Kailah Casillas and Stephen Bear’s hookup was the talk of this season of The Challenge: Total Madness. During the July 29 reunion episode, Kailah opened up about her decision to cheat on her longtime boyfriend, Mikey, with Bear. News of Kailah and Bear’s hookup actually leaked online while the show was filming in the fall of 2019, so Mikey got wind of the story while Kailah was still filming.
“I feel like when I found out that my ex-boyfriend knew about Bear and I…it was almost like a sense of relief in a way,” Kailah admitted during the reunion. “I wanted him to know, but I also knew that I couldn’t be the one to tell him. If I told him…it would just be in front of everyone. I didn’t want to put him through that. I’m human. I don’t know how to handle these situations. There’s no guidelines for if you f*** up on TV, here’s how you handle it.”
Kailah’s pals, Nany Gonzalez and Jenna Compono, both defended her for being unfaithful, too. “I know what it looks like,” Nany explained. “Watching that, I would feel bad for her ex-boyfriend. But there’s a lot of things that people don’t know. Things that went on behind the scenes. She did the right thing.” Jenna added, “When she [told me] what was going on, she wasn’t as upset as I thought she’d be. So that’s how I knew she wanted out of the relationship.”
However, regardless of anything else that happened with her past relationship, Kailah took full responsibility for cheating. “I don’t have anyone to blame but myself,” she said. “I’m not trying to be a victim in this whatsoever. It was just a hard situation to deal with and I didn’t know what to do.”
After Kailah was eliminated from The Challenge, she spent two weeks in the U.K. with Bear. Then, she returned home to the States to move out of the home she was living in with Mikey. For the last several months, she’s been in a relationship with Love Island star, Sam Robert Bird.