When the final Playboy hopeful, Lindsay, took off her shirt, Howard immediately commented her small breasts would prevent her from being in Playboy and Kevin acknowledged it was true. Lindsay responded by saying she was expecting that reaction, so she wasn't surprised by it. Lindsay went on to report she recently had sex with a girl for the first time in her life.
Lindsay told Howard the session between her and the woman took place in front of her boyfriend and began with the two of them "making out and feeling each other up" before they "went down" on each other. Lindsay mentioned that she had sex with her boyfriend right after being with the woman so she could "finish." Despite the disappointment of not making the magazine, Lindsay agreed to get on the Sybian instead, where she had an orgasm. Following her ride, Lindsay informed Howard she felt "wobbly," and Gary commented there was an exact moment when Lindsay leaned forward that he could tell she was enjoying her time on the machine.