Why Did Kevin Federline and Shar Jackson Break Up?

Kevin Federline and Britney Spears’ whirlwind romance began in the glare of 2000s tabloid culture and ended just as dramatically. When they met in 2004, Federline was still dating actress Shar Jackson, who was pregnant with their second child at the time. Despite the public backlash, Spears and Federline married that same year after a brief engagement. They later welcomed two sons together, Sean Preston and Jayden James. So, what really happened between Jackson and Federline that led to their split? Here’s what to know.

What happened between Kevin Federline and Shar Jackson that led to their breakup?

Kevin Federline and Shar Jackson were together for several years in the early 2000s, a period that preceded Federline’s high-profile relationship with Britney Spears. The couple met in the late ’90s and became engaged, welcoming their first child, Kori Madison, in 2002, followed by their son, Kaleb Michael Jackson, in 2004. Their relationship faced challenges, particularly as Federline’s attention shifted toward Spears. They ultimately split in 2004, shortly before he began dating Spears.

So, what ultimately led to Federline and Jackson’s breakup? In Federline’s new memoir, You Thought You Knew, he explains how he cheated on Jackson. According to Us Weekly, Federline wrote about how he regrets cheating, as he lied to Jackson and told her he “booked a commercial shooting overseas” when he really planned to join Spears in Europe for her “Onyx Hotel Tour.” He later called Jackson to tell her the truth. Federline admitted he was falling for Spears and had been pursuing a relationship with her.

“I knew [the truth] would hurt her, and I didn’t want that,” Federline wrote. “If I could go back in time, I’d handle that whole thing differently. But life doesn’t work like that. We f*** up and we learn.”

Federline told Jackson that he intended to stay in their children’s lives. And he also wrote about how he was “unhappy” in his relationship with Jackson, which he wished he had told her before he cheated.

“I wasn’t the man I needed to be,” Federline wrote. “I wasn’t the man I wanted to be. And for that, I am truly sorry.”

Shar Jackson previously spoke about wanting to stay friends with her ex-fiancé

Kevin Federline broke Shar Jackson’s heart when he left her for Britney Spears. However, the co-parents remained friendly through the years. In 2007, Jackson spoke to People about her relationship with Federline.

“Obviously, the relationship didn’t work out for a reason, and we’re cool with that,” she explained. “But we’re still a part of each other’s lives. And our children get to see two people who aren’t together but still have a great relationship, and I think that’s really important.”

Jackson also mentioned that she wanted to keep her and Federline’s kids in close proximity to Federline and Spears’ kids, who were just 14 months old and 2 at the time.

“We definitely make sure the kids all bond together,” she said. “I mean, they’re siblings, they need each other.”

Britney Spears says she didn’t know that Kevin Federline had a baby on the way

Britney Spears wrote about her romance with Kevin Federline in her memoir, The Woman in Me. According to Page Six, she wrote about how she had “no idea” that Shar Jackson was pregnant when she met him. She also didn’t know about his and Jackson’s older child.

“Kevin had a ‘bad boy’ image. Still, I had no idea when we met that he had a toddler, nor that his ex-girlfriend was eight months pregnant with his second baby,” she wrote.

“I was clueless,” Spears continued. “I was living in a bubble, and I didn’t have a lot of good, close friends to confide in and get advice from. I had no idea until after we’d been together for a while and someone told me, ‘You know he has a new baby, right?'”