August 6, 2023
Jumping ahead to 2009, Britney found herself another leading man, Jason Trawick, a Hollywood agent strutting his stuff at WME. Love blossomed, and they decided to make it official by getting engaged in December 2011. Unfortunately, the happy ending didn’t quite pan out, as they chose to part ways after two years in January 2013.
In a heartfelt statement delivered by her representative to ABC News, Britney shared, “Jason and I have decided to call off our engagement. I’ll always adore him and we will remain great friends.” Trawick chimed in with his own statement, saying, “As this chapter ends for us, a new one begins. I love and cherish her and her boys, and we will be close forever.“
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David Lucado (2013-2014): The legal eagle
Just two months after calling it quits with Trawick, Britney found a new boyfriend in David Lucado, a man who worked at a legal firm. Their love story didn’t have a long shelf life though, and in August 2014, Britney tweeted her newfound single status, exclaiming, “Ahhhh the single life!” Her representative confirmed the news to People, stating “Yes, she’s single.”
Ahhhh the single life!
— Britney Spears 🌹🚀 (@britneyspears) August 28, 2014
But the breakup took an interesting twist when TMZ alleged that Lucado had strayed from the path of loyalty. The bombshell? Claims that Britney’s father had obtained a video of Lucado’s alleged infidelity. Lucado, however, refuted the cheating accusations, asserting that he was only seeing the other woman during their split.
Charlie Ebersol (2014-2015): Britney’s techie boyfriend
The next name on the list of Britney Spears’ boyfriends is the co-founder of Tempus Ex Machina and The Company who strolled into the singer’s world in 2014. Their romance may not have garnered as many headlines, but it had its own unique charm. In Britney’s words, “There was something about him that made me feel really peaceful and at ease. And he was really hot, too. Adorably hot,” as she confided to People.
However, like many relationships in her life, this one also had a short shelf life and the two officially parted ways in June 2015 after eight months.
Sam Asghari (2016 to 2023): The longest love
The most recent, and also the longest, partnership that Britney has had is with actor Sam Asghari.
They first met in 2016 and embarked on a love story that has been filled with both joy and heartbreak. Their journey began when Asghari starred as Spears’ love interest in her music video for ‘Slumber Party’ from the album Glory. The couple made their relationship public on Instagram in 2017, standing as pillars of support for each other during significant moments, such as the GLAAD Media Awards where Spears was honoured with the Vanguard Award for her advocacy for LGBTQ equality.
The couple shared the news of Spears’ pregnancy in April 2022, marking their first child together and Spears’ third. Tragically, however, a miscarriage shattered their dreams of becoming parents, a loss they mourned publicly. Despite this heartbreak, they celebrated their love with a grand wedding in June, surrounded by celebrity friends like Selena Gomez, Paris Hilton, Drew Barrymore and Donatella Versace.
However, their relationship faced turbulence later that year. Amidst rumours of infidelity, Asghari filed for divorce in August 2023, bringing an end to their six-year journey together. In a heartfelt statement, he expressed their mutual love and respect, urging kindness and understanding from the public and media alike.
As the world is anticipating Spears’ memoir, The Woman in Me, Asghari, who has read an early copy, stands by her side, expressing pride in her courageous storytelling. In an interview with TMZ on 13 October, he explained that he wasn’t worried about anything being written in the book that could paint him in a negative light. “She put a lot of work into it, and it was very hard. I’m definitely excited, and I’m extremely proud of her. It was a very tough one [to write].” he told the outlet.
Despite the challenges, he has affirmed his unwavering support, highlighting the strength and determination she displayed while writing the deeply personal book.
The Woman in Me will be published on October 24 in the US and UK.
(Header and feature image courtesy: Credits: Instagram/Britney Spears)
