Caroline in the City — Season 2

Caroline starts dating her cat Salty's vet. Richard fails at being an artist in France and returns to New York.

Richard goes out of his way to recover the letter he left for Caroline before she sees it.

Annie gets audited by a man who is an extreme Cats fanatic. Richard has overly-amourous neighbors that keep him awake all night. Caroline isn't sure what to do when Joe says he finds it weird that she's still friends with her ex Del.

Caroline freaks out when Joe says "I love you" way too soon. Richard inherits a car but doesn't know how to drive.

Del stands up to his father who owns the greeting card company, resulting in Del being fired. Del decides to start his own greeting card business and tries to coerce Caroline to be one of his first clients. Richard is hired to paint a mural in a seedier area of the city.

Del pretends to be Jewish to date a woman who will only date Jewish men. Joe refuses to go to an award show where Caroline won an award because one of the sponsors uses animal products.

Annie dresses up as a man for an audition. Richard needs surgery and gets nervous before the operation.

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

Joe recommends a therapist for Salty, Caroline's cat. The cat therapist in turn says Salty's problems are due to Richard.

Annie's parents split up and her mother suddenly moves in with her. Richard takes a temporary holiday job. Charlie and Del think their new assistant is a deranged killer.

Del tries to get Richard to draw some greeting cards based on a porcupine doodle, but Richard fears it would be selling out as an artist. Caroline gets locked in the laundry room overnight with a bum.

Richard gets a huge piece of marble to chisel his own art, which he does in Caroline's living room. Joe's ex-girlfriend returns from traveling, and Caroline discovers they still live together.

Annie's sister Donna visits, looking to revive her singing career. She stumbles on the letter that Richard wrote to Caroline that Annie still has, and turns it into a song to Richard's dismay. Del and Charlie get snowed in inside Del's porsche.

In a scheme to date a woman, Del agrees to have one of Richard's painting hung at his club. Richard isn't impressed when he sees where.

Caroline drags Richard to a Knicks basketball game, where his seat is selected for a chance to win $100,000 by making a free throw shot.

Learning artists sell more after they die, Caroline inadvertently forces Richard to fake his own death to sell some artwork.

Annie and Caroline go on a trip together with an agreement to not allow men to get between them. Richard has a date with a philosophy student that he thinks he's connecting with, but Charlie and Del unintentionally interfere.

Charlie keeps seeing monkeys outside everywhere. Caroline attempts to learn to go out alone. Del dates Annie's friend, who happens to be a pyromaniac.

Del asks Caroline to come along as the artist talent when he tries to steal one of his father's clients. The client thinks Caroline is there for other reasons. Annie has problems with Richard's relationship with her mother.

Caroline helps an elderly neighbor but the lady starts taking advantage of her. Things come to a head when she asks Caroline and Annie to help her take her naked dead husband to a funeral home. Richard tries to sell his car.

Caroline takes Richard with her to find out why a small newspaper dropped her strip. Annie plots revenge on a theater critic who poorly reviewed her, getting Del and Charlie involved.

Caroline inadvertently hires someone to "talk to" her building supervisor when her shower is broken for over a week. Annie's manager is hoping to get some publicity when Annie saves a man's life, but the man isn't willing to go along with it.

Caroline is to appear on The Tonight Show With Jay Leno, but things don't go well when she discovers she may have accidentally been in contact with LSD. Del tries to teach Richard how to pick up women, and Richard ends up trying with what turns out to be the past love of his life.

Richard's long-lost love Julia is getting married in two days. Unsure how to react, Richard pretends he is married already to Caroline. Del is going bankrupt as his greeting card business isn't as successful as he'd hoped. Annie gets a part in a pilot for a new TV show.

Julia comes to Caroline's apartment in tears, still believing she and Richard are married, telling them both that her engagement is off. Annie has problems with her character as she films the show's pilot episode.