Cindy Margolis stopped by to promote the July issue of Playboy and stunned the crew with her outfit. Howard was charmed: "Jesus Christ you look good. I'd take a date with you." Cindy laughed that she'd really brought "the girls" out today, and Howard thanked her. Cindy then confessed she was on a streak: after recently breaking up with her husband of ten years, she was now trying to live the reckless twenties she missed while married.
Cindy told the crew about her favored mouth-and-two-finger oral sex technique (to be use on a woman), but Howard didn't think he was coordinated enough to pull it off. Cindy replied that she actually preferred to teach men – and even women - the technique. Cindy laughed that she recently ended up in a threesome during one of these "teaching" sessions. Howard then brought in the three contestants who'd won the chance to compete for a date with Cindy.