Jeb Barrows

Kate feels extremely threatened when Drew receives a call from Wendy, his recently divorced college girlfriend. Drew assures her that she has no reason to worry, and agrees to have lunch with Wendy. She tells him that she returned to town in the hopes of escaping an obsessive ex-boyfriend. She hasn't worked for years, but hopes that Drew can give her a job at the store to help her get back on her feet. He hires Wendy as his assistant, and tries unsuccessfully to hide the truth from Kate. Kate gets jealous and storms off. While at the Warsaw, Drew receives a call from a panicked Wendy, who fears that her ex-boyfriend has tracked her down. Mimi overhears and suspects that the whole thing is a ploy to get Drew into bed. Drew begins to agree with her after he arrives at Wendy's apartment to find her in her underwear. She claims that her radiator is broken. Even after Wendy's ex-boyfriend shows up, Drew still believes it is a scam. He changes his mind after the guy punches him.

As Lisa asks Jimmy to stand in and give her away when her father refuses to attend her wedding, Dave sets out to persuade her not to marry Johnny Johnson. However, Dave's efforts are set back when Johnny asks him to be the best man. And though Lisa admits that marrying Johnny is irrational, she still refuses to reconsider. Meanwhile, as Matthew throws a bachelor party at work, Dave agrees to be the best man, if only to keep the honor from going to Max. Once everyone arrives at Jimmy's estate for the wedding, Dave does his best to move things along to where he can object to the union. But even Dave's pointing out that the groom is a homeless drunk fails to derail the marriage. However, when he and Lisa are pronounced man and wife, Johnny is arrested and taken to jail when the ring he gave her turns out to be stolen. Although Jimmy offers the best lawyers money can buy, Johnny chooses to accept his punishment. Admitting that Dave was right all along, Lisa wants the marriage annulled. But when Dave makes a humorous observation about the bright side of having a husband in prison, she changes her mind. Finally, still unable to set aside her feelings for Johnny, Lisa takes everyone to the jail to finish the wedding, even as Dave tries getting her to reconsider one last time.