Harry takes an Italian family to their grandmother’s birthday party, only to become dismayed when none of them actually wants to attend. When Harry reminisces about his own grandmother, everyone learns a lesson about the importance of family.
Harry is about to ask Wendy out when he finds a child’s toy left in the back seat of his car. He wastes the whole day, and risks serious consequences, trying to find its owner, only to discover that the world is not the way he imagines it.
Harry is delighted to discover that his passenger is a boy on the autism spectrum just like him. Unfortunately, Harry tries to use his experience to coach the boy about how to talk to people at parties, only to make the boy hysterical.
Harry is intimidated when a pair of boisterous rappers hire him as their personal after-party driver for a night. But, when they learn about Harry’s feelings for Wendy, they insist on helping him win her heart—whether he’s ready or not.