Here's a Complete Breakdown of Britney Spears’ Romantic Involvement Over the Years

Britney Spears recounts her celebrity relationships in The Woman in Me

Britney Spears' new book, The Woman in Me, delves even further into the pop culture icon's most infamous relationships. Spears went on to have many high-profile engagements and marriages, including a 55-hour marriage to Jason Alexander in 2004 and a subsequent announcement of her engagement to backup dancer Kevin Federline that same year. In February 2008, Spears was put under conservatorship after her breakup with Federline and other personal problems. Read on to learn more about all of the singer's past relationships.

1. Spears had a boyfriend named Reg Jones when she was 14 

In her upcoming memoir, the singer reveals that she had an affair with her older brother Bryan Spears' closest friend when she was 14 and he was a senior in high school. Spears, now 41, does not reveal the identity of her high school sweetheart in her much-anticipated book, although she was involved with a guy called Donald "Reg" Jones at the time. As per Page Six, she lost her virginity to Jones when she was a teenager, and back in 2021, he also told the New York Post, "She was the love of my life." However, he clarified, "I don’t go around wishing we were back together... I wish her the best in all that she does." 

2. The 'picture-perfect' Hollywood romance with Justin Timberlake 

When Justin Timberlake and Britney Spears broke up in 2002 after four years of dating, it wasn't exactly on a happy note. After their breakup, Timberlake insinuated adultery on Britney's part with his song Cry Me a River, the aftermath of which is covered in Spears' memoir. Besides, compared to his carefree Hollywood persona at the time, Spears talks of experiencing mental turmoil after the split. The memoir also details that Timberlake pushed for an abortion when Spears was pregnant with their child and Spears' unease with Timberlake openly talking about their sex life. After his revealing 2003 interview with Diane Sawyer was shown in the documentary Framing Britney Spears in 2021, Timberlake issued a public apology to Spears. On Instagram, he wrote, "I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn or did not speak up for what was right. I specifically want to apologize to Britney Spears and Janet Jackson both individually because I care for and respect these women, and I know I failed."

3. A two-week fling with Irish actor Colin Farrell

In her memoir, Spears stated she met Farrell on the set of the 2003 action thriller S.W.A.T. Apparently, Spears and Farrell got into 'a two-week brawl.' She further added, "Brawl is the only word for it — we were all over each other, grappling so passionately it was like we were in a street fight." Eventually, Spears even accompanied him to the premiere of his film, The Recruit, in January 2003. Spears says in her book she did her best to keep from being 'too attached' to Farrell. As per excerpts obtained by Time, she said, "As I had before when I’d felt too attached to a man, I tried to convince myself in every way that it was not a big deal, that we were just having fun, that in this case, I was vulnerable because I wasn’t over Justin yet."

4. A 55-hour marriage to Jason Alexander

Spears also spoke about the beginning and end of her marriage to Alexander on a 2004 New Year's trip to Las Vegas. She says that she and Alexander spent the night together after partying for many days with a group of pals that included Paris Hilton. As Time reported, she said, "He and I got sh-t faced. I don't even remember that night at all, but from what I've pieced together, he and I lounged around the hotel room and stayed up late watching movies—Mona Lisa Smile and The Texas Chainsaw Massacre—then had the brilliant idea of going to A Little White Chapel at three thirty in the morning. People have asked me if I loved him. To be clear: he and I were not in love. I was just honestly very drunk — and probably, in a more general sense at that time in my life, very bored."

5. Spears' Love at First Sight: Kevin Federline

The whirlwind affair between Spears and the backup dancer started in 2004 while Federline was performing with Justin Timberlake. Federline told People in 2008, "I met her at a club in Hollywood, Joseph’s. Our eyes met and that was it. We just hit it off right away. I learned real fast how much of a whirlwind the press and everything was." They got married in a secret ceremony in Studio City, California, in September 2004, after just three months of dating. A few weeks before their first wedding anniversary, the couple had a son, Sean Preston, and in 2006, they welcomed son Jayden James. By the end of November 2006, Spears had filed for divorce from Federline, alleging 'irreconcilable differences.' The divorce decree between the two was finalized in July 2007, and as part of that agreement, they share legal and physical custody of their two children.

6. Spears' third marriage to Sam Asghari

Asghari seemed to be Spears' rock during the conservatorship struggle, which ended in November 2021, as she tried to have her father, Jamie Spears, give up control of her multimillion-dollar inheritance. Asghari appeared in Spears' Slumber Party music video in 2016, and the two started dating five months later. After being with Asghari for six years, Spears said that she was 'a little shocked' by the breakup. As reported by BBC, she said, "I've been playing it strong for way too long, and my Instagram may seem perfect, but it's far from reality, and I think we all know that. I would love to show my emotions and tears on how I really feel, but for some reason, I've always had to hide my weaknesses."