Air date: 12/3/96

When Salty begins behaving oddly, Mark recommends that Caroline consult a cat therapist. Although the woman is a complete fruitcake "not allowed to practice on people any more," she accurately pinpoints the problem as Richard's fear of caring for animals. He confesses that he suffered a childhood trauma at the hands of his teacher, Mrs. Fox, when both the class gerbil and rabbit died while in his care and she condemned him as an "animal killer." Annie, who has been fixed up by her mother on a blind date with a peculiar forest ranger, helps Caroline track down the retired Mrs. Fox and convince her to make amends with Richard. This doesn't work out quite as planned, since Mrs. Fox also bites the dust.

Caroline and the Red Sauce

Air date: 12/10/96

Annie's mother arrives unexpectedly and moves in with her, to her mounting dismay, but refuses to tell her why - then confesses to Caroline that she has left Annie's father. Annie demands a showdown with her father, who in turn confesses that this is no ordinary spat: he is in love for the first time in his life with another woman. Meanwhile, Richard takes a temporary job as a gift wrapper for Macy's, but his bad attitude gets him demoted to elf; and Del and Charley become convinced that their new assistant is a psycho killer, since all the people on her resume turn out to be dead.

Caroline and the Freight King Air date: 12/17/96

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.

Caroline and the Perfect Record Air date: 1/7/97

Caroline's romance is beached when Joe's ex returns from an environmental mission.

Caroline and the Singer

Air date: 1/14/97

Annie's sister Donna, who has come to town in hopes of reviving her singing career, discovers Richard's secret love letter to Caroline (inside Annie's diary) and uses it as inspiration for a new song, to Richard's horror and Annie's fury, since she has been using the letter to blackmail Richard into taking her mother to electrolysis appointments. Caroline is preoccupied with her perfect plain black pumps, which she left in Joe's apartment; after a fruitless quest to replace them, she sneaks in to retrieve them, and is found by a repentant Joe. Meanwhile, Del and Charlie get snowed in - inside Del's Porsche, with the keys and his cell phone locked in the trunk by Charlie.

Caroline and the Kept Man

Air date: 1/21/97

Caroline's romance is beached when Joe's ex returns from an environmental mission.

Caroline and the Long Shot

Air date: 2/11/97

Richard wins a chance to make his dreams come true by sinking a $100,000 three-pointer during a Knicks game.

Caroline and the Dearly Departed

Air date: 2/18/97

It's not a pretty picture when Caroline persuades reluctant con-artist Richard to fake his own death in order to catch the eye of a wealthy art dealer who's scouring the city in search of the works of dead painters - and who winds up delivering the eulogy at Richard's fake funeral.