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Jordan Wiseley almost said no to The Challenge: Ride or Dies : 'I was very scared' to face Tori Deal

Sydney Bucksbaum
·9-min read

There isn't much that scares Jordan Wiseley. The three-time Challenge champ is absolutely fearless in how he plays the game, which is one of the reasons why he's known as one of the best male competitors of all time. And after Russian forces invaded Ukraine earlier this year, he decided to drop everything and fly halfway around the world to spend months in a war zone to help the humanitarian efforts. Even though he had no real plan or prior experience doing anything like that, he wasn't afraid. But coming into season 38 for The Challenge: Ride or Dies, the Real World: Portland alum was absolutely freaking out.

It was going to be the first time Wiseley comes face-to-face with his ex-fiancée Tori Deal after their very public relationship ended in a very public way. The idea of not only reuniting with Deal but also having it all captured on-camera and broadcast on TV almost caused him to say no to joining this season. "But I'm excited for people to see how Tori and I were ultimately able to work through everything," Wiseley tells EW. "Everyone's seen us from before we were a thing to starting to be a thing and all the way through, it's only fitting you see this part of our story. I think that people will be surprised at how it all plays out."

Below, Wiseley dives deep on why he eventually decided to compete this season, why his "ride or die" partner is Aneesa Ferreira despite the fact that she's BFFs with Deal, and why this was the hardest Challenge for him yet.

the challenge 38
the challenge 38

mtv 'The Challenge' reveals season 38 'Ride or Dies' partner theme and cast

ENTERTAINMENT WEEKLY: What inspired you to return to the flagship after taking some seasons off and doing All Stars?

JORDAN WISELEY: They called me, and you know — Tori is a big part of my life. Those things run really deep, so going back into that environment with her was something that I was very scared of and honestly, that was a huge reason for me not going. But when I sat back for a second, I was like, "You know what? I was here first." I need to man up and deal with my stuff if I want to go play. It's real life, but at the end of the day, I wanted to play this game that I have come to love so much, and I thought it was unfair that I sat myself out.

Do you remember the moment where you realized that?

Yes. I was on a wild ride the whole first half of the year. I left the country and I went to Ukraine for around 50 days. I came back, filmed a show for nine days out in the desert. Then got a call from Georgia [Harrison] from the U.K., and she was like, "I'm going to be in Tulum. Do you want to go?" I was like, "A vacation would be awesome right now." I say yes, and on a whim I go down to Mexico and the first day I'm down there, I get the call. They're like, "This season is getting crazy right off the bat, we really want to do this thing, and we really want you to be a part of it." It was the furthest thing from my mind, honestly, but it just got put on my doorstep. I went out on the beach and did some thinking and I was like, "You know what? Let's go play."

Since this is the first time you and Tori have competed on the same season since your relationship ended, what was it like being there together?

I've got to give a lot of credit to Tori, because I at least had a heads up. I knew what I was stepping into, and she did not. She had already arrived, and was like, "He's not here. Okay." And then when I show up, I could only imagine what she was thinking. I'd prepared for it, got myself mentally ready, and knew that we were going to have to have some tough conversations — to the audience's delight, so you're welcome. [Laughs] We're all getting closure.

Since you come into the game a little later into the season, how does your entrance shake things up?

Coming in late, I was like, "How are they going to receive this?" I've been gone for a while, so I was very anxious. This is the most under-prepared I've been for a season, my butterflies were going crazy. I had zero training camp coming into it. I was like the most out of shape physically and mentally. I had just been all over the world, now I'm stepping into an emotional minefield. Anxiety was at a high. Then when I stepped in and I saw everyone's faces, and they were like blown away, it kind of humbled me a little bit. It was a cool reception, but then it also let me know that, hey, you're back and it's time to flip the switch, because even though they're excited right now, they're all going to be coming for you. And they did.

Okay but also, your "most under-prepared" for a Challenge is still miles and miles ahead of a lot of people at their best ...

[Laughs] Everyone says this! But the thing is, the fact that I can show up and know that I'm in such good shape, that's insurance for the way that I play. Not many people at all can play the way that I play. I play all out, right? I don't hold anything back. I'll let somebody know, "If you don't win, I'm coming for you," which automatically puts it on me. I'm very straight up, and that can really bite you in the butt — as we've seen. If I don't have that extra little bit to go above and beyond, and I don't have that extra swagger in me, then I'm just not as effective. So it was tough for me mentally coming in like this.

What was your reaction when you learned what this season's theme was and that you were going to be partnered with Aneesa?

When I found out it was going to be Aneesa I was like, "If there's ever a time to win and cement your legacy, it's now, with Aneesa, who is one of the most iconic players to ever do it. Get her first win ever." I think that would cement myself as one of the top guys ever in the game. So challenge accepted, pardon the pun.

But when I think "ride or die," your relationship with Aneesa doesn't exactly come to mind because of your history and how she's best friends with your ex.

There's so much that happens in our cast dynamics that the audience just doesn't see. Outside of the show, the amount that we all see each other, Aneesa and I, from the very beginning, we connected. We are Virgo siblings. There'd be times that we were riding hard for each other's teams and then there would be Dirty 30 where we were literally on opposite sides. Even when I'm at my maddest with Aneesa or my most annoyed, I will still always help her or always push her, because I want to see her do well. I love underdogs, I love the people that everyone counts out, and she gets counted out, and that feeling of when everyone's counted you out and you win, there's nothing like it. I want her to experience that as much as possible.

What can you tease about how you two work together this season?

Much like our relationship over our lifetime, it is up and down throughout the game. As you said, she's best friends with Tori, and to think that Tori and I were just going to be all Gucci the entire time would be crazy. And Aneesa can't help herself, she has to put her hands in everything. When Tori and I start to get into it, Aneesa inserts herself and that is obviously going to affect our gameplay. There's definitely a lot there, and I truly believe it was the hardest Challenge that I have ever done.

Because of the emotional drama or do you mean physically too?

The challenges were as physical as ever, and we have these studs, not only these new studs, but like Bananas, he may be 40 but the dude's getting in better and better shape each year. The Challenge is making everyone step their game up, so they're training harder and more specifically, so it's gotten a lot tougher. Physically and mentally, I really came into this not prepared on both sides. It was truly an uphill battle for myself.

How did your time on All Stars 3 affect how you played this season?

As soon as I walked into the All Stars house, it was weird — they were all like kissing the ground at my feet. I was thrown a lot of praise. I hadn't met any of these people, but they were all just talking about, "We've heard so much," and I try and block it out because you don't want to let it go to your head. You have to remember they're still coming for you, and then seeing later how hard they were coming for me despite the compliments ... it made me very aware of the reverse psychology. When I walked into this house, even though people would say this or that, I would just be like, "Dude, they're still coming for you. Don't relax. Don't ever take their flattery as they're going to let you skate through." I've seen it happen, and I just really want to be conscious of that.

How did this season compare to your previous seasons?

I did not think they were going to come for us the way that they came for us. I was like, "I've got some pretty good tenure and a good reputation. Aneesa has a ton of friends. She's the relationship queen around here. So we should be good for a while." No. There was never a week where we were good. I was like, "What the hell, man? I thought we were going to skate at least a week or two." But we do it.

The Challenge: Ride or Dies premieres Wednesday, Oct. 12 at 8 p.m. ET/PT on MTV.

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