Bartender Cottrell (21) has dates with Avise 20 Charlotte 21 Shannon 20 Jessica 22 Anna 18 Cottrell's nostalgia date starts with a visit to a vintage clothing store followed by some breakdancing lessons In the second segment 19 year old Riana states she's a Steelers fan. Her dates are with Steve 22 Bobby 22 Josh 24 Alex 22 Fin 23 Riana's date starts with a melted chocolate fantasy followed by some carnival contests and a stop for cotton candy.