Realizing Caroline never received his love letter, Richard labors to retrieve it from her friend's apartment.

When a doodle of a porcupine drawn by Richard gets into a stack of Caroline's greeting card designs by mistake, Del tries to convince Richard to develop the idea into a character of his own - but Richard protests that he is a real artist, not a cartoonist, throwing Caroline for a loop. Annie can't seem to shake a recurring five dollar bill with ""Repent"" written on it, and her mother tries to convince her it's a sign from God that she should return to the Church. When Caroline accidentally gets locked inside the laundry room overnight, her encounter with a bum who used to be a trucking magnate convinces her she has made the right career choice. Richard succumbs to Del's monetary temptation and produces a series of increasingly gloomy and unusable porcupine cards; and he finally apologizes and admits that he admires Caroline's professionalism as a cartoonist. Meanwhile, when a telegram stripper shows up at Del's office by mistake (she was supposed to be at a law firm), Del hires her as r

Del hopes to spark up romance with Annie's neurotic friend Cassandra, who plans on lighting a fire of her own - she's a compulsive pyromaniac just of an institution. Meanwhile, Caroline spends a night out on the town ""alone,"" crashing the restaurant where Richard is trying to enjoy a quiet meal and ultimately being forced by him to attend a movie on her own. Meanwhile, Charlie keeps spotting monkeys throughout Manhattan, and becomes convinced they are taking over the city.

Caroline and Annie are overjoyed to learn that Caroline's agent has arranged for her to promote her new book on the Jay Leno show; then Annie reminds Caroline that she will need an entertaining story to tell. Enter Richard's mother Natalie, carrying a jacket that belonged to Jerry Garcia and revealing that the dead rocker was Richard's real father. But Richard, hiding in the stairwell until his mother leaves, isn't impressed: there's hardly a celebrity that Natalie hasn't maintained fathered him. While Caroline and Annie fly to Los Angeles, Del tries to teach Richard how to pick up women during Happy Hour at Remo's (Richard: ""I'm not sure I can do that - I mean, be happy for a whole hour.""), and Charlie goes in search of his father, whom an adoption agency locates instantly: a bumbling waiter in a fashionable restaurant who is overjoyed to meet Charlie, even though their reunion gets him fired two weeks before his retirement. While waiting to appear with Leno, Caroline is warned that s