Justin Timberlake
Weren't these two just a little slice of everything while they lasted? The pop princess and the boy band heartthrob came of age, tween star style, on The Mickey Mouse Club and made for the most inevitable of couples. Justin was even Britney's first kiss. Young, innocent love at its finest.
Until 2002, that is, when they unceremoniously split up.
Rumor later had it that Britney cheated on Justin, prompting him to exorcise those demons with his solo hit "Cry Me A River."
Brit, however, seemed pretty heartbroken, regardless of what happened. She reportedly told The Sun, "I'm still hurting but I am trying to see it as an experience. The worst thing is everyone wants to talk to me about it. Everywhere I go people are asking how I am." Asked if there were any immediate prospects in her life, she added, "I'm the type of person who can't go from a serious relationship and then just start dating someone else straightaway. It's a strange feeling getting used to being single again, but I suppose I'll have to cope. I'm just starting to get the knack of it because ever since I was 15 I've been in a serious relationship."
As big a star as he was already, it wasn't until after the unraveling of this relationship that Justin came into his own, either.
"The breakup was absolutely heartbreaking for me," the then-21-year-old singer admitted to The Telegraph in September 2002. He continued, "I can't just have meaningless relationships with women. I have to find Miss Right in order to have a relationship. There's got to be that big moment when she comes along."
A sentiment that sounded ironically familiar.
Fred Durst
When they were first rumored to be dating in January 2003, the Limp Bizkit frontman wrote on his band's website, "Anybody out there who has a serious problem with my feelings for Britney should just chill and worry about your own feelings for a minute. You can't help what happens in life because everything happens for a reason. I believe that."
The next month he told Extra they weren't dating, chivalrously saying, "Hell, no. She's got a great ass, that's all."
Just weeks after that, he told Howard Stern he had hooked up with Britney while they were working on music together and she was doing him wrong by denying it. Graphic details ensued.
"It's sad that he's decided to make up stories, and the situation feels very junior high school," Britney's rep said in response to the interview.
Reflecting on the he-said, she-said in 2009, Fred told MTV News, "It just became a fiasco of madness. [But] I always stay true to my heart and true to everything I did and my intentions, and I am in no way a liar...I just guess at the time it was taboo for a guy like me to be associated with a gal like her."
Colin Farrell
She may not have been up for casual dating, but a casual encounter with the roguish Irish actor? Who could blame a girl?
"We're just mates and we're not dating," Colin insisted, though that didn't put a damper on some cozy-looking sightings and Spears' presence at the premiere of his 2003 film The Recruit. People reported at the time that they were seen kissing on a balcony at Chateau Marmont after the screening.
Columbus Short
A decade before he joined Scandal (and then scandalously got arrested and left the hit drama), Columbus was one of Britney's backup dancers—and though they never consummated their relationship, they were allegedly close.
"It's true I slept with Britney, [but] we never had sex because another person was in the room at the time," he reportedly told the U.K.'s Star magazine in 2004. "We shared a bed and were really close, kissing and hugging. The chemistry was magical…our feelings were so strong...Britney's mom, Lynne, stepped in to prevent that as soon as our feelings started to develop."
Alas, Columbus was married at the time and his wife was pregnant when this all came to light. "It would be fair to say Britney caused major problems in our marriage," the dancer-actor said. "Sadly, we're now getting divorced." But "despite everything that happened, I'll always remember those special moments with Britney."
Wade Robson
Also sometime in the early '00s, Britney is rumored to have hooked up with the famed dancer-choreographer, who appeared in her "(You Drive Me) Crazy" video.
"That's true," choreographer and Stomp the Yard star Darrin Henson said on Sway in the Morning in 2015. However, Britney and Wade haven't confirmed what happened.
Jason Allen Alexander
On Jan. 3, 2004, she thought marrying her childhood pal Jason "Not of Seinfeld Fame" Alexander in Las Vegas seemed like a grand idea.
After some New Year's partying that included sharing a kiss with one of her female dancers and flying Alexander into town from Louisiana via private jet, at around 5 a.m. Britney and Jason tied the knot. Though no one had ever heard of this dude before that night, in 2012 Alexander told ABC News that he and Brit had actually been FWB back in the day, even when she was dating Justin Timberlake.
So when the singer "was like, 'Well, let's get married'...I was like, 'Sure. You know, let's do this,'" he recalled. "I went with my feelings," Alexander added. "I was in love with her...I feel like she felt the same way."
They were married for 55 hours. The annulment stated that Britney "lacked understanding of her actions, to the extent that she was incapable of agreeing to the marriage."
Britney told E! News in March 2004 that she was just "being silly, being rebellious, and not really taking the responsibility of what I was doing, you know? And after partying, you know, you really don't think about what you're doing. So it was one of those things that were really silly."
She concluded, "I think I was running away from something. I didn't quite know what...I'm still figuring out myself and learning every day. But I think I'm more in a good place. I like being alone, which is good I think. You know, I love reading books. I'm really a quiet kind of person right now. And so it's cool to be back and feel like yourself again."
Kevin Federline
But after having had a taste of marriage, Britney deemed herself ready for another go. She met dancer Kevin Federline in April 2004 and, despite the fact that he was expecting a child with ex-fiancée Shar Jackson at the time, they were engaged by July.
Brit and K-Fed had a marriage ceremony on Sept. 18, 2004 (their union was legalized three weeks later after they figured out their prenup), son Sean Preston was born a year later and son Jayden James arrived a year after that. In November 2006, Britney filed for divorce.
"Instead of following my heart and doing something that made me really happy, I just did it for the idea of everything," she mused in the 2008 MTV documentary Britney: For the Record.
Britney briefly lost custody of their kids in January 2008 when she was hospitalized on a 5150 psychiatric hold, which resulted in her affairs being placed in a conservatorship overseen in part by her father—an arrangement that lasted for 13 years before it was terminated in November 2021.
Her career comeback would take some time, but the pop star made sure to focus on getting well enough to be with her boys again right away, and she and Kevin eventually turned into amicable co-parents. He has since had two more children with wife Victoria Prince and is now a father of six.
"Obviously, things didn't work out the way that they were supposed to [with Britney]," Kevin told Entertainment Tonight in 2016. "But everything's OK, you know, like, life happens."
Isaac Cohen
Britney had a brief fling with the model, which ended in early February 2007, a few weeks before she entered rehab.
"They're both busy with their careers," Isaac's agent Brandi Lord told People at the time. "She just got out of her marriage and she has two kids to take care of. Her plate is full, and the same with him." More bluntly, she added, "They were never getting married. They were having fun together."
Howie Day
The "Collide" singer reportedly met Britney in rehab in 2007 and they were spotted together on at least one occasion that spring—and Brit's ex-bodyguard spun a wild tale about a meet-up in a hotel room to the News of the World.
Asked about his rumored escapades, Howie told The Ann Arbor News in 2013, "I certainly played hard when I was in my mid-20s. There were there moments when I lost my way and was a bad boy, absolutely. You give 24-year-old kid a hit song and too much money, and stuff happens. And then when you do something bad, it does go under a microscope. Thankfully, I am past that. Enough years have passed now that when I think back on it, it all seems pretty shocking."
Yet, he and Britney haven't publicly confirmed the rumors.
Adnan Ghalib
After her conservatorship was established, Britney's parents slapped Ghalib and her manager at the time, Sam Lutfi, with restraining orders, accusing them of conspiring to undermine their authority by sneaking her a cell phone to communicate with them.
Sam sued Britney and her parents for defamation in 2012 and Adnan was called to testify. Asked what it was like seeing Jamie and Lynne Spears in court, he told E! News, "Not good." (Sam's entire lawsuit was eventually thrown out.)
Mario Lopez
The former Saved by the Bell star did not kiss and tell, only writing in his 2014 memoir that he had a one-night stand six or seven years prior with a "mega pop star."
"I'm trying not to give too much away without giving too much away," Mario told Ellen DeGeneres while out promoting the book.
Multiple sources told Us Weekly that Britney was the "mega pop star" in question—and that they were both single when the fling occurred. However, the stars haven't confirmed.
Jason Trawick
Britney started dating the WME talent agent in 2009—he had represented her in the past, but he left WME after 12 years to join Famos LLC.
They got engaged in 2011 and Jason at one point became a co-conservator of her estate. She continued to heal and return to form in the recording studio and on stage. But all the ties that bound were untied when the otherwise nondescript couple broke up in January 2013.
"The situation had been building over time. The best thing for both of them was to say goodbye and move on," a source told E! News at the time, noting the duo's "different goals."
David Lucado
Newly single Britney stepped out for a Valentine's Day date in 2013 with the new-to-L.A., Virginia-born, golf-enthusiast legal office employee.
"I don't think by any means he was looking for someone famous," Knox Higley, a high school friend of Lucado's, told E! News. "It is just not hard to believe [that he's with Britney]...He would walk into the room and pick out the best girl. [Sure enough, Britney told Ellen DeGeneres that they met at a party.] He wasn't really scared of anything or anybody. He was very confident, but not cocky or anything. And he definitely was good to his friends."
Though he did have to deactivate his Facebook page after hanging with Britney, due to the unprecedented amount of attention.
"I just love that he's very passionate and he's funny and he's sexy," Britney gushed about him to Ellen in December 2013. "I don't know...I like him. I just...I love him!"
They broke up in August 2014—and Britney said on stage at Planet Hollywood a month later, "Well, by now everyone knows my boyfriend cheated on me."
But David spoke up on her behalf when The New York Times, investigating the ins and outs of Britney's still-chugging conservatorship in 2016, caught up with him.
"If anyone knew the real Britney, they would know that she would rather be remembered for being the great mother she is rather than the artist she is," he said. "And if anyone could see her interactions with her kids, they would know that there is no need for a conservatorship over Britney's personal life."
Charlie Ebersol
By November 2014 Spears had rebounded with the son of former NBC Sports exec Dick Ebersol (in case his last name sounded familiar) and one of "Reality TV's 50 Most Powerful Producers" according to The Hollywood Reporter in 2012.
Britney took to wearing a vest that read "I Love Charlie" during her Vegas shows and he was her date to the Billboard Music Awards in May 2015. Asked that March if she saw wedding bells in their future, she told Extra, "You never know! Who knows?"
Alas, he wasn't the one and they broke up in June 2015.
Sam Asghari
Britney really did take a break from the Insta-official dating scene for awhile, but then she hit it off with Sam in 2016 on the set of her video for "Slumber Party."
"We were waiting and waiting together for 20 minutes at a time, literally stuck there," Britney romantically recalled the scenario to AMP 103.7 in 2017. "We were forced to talk to each other."
"I kept his number, and it was so weird because it was like five months later that I found his number in my bag," she continued. "I was like 'He was really cute. This guy was really cute!' so then I called him. He is just a really fun, funny person."
The two got engaged in September 2021 after Sam popped the question with 4-carat round-cut diamond ring. The romantic proposal came just a month before Britney's decade-long conservatorship was terminated—something that both Sam and the pop star rallied for. "Britney is very excited to embrace her full freedom," an insider shared with E! News at the time. "She wants a new life with Sam and wants to make many changes. She is excited to move on and close that chapter of her life."
Britney, who had been vocal about wanting more kids amid her legal battle to end her conservatorship, announced in May 2022 that she was pregnant. However, she and Sam shared in the following month that they had "lost our miracle baby early in the pregnancy."
The pair are expected to wed on June 9 in an intimate ceremony in Los Angeles.