Britney Spears’ Relationship History Is Full Of Surprises

Ever since "Framing Britney Spears" (the sixth episode of The New York Times Presents series detailing the #FreeBritney movement) premiered on Feb. 5, the pop star’s love life life has been thrust back into the spotlight. For the past four years, she’s been boo’d up with Iranian model and personal trainer Sam Asghari, but leading up to her current romance, Britney Spears’ relationship history is more than a little complicated. Over the years, she’s been married twice and engaged three times, and with Asghari, it seems she’s finally found her person.

While her first serious relationship with her high school sweetheart, Reg Jones, was kept relatively private, her next relationship with Justin Timberlake was anything but. The two Mickey Mouse Club alums had an epic romance with a messy end, which was explored in depth in "Framing Britney Spears." From there, Spears dated a series of dancers, actors, choreographers, and producers until she met Asghari in 2016.

"What I love the most about my relationship is the fact that it’s so normal," Asghari told Entertainment Tonight back in September 2019, and TBH, I couldn’t agree more. Here’s everything I know about Spears’ love life before she crossed paths with her current boo.

Justin Timberlake, 1999-2002

Justin Timberlake first met Spears back in 1992 on the set of The Mickey Mouse Club, but it wasn’t until seven years later that the two started up a romance. "He’s everything," Spears gushed about Timberlake to The Observer in September 2001, adding, "It is a deeper love now than when I was younger. Like, we’ve gone through so much together and we’ve known each other since we were 12 years old. We know each other inside and out."

After just about three years together, the couple split in March 2002, and things quickly got ugly. The "Framing Britney Spears" documentary revisited Timberlake’s subsequent press tour, where he talked about being cheated on by his ex. Soon after the doc was released, Timberlake issued an apology to Spears for his actions 18 years earlier. Luckily, a source for Us Weekly reportedly claimed Spears "has no hard feelings" toward her ex.

Wade Robson, 2002

It’s still unclear when or if Spears and choreographer Wade Robson actually dated, but the two allegedly had an affair while Spears was still dating Timberlake. "Justin Timberlake uncovered Spears’ alleged affair with Wade Robson when he discovered a note in Spears’ room in February 2002, on the night that the two pop stars were scheduled to appear on Saturday Night Live," Rolling Stone reported in March 2010.

Timberlake’s 2002 song, "Cry Me a River," is rumored to be a response to the reported affair, though Spears never commented on the Robson dating rumors herself.

Colin Farrell, 2003

In January 2003, Spears hit the red carpet with actor Colin Farrell for the premiere of his movie The Recruit. At the time, Farrell insisted they weren’t dating. "She’s just a mate," he told Entertainment Tonight. "Seriously, we just met a week ago, [we’re] having a laugh."

Apparently, the two ended up sharing a smooch that night, but little else came of the relationship. "Yes, I kissed him," Spears told W in July 2003. "Of course I did. He’s the cutest, hottest thing in the world — wooh! He’s such a bad boy. But it was nothing serious."

Columbus Short, 2003

Former backup dancer and actor Columbus Short reportedly had a fling with Spear while he was still married to his first wife, Brandi Short. "It’s true I slept with Britney, [but] we never had sex because another person was in the room at the time," Short told The Star in February 2004. "We shared a bed and were really close, kissing and hugging. The chemistry was magical … Our feelings were so strong."

The incident reportedly led to the end of Short’s marriage, though Spears has never commented on her reported romance with Short.

Jason Alexander, 2004

On New Year’s in 2004, Spears and her childhood friend Jason Alexander spontaneously decided to get hitched at a Las Vegas wedding chapel. 55 hours later, the marriage was annulled. "She just came out and asked me," Alexander later said of the night during a February 2012 interview with ABC News. "She was like, ‘Well, let’s get married.’ And I was like, ‘Sure. You know, let’s do this’ … I went with my feelings. I was in love with her."

During her own interview with E! News in March 2004, Spears said the wedding had been a rash decision. "It was me being silly, being rebellious, and not really taking the responsibility of what I was doing, you know?" she said. "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."

Kevin Federline, 2004-2007

After ending her brief marriage with Alexander, Spears met backup dancer Kevin Federline at a club in Hollywood. "Our eyes met and that was it. We just hit it off right away," Federline told People years later in December 2008. "I was madly in love with her. Everything just seemed so right." Three months after meeting, the couple tied the knot in September 2004 in a surprise wedding. "…I was like, ‘What are we waiting for? We know this is the real thing, why not just do it now?’" Spears explained to People soon after. "That’s why I wanted to sneak and do it our little way."

Spears and Federline welcomed their first son, Sean Preston, a few days before their one-year wedding anniversary, and a year later, they welcomed their second son, Jayden James. Fans were then shocked when Spears filed for divorce in November 2006, just two months after her younger’s son birth. By July 2007, the divorce was finalized, with the two agreeing to share custody of their sons.

"I think I married for the wrong reasons," Spears explained in her 2008 documentary, For the Record. "Instead of following my heart and doing something that made me really happy, I just did it for the idea of everything."

Jonathan "J.R." Rotem, 2006

Record producer Jonathan "J.R." Rotem reportedly had a brief fling with Spears in late 2006, and during a April 2007 interview with Complex, Rotem bragged about their reported sexual exploits. "We’re working together still, but I’m not sure if I want to be tied down, period," he added. Spears never commented on the rumored romance.

Adnan Ghalib, 2007-2008

Spears surprised fans when she stepped out with tabloid photographer Adnan Ghalib in late 2007, but according to Ghalib, their relationship was the real deal, and during an April 2018 interview with The Sun, he looked back on his time with her fondly. "People don’t know, but she has a goofy side and is great fun to be around. She has an epic sense of humor and likes joking about other celebrities," he said. "She is also such a generous person with a huge heart." The two reportedly went their separate ways in early 2008 after a few months of dating.

Jason Trawick, 2009-2013

After months of dating rumors, a source for People confirmed Spears was romancing her agent, Jason Trawick, in June 2009. "They’re very sweet together," the source reportedly claimed, adding that Spears "always had a crush" on Trawick. "He makes Britney really happy, and he’s great with the boys." After two years together, Spears hinted that she saw marriage in their future. "We have such a great time together! He makes me laugh, and we are so comfortable being ourselves," she told Us Weekly in April 2011. "Maybe [I’ll marry again]. Never say never!"

In December 2011, Trawick popped the question on his 40th birthday, and Spears teased the news on Twitter. "OMG. Last night Jason surprised me with the one gift I’ve been waiting for," she wrote. "Can’t wait to show you! SO SO SO excited!!!!" Unfortunately, the couple decided to go their separate ways a little over a year later. "Jason and I have decided to call off our engagement," Spears said in a January 2013 statement for People. "I’ll always adore him and we will remain great friends."

David Lucado, 2013-2014

A month after calling her engagement with Trawick, Spears first sparked dating rumors with bartender David Lucado after she and Lucado were reportedly spotted on a Valentine’s Day date, per E! News. Soon after, a source for E! News reportedly claimed the two were "definitely dating." By November 2013, Spears told Entertainment Tonight she was "in love" with her new beau. "He’s just a simple man. I adore him," she said. "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."

Unfortunately, things took a turn in August 2014. After 18 months of dating, the two reportedly split after rumors surfaced about a video that reportedly showed Lucado kissing another woman. Spears seemingly confirmed breakup rumors when she tweeted, "Ahhhh the single life!" and soon after, a rep for the singer confirmed she was single to People.

Charlie Ebersol, 2014-2015

In November 2014, a source for Us Weekly reportedly claimed Spears was dating writer and producer Charlie Ebersol and had already been together for a few weeks. "He’s a sweet guy, and we’ll see where it goes," the source reportedly claimed. Soon after going public, Ebersol gushed about Spears in a December 2014 interview with People, saying the pop star has an "enormous heart." During her own interview with People, Spears explained how she was introduced to Ebersol through her assistant. "I thought he was really adorable and she said he was good to people, so I went for it," she said.

The two went on to date for eight months and even attended the 2015 Billboard Music Awards together before they reportedly went their separate ways in June 2015. "I just felt that he was in it for the wrong reasons," a source for Us Weekly reportedly claimed at the time. Neither Spears nor Ebersol ever commented on their split.

Sam Asghari, 2016-2021

Spears first met Sam Asghari in October 2016 on the set of her music video for "Slumber Party." According to Spears, the two hit it off over their shared love of sushi and decided to exchange numbers. "…I found his number in my bag. I was like, ‘He is really cute. This guy is really cute,’" Spears explained during a January 2017 appearance on CBS Radio’s Fast in the Morning With Nathan Fast. "So then I called him, and ever since then, he is just a really fun, funny person."

Over four years later, the couple is still going strong, and following the February 2021 release of "Framing Britney Spears," Asghari opened up about his future with Spears during an interview with People. "I have always wanted nothing but the best for my better half, and will continue to support her following her dreams and creating the future she wants and deserves," he said. "I am thankful for all of the love and support she is receiving from her fans all over the world, and I am looking forward to a normal, amazing future together." Aww.

Here’s hoping Spears and Asghari have a long, happy future ahead of them.

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