George's new housekeeper Margie turns out to have boyfriend problems. He offers advice, and she so appreciates his support that she moves in with him, much to the delight of his nosy neighbors. Unfortunately, the girl's family isn't quite so excited, and George's joy over his young, beautiful and meticulously neat housekeeper is short-lived, after Leo has a miscommunication with the girl's overprotective dad. Meanwhile, Leo, in an effort to help Ted, becomes the restaurant industry's worst food buyer.

George hosts a tour of his home in period costume in hopes of becoming President of the Historic Conservancy, but his high hopes of finally winning the annual historic house tour end in a drunken haze after Leo and Ambrose spike the egg-nog.

Every week, George loses himself in a poker game with friends. But when Leo finds out that Walt, his supposed best friend, is also part of these weekly sessions, Leo is bitten by the jealousy bug and demands to be included. Meanwhile, Ted agrees to be hypnotized by Ambrose in order to deal with his squeamishness about the delivery room.

While he is reminiscing about Casey's childhood on the eve of her baby shower, Leo remembers that he convinced his old friend Robert Goulet to sing her a song on her seventh birthday. Eager to make a big splash at the shower, Leo tries to get Goulet, who is making a guest appearance at George's bookstore, to sing for Casey again. Unfortunately, this time, the song produces more than just applause.