If competition is the main goal of The Challenge, hooking up may be the secondary objective. We’ve seen some epic romances begin on the show, but we’ve had our share of uncomfortable Challenge pairings.
This list is made up of relationships that seemed like they were meant to be romantic, but they were pretty much devoid of any real romance. To be on this list, the relationship can’t just be a one-time hook up and it needs to stretch over more than one episode.
Nany & Will (Vets & New Threats)

Nany would be the first person to admit that her fling with Will was never meant to turn into a long-term relationship. She’d just broken up with Kaycee and Will was getting over his jealous outburst from watching Dee and Bananas hook up. So when these two first hooked up, it seemed like it was going to be a fun and lighthearted romance. Then, Will lost his cool when cheaters caused the Broken Dreams challenge to be discarded and Nany sided with the veterans. While she tried to reach out to Will, it was clear Nany wasn’t going to make compromises to keep Will happy. More recently, she made it clear that the relationship only got worse after the season ended.
Michele & Callum (Battle for a New Champion)

This is a one-sided relationship because Michele seemed fully invested. Callum seemed interested as well, but not interested enough to end his relationship with the girl he was dating at home. Michele was upset when Callum got eliminated, but by the time the reunion rolled around, Michele realized she was being played and Callum failed to make either of his relationships stick.
Dee & Rogan (War of the Worlds 2 + Total Madness)

It’s hard to know why Rogan and Dee first gravitated toward each other. Maybe it was because Dee innately lusts for strippers, maybe Rogan was looking for a hook up, or maybe Dee was looking for some type of safety. Throughout the season, it seemed like Rogan was annoyed by Dee (like when he had to be paired with her in the swimming challenge), but he never had the guts to send her into an elimination. They won the season together, and some sexual chemistry spilled into Total Madness. On that season, Rogan was also involved in a plot to get Dee out of the game, and any semblance of trust was thrown away to send Dee into an elimination against Mattie… which Dee won.
Nany & Hunter (War of the Worlds)

Throughout the second half of War of the Worlds, we saw Nany and Hunter getting cozy (even though Hunter spent the first half of the season with Julia in his bed). While the two enjoyed each other’s company, it wasn’t enough to keep Hunter grounded and prevent him from causing chaos in the house. This coupling didn’t seem too bad during the season, but at the reunion, it was revealed Nany tried to reach out to Hunter but he ignored her because he had gotten a girl pregnant.
Bananas & Natalie (Vendettas)

If there was ever a scam relationship that the Challenge assembled for publicity, it was this one. As soon as Natalie Negrotti entered the Challenge house as the first girl representing Big Brother, Bananas took an interest in her. They seemed to get cozy fairly quickly, but the relationship was strained when it was revealed Bananas kissed Kayleigh early into the season. After Vendettas, the “couple” was “spotted” on a date together, and during Final Reckoning Kayleigh openly called the relationship a publicity stunt.
Melissa & Nicole (Vendettas)

Melissa came into the Challenge like a firecracker, and the Ex on the Beach UK star was never shy about hooking up. This time, she decided to respond to Nicole’s advances, and the two quickly started some type of a showmance. Nicole was rebounding from Laurel (for the first time), and Melissa decided to take the bait — probably for strategic reasons. It didn’t help Melissa get too far in the game, and the two girls never rekindled a romance after this season, but it did get them cast on All Stars: Rivals.
Ashley & Jamie (Rivals 3)

On the first night, in the middle of the Are You the One? kids fighting, Ashley and Jamie randomly hooked up. This almost seemed like an attempt to get camera time, but it was clear that this wasn’t just a one night stand when Ashley yelled at Nicole in a club because she wrongfully believed Nicole and Jamie had some type of romantic relationship. Ashley seemed invested in Jamie, and he insisted he thought she was a great girl… but a few nights later Ashley woke up and Tony was in her bed.
Jay & Jonna (Battle of the Exes 2)

The stand-out romance from Battle of the Exes 2 is obviously Zach and Jenna, but as their relationship started to blossom, their partners navigated the uncomfortable transition by trying to couple up. Jay and Jonna had a few make out sessions and some awkward conversations, but their fling went nowhere substantial. Clearly, there was no chemistry there, but there’s also no bad blood with this attempted hook up.
Dunbar & Paula (The Island + more)

Most Challenge viewers know Dunbar and Paula are exes, mostly because they were on Battle of the Exes together, but can anyone remember any of the good times they had together? The two hooked up on The Island, but it felt like Dunbar was begrudgingly forced into a partnership with Paula on The Duel 2 (which may have involved some hooking up). They also worked together on Cutthroat, though Paula just got mad when Dunbar entertained the idea of voting her into the Gulag (though there may have been some more hooking up). It only felt like these two had any unity when they were partnered on Battle of the Exes and they were actually exes.
Brooke & Evelyn (The Gauntlet 3)

By her own admission, Brooke showed up on the Gauntlet 3 and just decided she was done with men. This was an unexpected opportunity for Evelyn, and she was excited to pursue her crush on Brooke. The two girls coupled up during the Gauntlet 3, but once Brooke left, it was clear her heart wasn’t in this relationship. Coral claimed that she didn’t think Brooke was even a “real” lesbian, and that may be true, but we can’t forget that exploration is a part of forming an LGBTQ+ identity.
