Air date: 9/17/96

Three months have passed, and Caroline is thinking about advertising for a new assistant, so Charlie tries to demonstrate he would be perfect for the job and knocks Salty out the window. Sparks fly between Caroline and the vet who treats Salty, despite her fears that at 24 he is much too young for her. Meanwhile Richard, having failed as an artist in Paris (his only customer is knocked into the Seine just before buying some paintings), returns to New York and is forced to take a menial job in an ice cream parlor, where he just misses seeing Caroline on her first date with Joe, during which they helped raid an animal experimental laboratory and were arrested. Caroline wakes up in bed with Joe and is unable to sneak out before he wakes and demands to see her again that evening, and on her way home she and Richard suddenly meet face to face.

Caroline and the Letter

Air date: 9/24/96

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

Caroline and the Cat Dancer

Air date: 10/15/96

Richard tries to adjust to his new apartment, where he is plagued by noisily amorous neighbors; Joe tries to adjust to the fact that Caroline plans to remain friends with Del; and Annie frantically tries to adjust her financial records when she is notified that the IRS is auditing her for 1993, a year she barely remembers. Her bad-tempered auditor is under fire for being too lenient with his clients, but when he learns she is a dancer in Cats, he strikes a deal: she'll "never have to pay taxes again" if she can get him an audition for the show. Enter 'producer' Del and 'director' Charlie. Meanwhile, disturbed by Joe's jealousy, Caroline makes up her mind to break a date with Del by telling him she's been called out of town.

Caroline and the Guy Who Gets There Too Soon

Air date: 10/22/96

When Joe tells Caroline he loves her on a date to an orchard she doesn't know how to handle it so avoids answering. She decides to go on a date with an older man and Joe finds out, forcing Caroling to make a decision about whether to keep dating Joe or not. Meanwhile Richard inherits an old car but has never learned to drive so plans to sell it. Annie won't let him so she can borrow it, which leads Del and Annie to try to teach him how to drive.

Caroline and the Dreamers

Air date: 10/29/96

Upset that Caroline's strip is not being merchandised aggressively, Del finally stands up to his father who promptly replaces Del as president with his sister, who in turn immediately fires him. Excited about forming his own company (with Charlie as his sole employee), Del assumes that Caroline will jump ship with him, particularly as he kept forgetting to renew her contract with his father's company. When Del calls his former cartoonist clients to a meeting in his crummy new office, they promptly desert him, leaving Caroline in the lurch how can she tell Del she values her income more than their friendship? Meanwhile, Richard is excited about being chosen to paint a mural for the city, even when he discovers he was the only applicant, but he's not prepared for the hostile reaction by the local denizens of the 'hood in question. He finally wins them round by agreeing to incorporate both Dennis Rodman and one hood's girlfriend into the mural, and even Annie is impressed at the unveiling. Then a demolition crew arrives and Richard realizes he painted the wrong building.

Caroline and the Nice Jewish Boy

Air date: 11/12/96

Joe refuses to accompany Caroline to an award ceremony because one of the sponsors uses animal products; so she calls former date Willard, whom she dumped because he was fat and balding. After Charlie takes him to a Jewish singles event by mistake, Del lies about his background to date an attractive woman who parents will only allow her to date Jewish men. Willard shows up a reformed hunk who only came to tell Caroline to go to hell - "And I'm rich, too!" Aghast that Del plans to tell Risa the truth only after they spend a weekend together, Caroline points out delicately that if they sleep together Risa will know only, because Del is a "turtleneck kind of guy." So Del books himself into hospital, telling Risa he needs his "tonsils" removed; but she shows up to confess that she is eloping with her former boyfriend, who isn't Jewish either. A reluctant Richard escorts Caroline and even more reluctantly dances with her. Just as they seem about to have a tender moment, Joe appears, having decided Caroline's triumph is more important than his principles - and Richard walks home alone.

Caroline and Victor/Victoria

Air date: 11/19/96

Annie poses as a man to prepare for a "Victor/Victoria" audition.

Caroline and the Comic

Air date: 11/26/96

Richard's father asks for his son's help in reviving an old comedy routine.