“Marry me”— When did The Challenge star Jordan propose to Tori on the show

Proposals on reality television have become a recurring theme, adding a mix of romance and surprise to the competitive nature of shows like The Challenge. During the November 6, 2019, episode, Jordan Wiseley proposed to Tori Deal. He asked her during an emotional moment:

“If Tori Deal would make me the happiest man in the world. Marry me.”

The memorable event was the result of months of planning, family involvement, and secrecy, culminating in one of the standout moments of the season. Jordan revealed the details of his proposal on the Challenge Mania podcast during the 2019 "War Room" bonus episode.

The proposal included a meaningful family heirloom and coordination with the show's production team.

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Jordan Wiseley's thoughtful proposal to Tori Deal on The Challenge: War of the Worlds 2

Planning the proposal

Jordan Wiseley began planning his proposal to Tori Deal about one to two months before they started filming The Challenge: War of the Worlds 2. Speaking on the Challenge Mania podcast, he said,

“I got the idea just a month or two before leaving for the show.”

Before making the proposal official, Jordan sought and received permission from Tori’s father.

“I actually talked to her dad before we left and got the okay from him that I could ask her,” Jordan explained.

The engagement ring used for the proposal was a significant family heirloom. Jordan shared,

“It was the ring that her dad asked her mom with, so it’s the original engagement ring from them.”

Tori’s mother provided the ring before Jordan left for the show, and he kept it hidden in his suitcase throughout the competition.

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The proposal

Jordan proposed immediately after winning his elimination round against Theo Campbell. The show’s production team had only 10 minutes to prepare once they realized Jordan’s intention. Jordan described the sequence of events, saying,

“After the elimination, I was getting my ring and necklace back from [the PA], and she goes, ‘Do you want the other one?’ And I was like, ‘Yeah, give it to me.’”

Theo, who witnessed Jordan’s preparation, later shared his perspective on PEOPLE TV’s Reality Check on November 7, 2019. He said,

“I knew if we went against each other and if he won, what was going to go down.”

Despite losing the elimination, Theo admitted that it was a memorable and meaningful conclusion to his time on the show.

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Tori Deal and Jordan Wiseley end engagement after more than a year

In November 2020, The Challenge stars Tori Deal and Jordan Wiseley announced the end of their engagement, more than a year after their memorable proposal on The Challenge: War of the Worlds 2. The former couple shared the news with heartfelt messages on Instagram, emphasizing mutual respect and a shared desire to focus on personal growth. Tori Deal wrote,

“Even though Jordan and I are going to be moving forward in separate ways, our love, support, and connection with one another only grows stronger and deeper.”

She assured fans that the decision was amicable and not the result of a single incident, explaining,

“The reality of some relationships is that there can be a lot of little things that slowly build up over time.”

Jordan Wiseley expressed similar sentiments, calling Tori one of his best friends.

“What this time has taught me is that I love Tori from the depths of my soul...We are just two people who love each other deeply but are both battling with our own struggles and happiness.” he wrote.

The couple, who had been together since meeting on The Challenge XXX: Dirty Thirty in 2017, emphasized that the breakup was not due to any rumors or scandal but rather a mutual understanding that they needed space to grow individually. Both requested privacy as they processed the separation and moved forward on separate paths.

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