‘The Challenge 35’: Kailah Casillas Says She Doesn’t Regret Kissing Stephen Bear While in a Relationship

During The Challenge 35: Total Madness, UK-native Stephen Bear set his sights on MTV star Kailah Casillas. Even though she initially avoided his advances and continually reminded him of her boyfriend back home, Kailah eventually gave in and kissed the known flirt. She defended her choice on Twitter by explaining she doesn’t regret it because she’s “happier than ever” now.

The Challenge 35 Kailah Casillas
Kailah Casillas | Jason Kempin

Kailah Casillas dated Mikey P for three years

Pennsylvania-native Michael “Mikey P” Pericoloso got his start in reality television on MTV series, From G’s to Gents in 2008. He also appeared in a few other reality shows, including American Ninja Warrior, and became a professional music DJ before meeting Kailah Casillas.

The Florida beauty also started on MTV as she appeared in The Real World: Go Big or Go Home in 2017 before competing in four seasons of The Challenge, where she collectively earned a little over $25,000.

It’s not clear exactly how the couple met, but they began dating around February 2017 when the couple made a public appearance at a Floyd Mayweather boxing match together.

The two then started living together in Las Vegas, Nevada, where they heavily featured each other on their respective Instagram accounts. Additionally, the couple appeared together on a May 2019 episode of MTV’s How Far is Tattoo Far.   

Kailah Casillas cheated on Mikey P while filming ‘The Challenge 35’

In October 2019, the Real World star competed on her fifth Challenge, Total Madness. During the season, UK competitor Stephen Bear aggressively pursued Kailah, but she didn’t turn him down.

While she continually reminded him that she had a man back home, he continued to flirt, and Kailah admittedly began liking his determination. On The Challenge: Total Madness Episode 5, Bear’s persistence paid off as she finally allowed him to kiss her.

In the trailer of the season, a short clip showed Kailah sitting on the UK-native’s lap and making out with him. Therefore, viewers can expect that their affair continues after their initial kiss.

Additionally, after the two finished filming, she immediately flew to Bear’s hometown and met his friends and family, seemingly without telling Mikey P anything.

After fans began questioning her boyfriend over the status of their relationship, he admitted he “had no idea what’s going on” and claimed they did not fake a break up in several tweets. She replied to him and promised they would talk once she arrived in Vegas.

Apparently, the talk ended in an official breakup because Kailah moved back to Florida and got an apartment with The Challenge 35: Total Madness co-star, Nany Gonzalez. Currently, Kailah is dating Ex on the Beach star, Sam Bird.

Kailah Casillas doesn’t regret kissing Stephen Bear on ‘The Challenge 35’

After Episode 5 aired, a user tweeted they didn’t consider Bear’s persistence as a good enough reason to cheat. The one-time finalist replied, “I never once said it’s not my fault.”

Another criticized her for “messing” with the known flirt on the show, and Kailah responded, explaining she does not “consider it a mistake whatsoever” because “everything happens for a reason.”

Additionally, she believes she currently has an “amazing” life and doesn’t think that would have happened had she not “done what I did.” After receiving a lot of flak from fans who don’t agree with her decision to cheat on her boyfriend on national television, she tweeted, “none of you will ever know all the pieces” and claims she’s “entitled to give you guys what I want to give you and nothing more.”

The MTV star closed with, “All that matters is that it happened, and now I’m happier than ever.” The Challenge 35: Total Madness airs Wednesdays at 8 p.m. EST on MTV.