In this first episode contestants arrived at the starting line unpaired. They had to complete a challenge prior to the start of the Race to determine the pairings. Selections were based solely on first impressions and information learned during the challenge. Jessie had the final pick, and thus was paired with Francesca by default.
• Seth → Olive—#TeamAmerica
• Matt → Redmond—#TheBoys
• Shamir → Sara—#TeamSandSexpress
• Scott → Brooke—#TeamWill&Grace
• Becca → Floyd—#TeamFun
• Vanck → Ashton—#TeamVanck&Ashton
• Tara → Joey—#TeamMom&Dad
• London → Logan—#TeamLoLo
• Jenn → Kevin—#LongHairDontCare
• Michael → Liz—#TeamLizandMike
• Jessie → Francesca—#TeamSwoleSisters
Kevin and Jenn arrived 10th at the Pit Stop. However, they failed to complete either side of the Detour before darkness made it too unsafe to continue and they were issued a two-hour penalty upon reaching the Pit Stop. Liz & Michael checked in during the penalty time, which dropped Kevin & Jenn to last place and resulted in their elimination.