"Messy" Fessy Is Back on 'The Challenge' to Stir up Romantic Drama

Faysal Shawn “Fessy” Shafaat’s relationship history is causing some drama on ‘The Challenge: USA.’ He’s dated and hooked up with three women!

Jamie Lerner - Author

Aug. 14 2023, Published 9:48 a.m. ET

Fessy in 'The Challenge'
Source: MTV

Spoiler alert: This article contains minor spoilers for The Challenge: USA Season 2, Episode 2.

Now that The Challenge: USA Season 2 is officially underway, the drama has begun. Naturally, no one attracts more drama than Faysal Shawn “Fessy” Shafaat, a Big Brother turned MTV’s The Challenge alum. Having been on several reality shows, Fessy has dated and hooked up with his fair share of women, so it’s no surprise that multiple women he’s hooked up with are on The Challenge: USA Season 2.

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While Season 1 of the CBS spin-off series only had contestants from CBS shows, Season 2 dives much deeper into the MTV series’ lore. With six iconic vets of The Challenge, along with Survivor and Big Brother players who have also competed on the MTV version of the show, interpersonal drama is sure to be front and center. So what’s going on with Fessy’s relationship history? Did he hook up with three different women competing this season?

(L-R): Amanda, Michele, and Tori in 'The Challenge: USA'
Source: CBS

(L-R): Amanda, Michele, and Tori in 'The Challenge: USA'

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Fessy’s relationship history is creating drama in ‘The Challenge: USA’ Season 2 house.

Like in Big Brother, contestants of The Challenge are forced to live and interact with one another. So even though interpersonal relationships have less of an effect on the outcome of the game than in BB or Survivor, they are still majorly at play. Add in the fact that several competitors have already been on reality shows together, and we have a recipe for chaos.

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In Episode 1, we learn that Fessy hooked up with Tori Deal, Amanda Garcia, and Michele Fitzgerald, which created a wedge in the relationship between the three powerhouse women. By Episode 2, we’re already seeing the effects of that drama come to fruition. So what is Fessy’s relationship history with them?

Fessy first hooked up with Amanda on ‘The Challenge: Spies, Lies, & Allies.’

Season 37 of MTV’s The Challenge: Spies, Lies, & Allies is where all the drama begins. Fessy and Amanda immediately hit it off and form a bond. Although Amanda is eliminated relatively early, it’s clear that she and Fessy have a connection that could lead to a romance outside of the house. Even still, after she’s eliminated, Fessy and Michele Fitzgerald also get pretty close.

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Fessy and Amanda on 'The Challenge: Spies, Lies, & Allies'
Source: MTV

Regardless, after the season ends, Fessy and Amanda make their relationship as “official” as one would expect a reality television couple to get. While on a trip to Mexico in Sept. 2021, they share photos and videos together to go public. But their solid relationship was short-lived. Although Fessy said on camera, “I don’t wanna be a player no more,” a viral video of him getting handsy with a fan led to the end of his and Amanda’s relationship.

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Fessy also hooked up with Michele in the midst of his relationship with Amanda.

As seen in several of The Challenge: Spies, Lies, & Allies reunions, Michele and Fessy also hooked up at some point. Amanda calls her out for it during the official reunion when Michele expresses her sorrow over Emmanuel and Tori’s relationship. “It doesn’t upset me that they’re together,” Michele said. “But, he just was my person … I was mad at Emanuel, but I was mad at Tori. And I really, really had a grudge against her.”

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But then, Amanda points out that Michele is being a bit hypocritical. “She’s mad at Tori for going for Emanuel, but she went for Fessy as soon as Fessy got off the show,” Amanda said. “So, it’s like, I was your friend, b--ch, and you went straight on to his d--k. You’re fake as f--k.” Basically, Amanda learned through rumors that Michele and Fessy hooked up after filming the show, but both Fessy and Michele say that it was just a friendly thing.

Tori also hooked up with Fessy a year later.

Fessy loves The Challenge, so naturally, he returned for Season 38 even though he was disqualified from Season 37 for a physical altercation between him and Josh Martinez (who is also on The Challenge: USA Season 2). But more than The Challenge, Fessy loves women. In Season 38, he hooked up with Tori Deal, who had only split from fiancé and fellow competitor Jordan Wisely only two months earlier.

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Jordan Wisely and Tori Deal on 'The Challenge'
Source: MTV

“It was the worst decision of my life,” Tori told Us Weekly of hooking up with Fessy. “I mean, it’s, no offense to Fessy, like, you know, he’s a good person and … I was in a really bad spot. Like, I was just living in the s--t of my life.” This was in 2022, a full year after his split from Amanda, so the Fessy drama is likely done, right?

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Nope! Not when Fessy is now on a season with all three of his past flings. His past relationships with Big Brother alum Haleigh Broucher, The Challenge competitor Gabby Allen, and Wynn Bet on-air host Claudia Bellofatto only add to messy Fessy’s lore. Will he be able to stay out of trouble this season? With Sebastian and Tori’s romantic connection looming over the house, it’s possible that Fessy could find himself at odds with even more challengers.

New episodes of The Challenge: USA air every Thursday and Sunday at 9 p.m. EST on CBS.

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