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.