Naked and Afraid of Love Cassalei Jackson is Kevin Federline’s stepdaughter, has a child with Zoey 101 actor Chris Massey

Naked and Afraid of Love Cassalei Jackson's mom is Shar Jackson, stepdad was Kevin Federline

If Naked and Afraid of Love star Cassalei Jackson seems familiar to viewers, that is probably because she has close ties to three rather famous celebrities. Plus, she has previously appeared on another reality series.

As Cassie reveals on Naked and Afraid of Love, her mother is actress Shar Jackson. Shar is most famous for playing Niecy Jackson, the best friend of Moesha on the popular UPN show of the same name.

Shar Jackson and Kevin Federline

Shar was engaged to Kevin Federline and they share two children together: daughter, Kori Madison Federline, and son, Kaleb Michael Jackson Federline. Cassie opens up about her mom and Kevin’s relationship on Naked and Afraid of Love and reveals that their separation affected her future relationships.

Here is what Cassie said when she first revealed the identity of her mom on the show:

My mother’s name is Shar Jackson. She was an actress. And my stepdad, Kevin Federline, left her when she was eight months pregnant. I think that that kind of ruined the fairy tale that I had dreamed of as far as relationships go. So I think that played a huge part in why my dating life has been garbage, since I was old enough to date.

As you may be aware, Kevin left Shar to be with Britney Spears. Kevin and Britney were married after three months of dating, which was just two months after Kevin and Shar’s son Kaleb was born. Shar was sucked into the whirlwind media coverage of Kevin and Britney’s relationship as the scorned pregnant fiancée. However, Shar rarely had anything but positive things to say about Kevin publicly.

From an E! Online article in March of this year:

“He’s an amazing dad,” Shar Jackson, mother of Federline’s 19-year-old daughter, Kori, and 16-year-old son, Kaleb, who was born two months before her ex married Spears, told People in January 2007, just months after he and the “Baby One More Time…” singer split up.

“He’s a great dad,” she continued, “and if you said his name right now, Kori would go crazy. That’s the love of her life.” Asked to describe the child’s bond with her father, Jackson said, “He was there for her every minute of her life until, you know, we weren’t together anymore. He did everything for her, so I guess that’s why.” (He wasn’t paying her child support, Jackson, also mom to a son and daughter with ex Corey Jackson, told Inside Edition in November 2006. But Federline was paying for school, “and they go to a very expensive private school.”)

Kevin later apologized to Shar on screen when they both appeared on VH1’s Celebrity Fit Club in 2010:

Zoey 101 actor Chris Massey arrested for domestic assault on Cassie Jackson

Cassalei Jackson and Christopher Massey

Following in her mother’s footsteps, Cassie also entered into a relationship with a celebrity that didn’t work out well at all. Cassie dated Zoey 101 actor Chris Massey and the two welcomed a daughter, Mariah, together in January of 2015. In April of 2016, Cassie and Chris made headlines after an incident between the two of them in Las Vegas resulted in Chris Massey being arrested and charged with domestic battery.

From TMZ:

The Zoey 101 star was in Vegas over the weekend and got into an argument early Sunday with reality star GF Cassalei Jackson at Marquee Club at Cosmo. Law enforcement tells us Massey allegedly pushed her to the ground.

Massey was detained by security until cops arrived. He was arrested and booked for misdemeanor domestic violence…

UPDATE –Massey’s telling friends he was indeed in an argument with Cassalei. He says when they were leaving the club she accidentally fell and security jumped to the conclusion he pushed her because they overhead their loud argument. We’re told she’s not pressing charges.

According to court records, the case was dropped by the District Attorney’s office in May of 2016.

Cassie and Chris were dragged back into the headlines again the following year when Chris requested and was granted a temporary restraining order against Cassie’s mother, Shar Jackson. It appears that Chris and Cassie were separated at the time, and Chris had recently left Mariah with Shar and Cassie for a few weeks. According to the restraining order filing, Mariah had a 4-inch “razor cut” across her forehead when Chris picked her up.

Chris claimed that Mariah told him that the cut was caused by Shar. He stated that he confronted Shar with the accusation and she responded by telling him she’d “do whatever she wants.”

Shar denied the allegations, and Chris later dropped the restraining order.

Lifetime The Mother Daughter Experiment Cassie Jackson and mom Shar Jackson

Cassalei Jackson on The Mother/Daughter Experiment

Naked and Afraid of Love is not Cassie’s first time appearing on a reality series. She appeared alongside her mother, Shar Jackson, on the Lifetime reality series The Mother/Daughter Experiment in 2016.

Here are some clips of Cassie and Shar from the show, including a fake funeral scene in which Shar visits Cassie’s grave in a cemetery:

Will Cassie finally find true love with the help of nudity and a focus on survival? To find out, be sure to watch new episodes of Naked and Afraid of Love airing Sunday nights on Discovery. Episodes are also available to stream on discovery +.

Asa Hawks is a writer and editor for Starcasm. You can contact Asa via Twitter, Facebook, or email at starcasmtips(at)

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