시즌 1, 에피소드 4: Things are getting serious for The Cougar. Host Vivica A. Fox gathers the guys and challenges them to anonymously reveal their deepest, darkest secret to Stacey. Stacey chooses one man who admitted he cheated on an ex-girlfriend and one man who spent time in drug rehab. The two men go on a skydiving date with her, but only one of them returns from it as Stacey sends one brokenhearted guy packing. For the next challenge, Stacey asks the guys to perform an original song that communicates how they feel about her. Stacey takes the winner to a theater where the couple connects over a romantic dinner and a surprise live concert. The couple returns home, only to be shocked to find one of the other guys in tears at the prospect of elimination. More guys are sent home during an emotional elimination ceremony. The men who remain in the house each have a strong connection with the Cougar and an even stronger desire to win her heart.