Lisa mistakingly believes she's been dumped by Dave, which Andrea finds out about and leads to an investigation of the relationship. Andrea deludes herself into thinking she and Lisa and friends. Bill causes Mr. James legal trouble after suggesting foreign diplomats be dragged out from cars and beaten for not paying parking tickets, and one subsequently is. Beth and Joe discover Matthew has a real talent.
As the new boss, Lisa attempts to make a good first and serious impression on the staff, which ends in epic failure. Dave, trying to get his job back, decides to become "Pure evil" and unleash Bill, which doesn't bring the results he hoped for. Matthew is now living in Lisa's office, having been kicked out of his apartment.
Lisa and Beth try to find out why Matthew has gotten a brother from the Big Brothers Big Sisters of America. Dave seemingly becomes paranoid when Bill suggests Lisa has a secret new boyfriend, which leads Bill, Joe, and Mr. James on the hunt for whom the guy is.
Using information secretly collected by secret office observers, Mr. James notices Dave and Lisa's productivity levels were higher when they were dating, so Mr. James set out to try and get them back together, but when that fails, Bill steps in. Mr. James gets Matthew a small red car for his birthday, which he drives around the building and meets a girl with.
After a co-worker nobody knew dies in a freak incident involving a copy machine Joe modified, Joe blames himself for the man's death. An old college friend of the departed shows up wanting to know more about Ted, and the staff, lead by Bill, make up lies.