A Look At Britney Spears' Dating History

Britney Spears rose to fame in the late '90s, opening for acts like *NSYNC, before becoming a household name. Over the course of her career, Spears has sold millions of albums and has won dozens of awards, including a Grammy. Along with an interest in her music, fans have also been curious about her personal life, and Spears does have an interesting dating history. She's been married three times, has two children, and almost all of her relationships have been very public, from Justin Timberlake to Hesam "Sam" Asghari. 

In August 2023, a source told People magazine that Asghari had filed for divorce from the singer after just one year of marriage. A few days later, Spears uploaded a Reel on Instagram with a caption that read, "As everyone knows, Hesam and I are no longer together ... 6 years is a long time to be with someone so, I'm a little shocked but ... I'm not here to explain why because its honestly nobody's business." This is nothing new for Spears, sadly, who hasn't had the best of luck in the love department. 

Britney Spears' very first brush with love happened when she was just 14 years old. Donald "Reg" Jones was the captain of the football team at Parklane Academy in Mississippi, and was friends with Spears' older brother, Bryan. "She was my best friend as well as my girlfriend," Jones told The Mirror in a 2001 interview, as his ex was taking the music world by storm. "Britney is a fantastic girl. She loved to laugh, she loved to have a good time but she was also incredibly loyal and honest. We used to do all the things normal couples do — go to the movies, eat out, fly kites, go fishing. We loved trying everything," he added.

As is the case for many young lovers, Spears' relationship with Jones didn't last. The two ended up going their separate ways once Spears' career really started taking off, and she hasn't looked back. However, Jones admits that he was totally crushed when the "Piece of Me" singer ended things in 1997 — though he still has nothing but wonderful things to say about her. "She was the love of my life. I don't go around wishing we were back together. ... I wish her the best in all that she does," he told the New York Post in 2021.

Easily Britney Spears' most high-profile relationship, her romance with Justin Timberlake was everywhere in the early 2000s. The duo first met when they were both cast on Disney's "The Mickey Mouse Club" in 1992. About seven years later, they reconnected, and Timberlake asked Spears out. Both mega pop stars at the height of their respective careers, the cameras loved Timberlake and Spears — and the two didn't disappoint. As they walked red carpets together in coordinated outfits (hello, matching denim at the American Music Awards), gave sweet interviews about one another, and simply crushed the game of love, people all over the globe couldn't get enough of these two lovebirds. But everything came crashing down in 2002.

Just about everyone was obsessed with what went wrong in Timberlake and Spears' relationship, but once he dropped the music video for "Cry Me a River," things started making sense. Timberlake strongly suggested that Spears cheated on him. Rumor has it that Spears stepped out on Timberlake with choreographer Wade Robson, though that's never actually been confirmed. Timberlake has played coy whenever he's been directly asked about infidelity in his relationship, but he's also done his best to keep things respectful when talking about his ex. "I was in love with her from the start. I was infatuated with her from the moment I saw her," he admitted to GQ in 2006 (via CBS News). Of course, Spears penned the song "Everytime," which many fans believe is her apology to Timberlake, thanks to one particular line: "And this song's my sorry."

From the rumors that Britney Spears hooked up with Wade Robson while she was still with Justin Timberlake, we bring you the rumors that Spears actually went on to date Robson, who co-directed three of her world tours. Robson is also the man behind the choreography in Spears' music videos for "Slave 4 U" and "Drive Me Crazy." The two reportedly got very close while working together. "I know that he was pursuing her. In my understanding, Justin brought Wade onto the project to do production. That's when Britney and Wade really got closer and began sleeping with each other," Michael Jackson's niece, Brandi Jackson – who also dated Robson – said on a podcast in 2019.

Although Spears and Robson never actually went public, many fans believe they dated for the better half of a year, but the only person who really spoke out about their alleged romance was Brandi Jackson. "I found out Wade cheated on me with multiple woman who he hoped would advance his career. You might know one of them, because it was a huge pop music scandal. Wade is not a victim, he's an #Opportunist," she tweeted in February 2019.

In 2004, Britney Spears shocked the world when she got married in Las Vegas. She had been seeing her childhood friend Jason Alexander and asked him if he wanted to go on a spontaneous trip to Vegas for New Years. While they were in Sin City, Spears suggested they get married. "She just came out and asked me. She was like, 'Well, let's get married.' And I was like, 'Sure. You know, let's do this,'" Alexander told ABC News in 2012. "I went with my feelings. I was in love with her ... I feel like she felt the same way," he added. Both dressed in casual attire, Spears and Alexander exchanged vows at a small wedding chapel and enjoyed just a few hours of married life before Spears' team found out about the nuptials and went into panic mode.

On the July 13, 2021, episode of the "Toxic: The Britney Spears Story" podcast, Alexander explained what happened. "They told me if I would sign the contracts — the annulment — they would let me and Britney continue our relationship, and if we felt the same way in six months they would give us a proper marriage," he said of his 55-hour marriage. Of course, that never happened. Alexander maintains that he and Spears have been in touch over the years, however, texting here and there. However, when he showed up at Spears' house before her 2022 wedding to Sam Asghari, he left in handcuffs. He was later convicted for trespassing. 

Britney Spears met Kevin Federline at Joseph's nightclub in Hollywood in 2004, and the two had instant chemistry. "Our eyes met and that was it. We just hit it off right away," Federline told People magazine in 2008. Getting ready to head out on tour, Spears decided to ask Federline to join her. In the early days of their romance, they grabbed a camcorder and took videos of one another. Much of that footage was used for their reality show, "Chaotic," which aired on UPN.

Knowing they had something special, Federline and Spears got engaged very quickly. First, she asked him, but he said "no" because he wanted it to be more traditional. He asked her straight away, and wedding planning began. In an attempt to thwart the media, Federline and Spears surprised their family and friends — who thought they were attending an engagement party at the then-couple's home in Studio City — with a full-blown wedding. Spears and Federline would go on to welcome two boys, Sean Preston and Jayden James, before ending their marriage in 2006. As for why things didn't go as planned, many believe Federline's partying ways caused problems in their marriage. "She tried to support him as much as she could, but at the end of the day she realized it wasn't best for her and her children. She's standing up for herself and making positive changes in her life," a source told People magazine at the time. 

Following her split from Kevin Federline, Britney Spears was rumored to have a few flings with some high-profile celebs, including Howie Day and Criss Angel, before she linked up with Adnan Ghalib. Ghalib actually worked as a paparazzo and was one of the photogs who was following Spears around during a very trying time in her life. She had just had two babies and gone through a very public divorce when Ghalib swooped in and befriended her. And everyone was skeptical about this romance. "I don't know him. I only know who he is through him following us for the last eight months. I do not think Adnan is a good person; I think he only has bad intentions," Spears' cousin Alli Sims told Us Weekly (via Access). "He has always given me a weird feeling and creeped me out. I wish he would go away," she added. But Spears kept on seeing Ghalib nevertheless. 

And while Spears and Ghalib seemed happy as they held hands all over Los Angeles, Spears' personal life was falling apart in other ways. In January 2008, she was put on a psychiatric hold, and her mental health became a serious concern. A month later, a judge appointed Spears' father, Jamie, as her conservator. Eventually, Spears ended things with Ghalib, though the exact reason isn't completely clear. The Sun reported that Spears broke things off after he purchased a pregnancy test for publicity. So, we'll just roll with that.

Britney Spears fans were convinced that she found her happily ever after when she started dating her manager, Jason Trawick. "They are totally and definitely dating. Her dad loves him. He's the best thing that happened to her," a source told People magazine in 2009. The two kept things relatively private in the early days and didn't make their red carpet debut until the 2010 Grammys. From there, the two were photographed spending time together with Spears' sons, Sean Preston and Jayden James, taking vacations, and just being so in love. In December 2011, the two got engaged. And while everyone was preparing for the third Spears wedding, things started falling apart behind the scenes.

In January 2013, both Spears and Trawick confirmed their split to People magazine in separate statements. "Jason and I have decided to call off our engagement. I'll always adore him and we will remain great friends," she said. 

"As this chapter ends for us a new one begins. I love and cherish her and her boys and we will be close forever," Trawick told the outlet. As for the reason behind the split, the two never said, though a source did tell People that infidelity wasn't involved and the former couple simply wanted "different things." 

Two months after her split from Jason Trawick, Britney Spears went public with her new guy, David Lucado. Originally from Virginia, Lucado seemed like an all-around good guy. An impressive golfer, people who knew Lucado had nothing but great things to say about him. "He is very gentlemanly like. He is very down to earth and there is never a dull moment with him. He is full of life and liked to laugh, and is a fun person to be around. He is very charismatic. There was no doubt he was going to do well in life," a friend of Lucado told E! News. And Spears wasn't shy about expressing her feelings about her new guy, either. In a since-deleted interview with ET, Spears admitted that she was in love with Lucado. 

"I like the fact that he's very stubborn and he's stuck in his ways. He's just a simple man. I adore him. He's really funny and he's really passionate. I love the fact that anything he's involved in he's passionate about, and it's contagious," she said, according to Us Weekly. But, alas, this romance didn't last very long. After about a year, the two broke things off, Spears taking to Twitter to announce that she was no longer in a relationship. "Ahhhh the single life," she wrote in August 2014.

In February 2015, Britney Spears started dating Charlie Ebersol. "I thought he was really adorable and she said he was good to people, so I went for it," Spears told People magazine of her new romance. The two really bonded, and Spears loved that Ebersol knew how to cook. Before long, she introduced him to her boys, and things seemed to be really serious. At one point, she even incorporated their relationship into her Las Vegas residency at Planet Hollywood, wearing a vest that read "I heart Charlie" on stage. After eight months of what seemed like pure bliss, Spears and Ebersol ended their relationship. As for what went wrong, well, rumor has it that Spears' dad had something to do with it.

"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 Hollywood Life after Spears' split from Ebersol was reported. "Jamie liked Charlie, but never in a million years thought his relationship with Britney would be this intense. Every man she's been with, she's wanted to marry: Adnan, Jason, David, and now Charlie. Jamie didn't break them up, though. He simply talked to Britney. He reminded her of her past and warned her what could happen if she were to marry Charlie," the source added. And so, another relationship ended in heartbreak for the pop star.

Britney Spears met Sam Asghari on the set of the music video for her single "Slumber Party" in 2016. Asghari played her love interest in the video, and the two seemed really into each other from the beginning. "I had butterflies," Asghari told Men's Health of the duo's first meeting. They eventually exchanged numbers and went out on a sushi date. Despite wanting to keep their relationship on the DL, photos of the two out on the town were soon published online. It wasn't until New Year's Day 2017, however, that Spears made her relationship Instagram official. From there, they often shared photos and videos together, which delighted many fans; Spears looked extremely happy.

After five years together, Asghari asked Spears to marry him. The "Womanizer" singer shared photos of her new diamond ring on Instagram and seemed overjoyed to be getting another chance at love. She married Asghari at her house in Thousand Oaks, California, in June 2022, and danced the night away with some super famous friends, including Madonna and Paris Hilton. And although Asghari always seemed so fiercely protective and supportive of his "lioness," he filed for divorce from her in August 2023. "After 6 years of love and commitment to each other my wife and I have decided to end our journey together," he said in a statement posted to his Instagram Stories. "We will hold onto the love and respect we have for each other and I wish her the best always. S*** happens," he added.