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.

Ben loses a patient to Oliver, then Oliver loses a patient to Ben. Meanwhile, Stewart and Lydia are audited by the IRS.

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.