When Maggie brings Mickey to Dr. Fleisher (Elliot), Maggie is introduced to Elliot's old college friend Gary. With a very mutual interest in each other, Maggie and Gary decide to go out on a date. However, the idea bothers Elliot who still has been working up the nerve to ask Maggie out. Gary and Maggie have several successful dates, which leads to Maggie wondering if he is the right guy for her. But Gary's true face is revealed when Mickey and Gary are left alone - he does not like children and plans to send Mickey away to a boarding school when he and Maggie end up together. Gary's true personality shines through when Mickey experiences a serendipity, and catches his first fever. Maggie becomes ultra anxious to this new experience and ask for Gary's help. But he does not lend a very helping hand in return. Maggie eventually gets a hold of Elliot, who easily comes to the rescue and saves Mickey's health and Maggie's nerves.

• Amy Heckerling
• Ed. Weinberger

• Mary Page Keller
• George Clooney
• Amy Hill