100 Days Wild (2020)

S11E1 Welcome to Chicago

The group is off to Chicago, featuring Aneesa, Cara, Chris, Keri, Kyle, Theo, and Tonya, and we get to join them on this adventure. We first meet Theo and Tonya, where initial tension arises due to Tonya's limited exposure to diversity, especially with Theo being a black man. However, they quickly navigate through this discomfort and reach the striking orange door of their new place. Next to arrive is Aneesa, who instantly captivates Theo with her lively spirit and carefree nature—she’s known to stroll around in the buff. But when Aneesa reveals she’s a lesbian, Theo is taken aback. Nonetheless, he brushes it off, convinced that over their four-month stay, anything could happen.