A bored suburban husband finds his affair with a high-school babysitter fast snowballing out of control in this black comedy from first-time screenwriter/director David Ross. Shirley (Katherine Waterston) is a brainy honors student who is always thinking about the future, and works part-time as a babysitter in order to save up for college. Among Shirley's regular charges are spirited youngsters Adam and Mikey, the offspring of respected father Michael (John Leguizamo) and his pretty wife, Gail (Cynthia Nixon). Shirley has always had an innocent crush on Michael, but one night after her regular shift, things take a serious turn when the pair sneaks a furtive kiss. Lately Michael has become noticeably depressed by the suburban routine, longing for the days before family responsibility weighed him down and his wife turned into the typical minivan-driving soccer mom. Shirley's kiss makes Michael feel alive again, and as a result he gives her a substantial tip that night. Before long, however, a fleeting kiss has turned into a full-fledged affair, with Michael and Shirley using the babysitting shifts as cover. When Michael's married friends catch wind of his extramarital exploits, they, too, express the want for a babysitter who is willing to earn a healthy tip. Recognizing the potential for profit in such a situation, Shirley soon assumes the role of teenage madam -- matching up her high-school friends with otherwise upstanding men who have grown bored with married life. Of course, Shirley isn't above skimming a bit of the profits for her college fund, but then again it's only a matter of time before their carefully crafted cover is blown.