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.

Lydia is arranging a bachelor auction and Benjamin feels left out when his mother doesn't ask him to be in it. Oliver helps Lydia to set Regina up with a doctor she has interviewed, but they know it won't work if Lydia shows signs of support.