Before the Challenge Dirty 30 premiered, I put out an article linking every person’s career hookups. It got over 11,000 clicks, so I decide to write up the Challenge Hook Up Hall of Fame, because you guys love to know about who is fucking. Sex sells.
Challenge Dirty 30: Who everyone’s hooked up with
With Challenge season 30 coming around the corner, I’ve decided that we should air out some dirty laundry for the…
This could have later installments. Let’s get straight on a top. We will not be ranking them, but these are the top 9. The elite of hooking up. We are also trying to avoid recency bias (so no Cory or Tony). I am avoid Real World hookups, which is a main reason why Zach, Nany, and others did not make the list.
The difference between Paula and others is that she has had interesting and diverse tastes. Paula’s total quantity is strong. What Paula has over people is that she went on these Challenges with the intent on having fun, maybe hooking up with cute guys, and she wasn’t super focused on winning till after 5 Challenges. When she picked her Fresh Meat 2 partner, she asked if he had a boyfriend…That’s what we are working with.
Paula is also famous for her hot tube make out sessions with whatever hot girl is around. She’s put her tongue down the throat of both Emily and Laurel, and many other hot females. She’s had weird relationships, like Mike and Ty, and tragic ones like with Dunbar (her Dummy Bear).
If you’re able to pull-out a three-way with two of the hottest girls in Challenge history (Rachel and Veronica) on your first Challenge, then you automatically go in. Then you throw in Coral, one of the most intimidatingly beautiful people in Challenge history. The main centerpiece is his long term relationship with Cara Maria Sorbello. A girl known for being one with her sexuality. And according to her, Abram is the best she’s ever had by far.
When talking about numbers, Tonya is the Wilt Chamberlain of hookups. Any modern player looking at Tonya’s hookup numbers would have a permanently dropped jaw. Having sex with Tonya was somewhat a rite of passage for elite male competitors. Landon, Derrick K, Kenny, Mark, and Theo had a time with Tonya. Even more amazing is when Tonya got married, then called her husband if it was okay for her to have sex with Davis Mallory on the Inferno 3. Note: Davis is Gay.
The JEK group likes to call Wes ugly. If Wes’s ugly, I want some of that, because he has a stacked line-up of hookups. He seriously dated Johanna for a couple years, and had a nine month relationship with KellyAnne. Both those girls are considered by some to the best hottest in RW/Challenge history, and he had them lock-down for a few years of his life. Wes also had a hookup with a young Theresa on Fresh Meat 2. Theresa frequents many top 20 and top 10 lists. Add in a Mandi Moyer hookup from Rivals 1, where they possibly dated for a while — Wes is one girl away from the great five woman line-up ever. Hell, he might already have the best five woman line-up with four girls.
A former cheerleader, Jenn brought her A game when it came to hookups. Yes, there was the ill-fated hookup/showmance with Adam King on Rivals 1 that she regrets. Besides that she has had some Prime Rib with Darrell and Derrick. Being able to bag some power players like that is like going to Stanford for Undergrad and Harvard for Post-Grad.
My favorite hookup and relationship of hers was with Pete Connolly from Fresh Meat 2. That guy was tall, handsome, and had a great smile. They both made the final. Second favorite hookup is her time with Rachel Robinson on the Island and Duel 2.
Queen V has also put up some great numbers in her career.
She’s been with men and women alike, younger and older. Even near 40, guys still dream of hooking up with the Queen.
In Evan’s first two Challenges he hooked up with Robin, Jodi, and Coral. Three beautiful girls, one whose done some nude modelling, an athletic freak, and Coral (who is scary in the best way). On the Ruins, he was known for having a possible hookup with Veronica as she wanted to be aligned with the power player of the house. There’s a heavily rumored hookup with Rachel Robinson on the Duel 2.
Evan dated Emilee Fitzpatrick from RW Cancun for a while. Wasn’t a great competitor, but Emilee is hot. May have also dated Paula. For a person who did 6 Challenges, Evan has great numbers. Super efficient.
If Tonya is Wilt Chamberlain, Robin is the Kareem Abdul-Jabbar of the Challenge when it comes to hookups. Robin’s consistency and power when it came to putting up raw numbers was strong. Her relationship with Mark Long from Battle of the Sexes 2 is one of the famous throwback Challenge relationships that got brought back together for the first Battle of the Exes. A relationship that had started over 10 seasons before!
She also hooked up with Kenny, Evan, and Derrick, that’s an entire alliance. During the Island, she had her drunken relationship with Dan Walsh. The only thing that slowed her down was a baby.
Chris Tamburello (CT)
How can you do this list without CT? He has the most famous relationship in Challenge history. He and Diem were on and off for a decade, had their main run from the Duel 1 to Gauntlet 3. They had flings on Rivals 2 and Exes 1 as well.
CT’s dove into some other ponds before. During both same sex Rivals seasons, CT was a dog. He started each of those by going for surprise picks (basically the girls that were down for him from day one). CT had sex with Anastasia in the jungles of Thailand on Rivals 2, had Mandi clinging on him early on Rivals 1, made a bad decision with Shauvon on the Duel 2, and caught the Laurel bug late in Rivals 1. There are rumored hookups with Cooke and Nany, and my favorite denied rumor is that he hooked up with Shane. It’s not true, but you wish it was.