Dating as a superstar pop princess is not easy, and Britney Spears knows that all too well. Catapulted to international fame as a young and inexperienced 17-year-old meant she also had to navigate dating in the spotlight. That came with its unique set of challenges, as is obvious from her complicated dating history…
A tumultuous life in the limelight
Britney Spears rose to fame in the late ’90s with her breakout hit Baby One More Time, and for the following decade she dominated both the pop music scene and the tabloids. But even though she has been immensely successful professionally, her chaotic romantic relationships and personal life hint at something more complex going on behind the scenes.
New information has come to light recently, for example through the new documentary Framing Britney, showing just how challenging Britney’s life and relationships have been.
The Britney and Justin era
Britney’s first love and first serious relationship was also very much high-profile. We’re of course talking about Justin Timberlake. These two basically grew up together, as members of the popular Mickey Mouse Club, and both these talented singers reached superstar level fame in their late teens.
For a while there, they were the cutest young couple in the music industry, and seemed made for each other. Sadly, that image of their romance would not last too long.
Heartbroken for the first time
Justin and Britney dated for three years, but in 2002 they split – which seemed to break Britney’s heart more than Justin’s…
Britney has always been fairly tight lipped about her personal life, but she did admit in interviews she was hurting from the breakup. She also said she was struggling to move on with just “some other guy”, as she’s the type of person who’s really serious about her relationships, and can’t just jump to the next random person.
How the media seemed to look at it
Even though Britney was clearly sad and distressed over the ending of her first big love, the media and the world did not show much sympathy for her. Instead, the harsh tabloid climate which dominated the late ’90s and early 2000s, meant Britney was under more scrutiny than ever.
Soon enough, damaging rumors about her character, and the reason for her and Justin’s breakup, started swirling around. And this was made even worse by the fact that Justin helped fuel them…
That music video…
While their break-up started a downward spiral for Britney, it basically helped propel Justin’s solo career to greater heights. Cry Me A River is to this day one of his biggest hits, and it was as obvious then as it is now – the lyrics and that music video heavily imply that Britney was the inspiration behind the song.
The fact that it was released in 2002, the same year they broke up, the fact that the woman in the music video looks and dresses exactly like Britney, the fact that the lyrics talk about not forgiving a cheating partner…none of it made Britney look very good.
An apology, 19 years too late
Because of the recent documentary Framing Britney, which shows how unfairly Britney was portrayed in the media starting from the time of this break-up and basically up until very recently – Justin wrote an official apology on his Instagram.
Even though he acknowledged and apologized for his part in damaging Britney’s reputation and career, that apology is around 19 years too late. It can’t change the many tumultuous and damaging choices and relationships a struggling Britney embarked on after their break-up.
On the rebound
It’s a move as classic as it is cliche; sweet, young girl loses her innocence to the seemingly nice boy who breaks her heart, and moves on to an obvious bad boy. Perhaps Britney felt like she might as well act bad, since that’s how the world saw her anyway.
In 2003 she was linked to Fred Durst, the too cool for school frontman of the at the time popular nu metal band Limp Bizkit. This was yet another relationship that would not work out in Britney’s favor.
Not exactly a gentleman
After first hinting at having genuine feelings for Britney, and saying anyone who had a negative opinion about their relationship should mind their own business – just a month later Fred Durst was singing a very different tune.
Suddenly he was talking about her in a much more crude way in interviews, saying they had just shared a casual fling while working together because he finds her attractive (we are phrasing things more respectfully than he did…)
Trying to stay above it all
Britney was mature and classy enough to not stoop to Fred’s level. Through her representatives, she just released a statement saying she found it unfortunate Fred Durst would make up these kinds of rumors, and that the whole situation seemed very “junior high school”.
Britney never confirmed what kind, if any, relationship she had with Fred. But yet again, she was being judged for her rumored love life (and the nature of it), whereas Fred wasn’t judged at all for talking about private matters so inappropriately in public.
A fling with an Irish actor?
No one really knows what happened between Britney and Irish actor and charmer Collin Farrell, but there’s plenty of cute and cozy pictures of them at the premiere of his 2003 movie The Recruit.
There’s also some rumors about them sharing a romantic kiss at the Chateau Marmont hotel in West Hollywood, after the screening. But Farrell, clearly more of a class act than Fred Durst, swore him and Britney were just friends, and at that these rumors ended.
Dating one of her dancers
Columbus Short, to most known from Scandal, used to be one of Britney’s backup dancers back in the day. And the two seemed to be getting really close around 2003 and 2004. Short even admitted to the two having amazing chemistry, and having slept in the same bed.
Again, no word from Britney herself about this, but there are plenty of paparazzi pictures of these two hanging out, and looking too cozy for people who are just friends and co-workers.
A married man
The problem with this romance, is that Short was actually married at the time, and his wife was pregnant when this story came out to the public, making for yet another scandalous Britney dating story.
According to Short, Britney’s mother Lynn put a stop to the relationship before it could get too far. It had still gone far enough for Short’s wife to divorce him, and in interviews he said Britney caused problems in his marriage, he still has great memories from their time together.
Another dancer
During the early 2000’s, when Britney’s star was still shining very bright, she apparently had another fling with someone she worked plenty with during these years; the renowned dancer-choreographer Wade Robson.
Everyone who was anyone on the pop music scene wanted to work with Wade back in the day, and him and Britney teamed up plenty, for example for her You Drive Me Crazy music video. Wade conformed the fling between the two in 2015, but we have not heard Britney’s version for this relationship either.
Struggling to juggle it all
In hindsight, it’s easy to see Britney was seriously struggling those first intense years of her career, after the traumatic break-up with Justin Timberlake. She was working hard pumping out hit after hit, touring, and casually dating – and the media scrutinized her for all of it. But none of her flings seemed very serious, or very successful.
Britney was quickly learning that finding a guy who loves you for you is easier said than done when you’re a superstar. Perhaps that was why she turned to her childhood friend, Jason Allen Alexander.
Tying the knot for the first time
The whole world was perplexed when it suddenly came out Britney had married some dude no one had ever even heard of before. After a wild New Year’s party, her and her old childhood pal Jason decided to spontaneously get married in Las Vegas.
It seems as if Britney was sick and tired of all the famous and superficial men in her life, and for a moment thought marrying someone who knew her before she was famous, was the solution.
It didn’t last long
Britney and Jason got married at 5 a.m. on January 3rd, 2004, so just the hour they got hitched says something about how thought through the decision really was…
After just 55 hours, they had the marriage annulled. Jason has since stated she’s the one who proposed to him, and that he just went along with it in the heat of the moment – but that he was indeed in love with her. He had been under the impression she felt the same, but that’s hardly how Britney described it.
Feeling rebellious
Later in interviews, Britney would say marrying Jason was done at a time when she was feeling rebellious. They had been partying, and she hadn’t really been thinking too much about her actions.
Many do refer to 2004 as Britney’s “wild year”, a year when she was trying to break free from her innocent girl next door look perpetuated by her manager and label. But Britney also recognized she was rebelling to try to run away from soemthing, although she didn’t know quite what.
Doing much better, but…
Britney claimed she was doing much better after her spontaneous and short-lived marriage to Jason, and that she enjoyed being single for once, and figuring out who she really is. But that was short-lived.
Barely had she annulled her first marriage, before she was jumping into another serious commitment, seemingly way too fast. She met dancer Kevin Federline in April of 2004, and even though he had a baby on the way with his very recent ex-fiance, the two were taking things to the next level already by July.
A whirlwind relationship
Britney and Kevin got engaged in July, and tied the knot on September of 2004. What followed was an intense whirlwind of a marriage, which lasted longer than Britney’s first – but short enough to hint at this being yet another mistake…
Britney was a few months away from turning 23 at the time of her nuptials, and had known Kevin for all but five months. The fact that she was in such a hurry to get married so young, with someone she barely knew, says something about her need for security and roots in her hectic and drama-filled life in the spotlight.
Starting a family
Not only did they get married quickly, Britney and Kevin also decided to start a family immediately. Almost to the day a year after they tied the knot, on September 15th 2005, their first son Sean Preston was born. And almost to the day a year after that, on September 12th 2006, baby boy number two Jayden James arrived.
In other words, these couple of years were crazy intense for Britney. She had her hands full with two toddlers, and at the same time was still a young woman grappling with fame, and learning how to navigate marriage. And things didn’t seem to be going great.
Filing for divorce
By November 2006, with a two-month-old and a 14-month-old in tow, Britney filed for divorce. She cited irreconcilable differences, but Kevin expressed concern over Britney’s mental state and wanted primary custody of their babies.
In hindsight, both have admitted the marriage was a mistake – especially Britney. She said in interviews a few years later she regrets the marriage, and that she did it more out of the idea of being married, and becoming a young mom, rather than true love and compatibility.
A downward spiral
It was around the time of the divorce, that things really started to spiral out of control for Britney. The toll of the past almost decade in the limelight, and her whirlwind two-year-long marriage, started catching up with her.
Now it also started affecting her career. Britney started partying a lot, behaving erratically, and showing the paparazzi sides that made the entire world think she was not healthy. But the media’s coverage of her struggles, was part of the problem.
The reason for that breakdown
We’ve all seen the dramatic tabloid pictures from Britney’s infamous so-called breakdown in 2007. One late night in February, Britney headed to a hair salon and got her head shaved – in front of dozens of shocked paparazzi. But that wasn’t all.
She then proceeded to lash out and attack one of their cars with an umbrella. Britney was fed up with being stalked and harassed, but she was mostly under a lot of stress due to the custody battle over her children.
Going to rehab
In early 2007, Britney spent a month in rehab to try to get back to a healthier place. At first she left after just 24 hours, for unclear reasons. It’s around this time she had her very public breakdown. However, soon after she returned to rehab, as Kevin as threatened to pursue sole custody if she didn’t finish treatment.
So Britney went back and completed a month-long stay. But things continued to be shaky over the following two years, both in Britney’s personal life and her career.
That 2007 MTV Music Awards performance
Britney’s career had seriously taken a hit at this point in time, and in 2007 she attempted a sort of comeback by doing her first broadcast performance in three years at the MTV Music Awards.
She had a new song out, Gimme More, which wasn’t doing too well compared to her older hits, so it was an attempt to revive her career. But the entire performance was a disaster. Britney appeared confused, lethargic, and as if she didn’t even want to be there. Her usual magnetic scene presence was nowhere to be seen.
Tearing her to pieces
The media tore Britney to pieces over her performance, and even body-shamed her for not being as thin as she was a few years earlier (ignoring the fact that she had had two kids back to back fairly recently, and that she was far from overweight).
It seemed as if headlines around Britney at this time all framed her as crazy, rather than showing some sympathy and respect for a young woman struggling in her personal life for valid reasons.
Looking for love yet again
In between all the drama of 2006 and 2007, Britney did also jump back into the world of dating. But as a newly divorced mother of two, things were complicated.
She allegedly had a brief fling very soon after her divorce, with the model Isaac Cohen. But that ended in February of 2007, before Britney’s stint at rehab and her public meltdown. Reps for both parties stated the two were both busy with their careers, and that Britney was too preoccupied with her divorce dealings and with taking care of her kids, to be able to invest in a new relationship.
Meeting in rehab
Britney was even rumored to briefly date a fellow struggling star whom she met in rehab; singer Howie Day. Perhaps the two bonded over their respective struggles, but it’s unclear how serious it was.
The two were spotted together a couple of times, and unfortunately for Britney an ex-bodyguard of hers fueled (or maybe even started) the rumors about this fling. Howie has not addressed the relationship, more than in 2013 acknowledging he lived a pretty wild, bad boy lifestyle in his mid-twenties, and that he’s thankful to be past it.
From paparazzi to boyfriend
Britney’s longest relationship during her turbulent rollercoaster 2007, was with paparazzi photographer Adnan Ghalib. The two dated for around a year, but ended with Britney filing a restraining order against him.
During their relationship, Adnan frequently gave away Britney’s location to the press, and Britney even suspected he was trying to get his hands on her money. However, it’s unclear if the restraining order was really Britney’s wish, or her father’s. Jamie Spears got Britney placed in a conservatorship in 2008, which means he controls much of her decisions.
That alleged fling with Mario Lopez
Television host and former Saved By The Bell star Mario Lopez also had a short fling with Britney sometime in the mid 2000’s, but the details are a little fuzzy. Neither him nor Britney have confirmed this alleged fling.
But Mario mentions in his 2014 memoir Just Between Us, that he had a one-night stand back then with a “mega pop star.” There are also some pictures of the two looking pretty cozy, both on and off the red carpet.
Dating the manager
In the beginning of 2009 things were starting to look up for Britney. She was mid-way through her comeback, with songs like Circus, If You Seek Amy, and 3 topping charts. And, she finally seemed to have found a more permanent, serious relationship.
She started dating Jason Trawick, her former manager, in early 2009, and suddenly Britney was no longer causing headlines because of excessive partying or dating. The two seemed very solid, and Britney seemed happy for the first time in a long time.
Calling it off
Jason and Britney were still going strong almost three years later, when Britney in December of 2011 announced the couple’s engagement on Twitter.
However, even though they had a great, solid relationship for years, the two together decided to call off the engagement in January of 2013. But, they never talked badly about each other, and stated they were still good friends. It seems as if the split was mostly due to wanting different things in life. Britney for one wanted more children, and Jason did not.
Stepping away from famous boyfriends
Britney and Jason had been slowly growing apart for several months up until their split, so that’s probably why Britney was ready to date again pretty soon. Not to mention she was in a happy and healthy place in her life, both personally and professionally.
On Valentine’s Day of 2013 she was spotted on a date with David Lucado, a legal office employee. The pop princess and the regular guy from Virginia made an adorable couple. And it was a refreshing change for Britney to date someone from outside of the fame bubble.
Gushing to Ellen
Britney gushed about her new beau when she appeared on The Ellen Show in December of 2013, and also revealed the two met at a party. She was drawn to his confidence and his sense of humor, as well as to how comfortable and friendly he was also around someone famous like herself.
And childhood friends of David’s admitted they were not surprised at all the star had fallen for him, as their friend was the kind of guy who always got the best girls.
Heartbroken, yet again
Britney and David lasted for a year and a half, which is a pretty impressive run considering mixed famous and non-famous couples tend to struggle. But, it was not Britney’s superstar status that caused problems in this case. Instead, David cheated on her and broke her heart.
In September of 2014, a month after the breakup, Britney was still heartbroken (and angry!) enough to rat him out in front of her audience at Planet Hollywood, where she was a resident performer from 2013 to 2017.
Not letting herself get beat down
Even though Britney was sad and hurt by the breakup, she was now at 33 a lot more resilient, and used to bouncing back. And luckily, her career was yet again in a good place, so she could channel her energy into putting on a great show at Planet Hollywood.
She was also in a good place with her baby daddy Kevin, and the two were by now amicable and supportive co-parents to their two boys.
Bouncing back
By November of 2014, Britney had already rebounded, and seemed to have found another charmer; TV producer and director Charlie Ebersol. He’s most known for being the executive producer of USA Network’s NFL Characters Unite.
Britney and Charlie had a whirlwind romance, and Brit even started wearing a “I Love Charlie” vest on her Vegas shows. She also brought him as her date to Billboard Music Awards in 2015. But, the two broke up in June of 2015.
Finally the real deal?
Britney then took a pretty long, and probably well-needed break from dating. Only in 2016 was she linked to a new beau, and this time one much younger than her.
Sam Asghari is a model 13 years Britney’s junior, but despite the big age gap the two hit it off right away. The two met in 2016 at the set of the music video for Brit’s Slumber Party. Sam plays her love interest in the music video, and the chemistry was clearly very real.
Taking her time
In 2017, Britney recalled in interviews how her and Sam had bonded in between takes of the music video. But, even though she got his number, she forgot about the encounter at first.
Five months later, she suddenly found the note with his number in her bag, and remembered how cute and funny she thought that guy was. So she decided to give Sam a call, and he was immediately up for a date. It wasn’t long before the two were spotted together everywhere, and he was her date to every event.
Still going strong
Many thought Sam was just a casual fling at first, partly because of the age difference. But today these two are still going strong. Sam works as a personal trainer, and the two often post cute Instagram pictures and videos of them hiking, working out, or just goofing around. And they seem genuinely happy together.
Considering all the drama Britney has gone thorough over the years, and with the on-going controversy considering her conservatorship, she deserves to have someone who’s loyally standing by her side through it all.
