Who Has Britney Spears Dated?

Britney Spears has been famous since she was just 16 years old — or even longer, if you count her Mickey Mouse Club days. As a result, her dating life has always been a hot topic.

When it comes to celebrity love life milestones, Spears hits them all. She had an ill-advised quickie Vegas marriage. She hooked up with Fred Durst, arguably the girlfriend-hopping Pete Davidson of the '00s. And she even followed the age-old pop star tradition of dating a backup dancer!

After Spears' controversial conservatorship came to an end, she's looked forward to marrying Sam Asghari, the model and personal trainer who loved to call her his "lioness" on Instagram. Spears was hoping to have kids with Asghari, as the two seem inseparable, but the pair ultimately didn't ride off into the sunset. And with her new tell-all memoir that dishes on Justin Timberlake, what better time is there to take a look back at Spears' headline-grabbing dating life?

First love Reg Jones

Not even Britney Spears' high school relationship stayed totally private. Her former boyfriend, Donald "Reg" Jones, allowed two letters she'd written him to be auctioned off in June 2021, per Yahoo!. One of the letters actually has Spears gently dumping Jones.

"Look, I'm really sorry that it had to be this way, but I think we both knew this was coming," the compassionate queen wrote, per Yahoo!. "I've had a great two years. Who knows, two years from now or even 10, we might get back together if it's meant to be."

Despite cashing in on her letters, Jones only had great things to say about the pop star and was still pining for her post-breakup. "She was the love of my life," he told the New York Post in May 2021, adding, "I don't go around wishing we were back together ... I wish her the best in all that she does."

Justin Timberlake

Back in the 2000s, Britney Spears and Justin Timberlake were the couple everyone was talking about. Their relationship had it all: chart-topping music, of-the-moment fashion, and yes, creepy speculation about Spears' virginity from the public. People loved them.

They dated from 1998 to 2002, splitting when Timberlake suspected Spears of infidelity. But the breakup did nothing to dampen media interest in them — especially because Timberlake cast a Spears lookalike as the cheating girlfriend in the music video for "Cry Me a River." He also repeatedly made jabs about her, resurfaced in 2021's "Framing Britney Spears" documentary — including the time he joked about sleeping with her on the radio, per BuzzFeed.

After outcry from Spears' fans, Timberlake posted an apology on social media. ​​"I am deeply sorry for the times in my life where my actions contributed to the problem," he wrote, "where I spoke out of turn, or did not speak up for what was right." Spears didn't publicly respond, but she did mention a happy memory of their time together a few months later. Spears referenced a song of his on Instagram, saying, "I know we had one of the world's biggest breakups 20 years ago ... but hey the man is a genius!" Queen of handling breakups with class.

Wade Robson

At the height of Britney Spears' 2000s fame, there were rumors that she'd flirted with everyone from Prince William to Ben Affleck. Most of these claims have died down in the years since and may have been complete fabrications. But one rumor that's persisted involves Spears and the famous choreographer (yes, in the Y2K era we had famous choreographers) Wade Robson.

Robson worked as a choreographer for Spears' "I'm a Slave 4 U" and "Oops ... I Did It Again" music videos, per Decider, and was known as the "sixth member" of Timberlake's group, 'NSYNC. No one involved has commented on the rumors that Robson and Spears' relationship became intimate. But Robson's professional relationship with Spears and 'NSYNC fizzled out right after Spears and Timberlake's breakup.

Robson's name was in the news again after the release of the documentary "Leaving Neverland," in which he accused Michael Jackson of abusing him as a child, according to Forbes. A case he filed against Jackson's estate was thrown out in April 2021, and it's unclear whether he will continue to pursue legal action, per EW.

Fred Durst swears they had a fling

Limp Bizkit's brand of angry white boy alt-rock-rap might not have stood the test of time, and it's unlikely most Gen Zers even know who frontman Fred Durst is. But Durst capitalized on the band's chart-topping 2000s fame by linking himself to as many pop stars as he could, whether or not they wanted him to. And one of those performers was Britney Spears.

In 2003, Spears was single and fresh off of her breakup from Justin Timberlake. Legend has it that Durst and Spears linked up at the American Music Awards that year. Durst wrote in a blog post on his band's website (seriously!) that he'd "never felt this way," according to Today. He even swore they'd hooked up on Howard Stern's radio show.

But Spears maintained that there was nothing to the story. "He's said some pretty amazing things about me. But, um, I think he leaped in too deep, too quick," she told Glamour UK, via Today. So where is Durst now? He dabbled in hosting jazz nights in 2017 and claims the band is still together. "I still perform and manage Limp Bizkit," he told LA Weekly. "We're very selective of where we play." Yeah, that's why we never hear from them anymore. Okay, Fred!

Colin Farrell

Britney Spears never confirmed her fling with Colin Farrell either, but at least there's photographic evidence of them hanging out. During the early 2000s, the Irish actor reportedly cozied up to Michelle Rodriguez, Angelina Jolie, Lindsay Lohan, and Carmen Electra, per W, just to name a few.

Spears and Farrell held hands at the movie premiere for "The Recruit," according to People. "She's just a mate," he said at the time. "Seriously, we just met a week ago, [we're] having a laugh." They were spotted making out at L.A.'s Troubador club a few days later, but Spears' publicist still insisted they were just friends.

Their appearances together fizzled out. But according to one report, he sent her a few souvenirs, including a T-shirt emblazoned with, "I slept with Colin Farrell and all I got was this lousy T-shirt," per The Daily Edge. Wherever the truth lies, one thing's clear from the photos alone: they had a great time.

Columbus Short

Britney Spears allegedly had another fling with a choreographer in 2004. Columbus Short, who has since transitioned to acting, worked on Spears' Onyx Hotel tour. One night, Spears chartered a jet for him and the other dancers to fly to New York City, he wrote in his memoir, "Short Stories," per Hollywood Life.

They ended up at a party at Keith Richards' apartment, of all places, where the "Scandal" and "Stomp the Yard" actor says Spears was on him "like white on rice," per Hollywood Life. "I really tried my best, but this girl put on the full-court press," he wrote. "We ended up being intimate that one time. I never slept with her again after that, though. This was a dangerous sexual alliance for every reason under sun."

Short also revealed that he heard Spears' parents use a racial slur to describe him while Spears had them on speaker phone. "Britney looked at me so apologetically, knowing I'd heard it," he wrote, per Page Six. "I shook my head and didn't say anything, because what was there to say?" Just one more thing to add to the Spears parents' list of stellar accomplishments.

Jared Leto

The year after Britney Spears and Justin Timberlake broke up, Timberlake was spotted with Cameron Diaz. The two would date from summer 2003 until 2007, becoming a Hollywood "it" couple in their own right until each of them moved on to their current spouses, Jessica Biel and Benji Madden.

But when Timberlake and Diaz's relationship was in its infancy, Spears set tongues wagging by being photographed with Diaz's ex: Jared Leto. According to Contact Music, the pair were spotted together at the Los Angeles eatery Dolce. "Britney is upset about seeing Justin looking so close to Cameron," a friend told the publication. "She really enjoys Jared's company but they were wary of the attention they would get considering who their old flames are."

They pair never publicly commented on their relationship, so whatever went down, we'll never know. Britney needs to tell us her thoughts on Leto's performance as The Joker. The world needs this information.

The short marriage to Jason Alexander

Britney Spears' love life went from fun and games to WTF on New Year's Eve in 2004. That's when she decided on a whim to marry high school pal Jason Alexander at the famed Little White Wedding Chapel in Las Vegas, Nevada, per ABC News. It only lasted 55 hours because when Alexander and Spears broke the news to their moms, "everyone went crazy because there was no prenup," he said.

The quickie marriage and annulment dominated the news even more than Kim Kardashian's day-72 divorce from Kris Humphries would seven years later. Alexander claims that Spears' people said they could get married for real if they were still dating six months later, according to ET Canada. He agreed to the annulment on the grounds that they'd keep dating. But he claims that as soon as the annulment went through, he never heard from Spears again.

Still, Alexander maintains that he really was in love with the pop star. When asked what he learned on "20/20," he said, ​​"Don't be a nice guy. Nice guys finish last. Look out for yourself. If you are going to really get involved into a relationship with a celebrity and you are just an average Joe, make sure you are thinking business!" Yes, sounds like he was totally in it for the right reasons, nothing suspicious at all.

Husband no. 2, Kevin Federline

A few months after Britney Spears' ill-fated union with Jason Alexander, she gave matrimony another shot with Kevin Federline, a backup dancer with whom she seemed to have fallen madly in love. Most millennials will recall their MTV docu-series, "Britney and Kevin: Chaotic," as the definitive portrayal of love in the age of the flip phone.

The couple married in 2004 (they iconically clad their entire bridal party in matching Juicy Couture tracksuits) and had two children, Jayden James and Sean Preston. But Spears filed for divorce in 2006, and their split was finalized in March 2007, per Us Weekly. The resultant custody battle over their two sons is cited as a major factor in Spears' troubles that year.

More than a decade later, Spears and Federline are said to be on decent terms, with Federline reportedly supporting Spears' quest to end her conservatorship, per The Daily Beast. Still, some fans think there's evidence that Federline and his lawyer, Mark Vincent Kaplan, haven't always acted in Spears' best interests.

Adnan Ghalib

The year 2007 was so rough for Britney Spears, it spawned a modern-day aphorism: "If Britney Spears could make it through 2007, you can make it through today." Spears shaved her head in February of that year as the custody battle over her sons raged on. She became a punching bag for the general public and the butt of many jokes.

In the middle of it all, paparazzi photographer Adnan Ghalib started dating Britney Spears. Ghalib says he and Spears hit it off when he showed her how to use a gas pump while the rest of the paparazzi just shot photos of her struggling to gas up, and there's even video footage of the moment. He claims he kept her company during three-day Adderall binges and other stressful times. "What was apparent during that time is that she never had one person she could trust, not mum, dad, friends, or sister," he says in the Netflix documentary "Britney Vs. Spears." "Nobody."

That documentary implies that Spears' family's discomfort at her dating Ghalib contributed to her conservatorship being put in place. But The Daily Beast calls him a "rogue paparazzo" who made her "life a living hell" and even shopped around a sex tape of the star. We'll never know the truth, unless Spears decides to set the record straight on her own.

Agent Jason Trawick

After a few turbulent years, Britney Spears appeared to be settling down long-term again when she started dating her agent Jason Trawick in 2009. The world learned they were an item at the Grammy Awards in 2010 when they showed up holding hands, per MTV. 

They were serious enough that they decided to stop working together professionally to avoid any conflicts of interest. They became engaged in 2012, per Today, and seemed pretty normal: "He says he doesn't mind that I sit around in sweats all the time," Spears said. They parted ways in 2013 because they both wanted 'different things,'" according to People.

In fact, some #FreeBritney-affiliated sleuths think Spears and Trawick really did tie the knot. When combing through conservatorship paperwork, the hosts of the podcast "Toxic: The Britney Spears Story" found something slightly fishy, per The Sun: a bill for "dissolution of marriage" filed in California as part of Spears' ongoing legal drama. Spears also referred to Trawick as her "husband" in an interview during their engagement. Trawick denied to Extra! that he and Spears were ever married.

David Lucado

Three months after Britney Spears' engagement to Jason Trawick dissolved, she moved on with David Lucado, a former bartender working in field research at a law firm who she'd met through friends, per TMZ. "He's definitely not a wealthy guy," the gossip site helpfully added.

InTouch tracked down Lucado's aunt, Gayle Lucado, and she assured the magazine that he was a stand-up guy. "​He's a true Southern gentleman and I could never see him doing anything to hurt her," she said. Even Spears' ex Kevin Federline was singing the guy's praises, telling TMZ he was friendly with Lucado.

Well, Auntie Gayle and K-Fed must have jinxed it. About a year and a half after news of their relationship broke, TMZ got word that a video of him making out with someone else was floating around. Spears' father reportedly purchased the footage to keep it from going public. And Spears capped off the whole saga by tweeting, "Ahhhh the single life!" You have to hand it to her: she's always kept her sense of humor intact.

Charlie Ebersol

In 2015, Britney Spears started dating Charlie Ebersol, the producer friend of her assistant, according to People. On their first date, Spears told People, "I said, 'Cook for me!' So he made fish, mushrooms, avocado with a dressing, and tomatoes, and mozzarella. It was amazing."

They kept dating for eight months, with Ebersol gushing to People that Spears had an "enormous heart," but then their relationship abruptly ended, with Spears wiping all mention of him from her social media accounts, Us Weekly pointed out.

Rumor has it that Jamie Spears caused their split because he didn't want Ebersol "dismantling the work" he'd done. Yes, seriously. "Jamie doesn't want Britney getting married again. He doesn't want a man coming in and dismantling the work that he and others have done to get Britney in the place where she is now," a source told HollywoodLife. "[Jamie] simply talked to Britney. He reminded her of her past and warned her what could happen if she were to marry Charlie." Bleak.

Sam Asghari

After the David Lucado and Charlie Ebersol breakups, Britney Spears found longer-term love with model and personal trainer Sam Asghari. Asghari proposed to Spears in September 2021 after five years of dating, according to the LA Times.

Perhaps the most heartbreaking detail of Spears' conservatorship saga involves her desire to have children. Spears testified in August 2021 that her conservators wouldn't let her remove her IUD birth control device so that she could have children, per The New York Times. "I want to be able to get married and have a baby," she said. "I was told right now in the conservatorship I am not able to get married or have a baby."

Spears and Asghari announced they were engaged with an Instagram video shortly after delivering that testimony, in addition to Spears' father being removed as her conservator. Sadly, the pair split in 2023 after only one year of marriage (via E! News). When asked about his loving namedrop in Britney's new memoir, he had nothing but great things to say about his estranged ex-wife. "I hope she takes over the world," he told TMZ.