Oliver, Regina and Lydia all decide to use family members for their own personal gain. Meanwhile, Stewart tries to find a way to get Ben to take his lazy housekeeper.

Stewart ends up being named one of the city's top doctors by a Manhattan magazine. However, he is less than thrilled when his old rival shows up at his celebration party with none other than Lydia.

At the funeral of an uncle, Oliver and Ben meet a girl they both were in love with when they were kids. When she calls the next day and leaves a message to meet for a date, no one knows whom she meant and both are convinced to be the one she asked for. Meanwhile, Lydia and Stewart are arguing about what their inheritance might be.