Did Kailah Casillas Cheat on Her Ex with Stephen Bear from ‘The Challenge’?

Season 35 of MTV’s The Challenge kicks off on Wednesday night and based on the premiere, it’s clear that Total Madness is going to be highly competitive, and as usual, there will be lots of fights, and lots of romance. Right off the bat, U.K. competitor Stephen Bear sets his eyes on returning contestant Kailah Casillas.

It’s such an intense attraction, it almost seems as if Bear, 30, who’s competing in his third cycle of The Challenge, is more interested in winning Kailah’s heart instead of making it the Final and winning the $1 million grand prize. While Bear’s puppy love could be interpreted as cute, viewers remember how he treated Georgia during War of the Worlds and War of Worlds 2 – like trash. He’s a straight-up player.

Kailah, 26, is initially unimpressed by Bear. The former Real World/em> star who’s now competing in her fifth Challenge cycle, said that she finds his unrelenting attention obnoxious, especially because she has a boyfriend. While this should be the end of their story, due to living in such tight quarters, and the intense stress of competing on The Challenge, Kailah eventually falls right into Bear’s trap.

In the episode 2 sneak preview of Total Madness, MTV reveals Bear and Kailah making out in The Challenge lair.

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Kailah Casillas Was In A Long-Term Relationship With Boyfriend Mikey Pericoloso

While there’s always the chance that Kailah and Bear’s hook-up was a ploy for more screen time and assurance of being invited back for another season, perhaps Ex on the Beach, but their on-screen romance didn’t sit will with Mikey P. And he shared his thoughts on the matter back in November.

Mikey tweeted, “To answer a couple questions. I have no idea what’s going on. Like at all. I’m as lost as you. Kailah and I have so many amazing times together over the past 3/4 years, I would never talk bad on any of that or her. No one is trying to be on ex on the anything.”

In response, Kailah tweeted to Mikey, “Can we not make this a public spectacle? This is no one’s business but ours. You act like I haven’t contacted you at all & that is not the case. I’ve told you time and time again that we will talk when you and I are both back in Vegas. That’s the last I’ll say on that.”

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Who Is Kailah Dating Today? Does She Have A Boyfriend?

While filming of The Challenge finished back in Fall 2019, flash forward to today, and Kailah is neither with Mikey, and she’s not dating Bear. In fact, Kailah has a new man in her life, and she’s made it Instagram official with boyfriend Sam Bird.

Kailah appears to be madly in love with Bird, a former contestant on Ex on The Beach. The two went public with their relationship in January, and have been going strong ever since. Only time will tell if their relationship will hold strong once The Challenge: Total Madness finishes airing, as no one knows really knows what damning footage makes it into the final cut until the episode premieres.

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