Episode two begins in the early morning at the coupled girls' resort, Tango Mar. As Nikkole gets out of bed she asserts that she is prepared to live through this experience for what it is without any fear or regrets.

Later that morning the couples meet Mark at poolside, Tambor Tropical for their first date selection. The couples choose their dates by randomly picking shells that contain the names of the singles. John goes first and is paired with Anna Maria, the party promoter from San Diego. Tony picks Donna, an entrepreneur from Dallas, Pennsylvania. Genevieve says in an interview that she is not concerned at all, because she knows that Donna is not someone Tony would be attracted to. Edmundo selects Hilary, a graduate student. Catherine has to take a deep breath after watching Hilary and Edmundo warmly greet one another. Tommy picks Kristen S., a pediatric nurse from San Diego.

Shannon picks Kaine, a law student. In the moment before Kaine was selected, John chants and roots for Ros