Living Single - Season 4 Episode 10 Virgin Territory

Max is stunned to learn that her boyfriend, Gary, is a virgin. She has serious doubts as to whether she should deflower him, but eventually goes through with it. She is saddened when Gary heeds her advice and decides not to crowd her, but maintains her bravado in front of her friends. Kyle sees through her act and realizes that she is hurt, and she confesses that she can no longer simply chew men up and spit them out. Kyle takes her to dinner to talk things over. Khadijah, following Regine's suggestion, ""borrows"" some ski clothing for a weekend with Charles. Her plan goes awry when the store burns down before she can get a refund. Music: ""Teach Me Tonight"" by Al Jarreau