Caroline in the City: Season 2
Season 2 Lore Primer
Key plot threads, lore context, and character stakes you need to remember before diving into this season.
- Directly follows the overarching narrative developments of Caroline in the City Season 1.
- Faction dynamics and core character alliances shift under escalating external stakes.
- Crucial mysteries introduced previously reach key turning points and narrative reckonings.
- Sets up serialized story arcs that build directly toward the climactic season finale.
Episode Guide
Season 2 Progress Shield
Caroline and the Younger Man
Sep 17, 1996 · 22 min
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 w
Caroline and the Letter
Sep 24, 1996 · 22 min
Realizing Caroline never received his love letter, Richard labors to retrieve it from her friend's apartment.
Caroline and the Cat Dancer
Oct 15, 1996 · 22 min
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
Caroline and the Guy Who Gets There Too Soon
Oct 22, 1996 · 22 min
Realizing Caroline never received his love letter, Richard labors to retrieve it from her friend's apartment.
Caroline and the Dreamers
Oct 29, 1996 · 22 min
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 immediat
Caroline and the Nice Jewish Boy
Nov 12, 1996 · 22 min
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 ba
Caroline and Victor/Victoria
Nov 19, 1996 · 22 min
Annie poses as a man to prepare for a ""Victor/Victoria"" audition.
Caroline and the Comic
Nov 26, 1996 · 22 min
Richard's father asks for his son's help in reviving an old comedy routine.
Caroline and the Therapist
Dec 3, 1996 · 22 min
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,""
Caroline and the Red Sauce
Dec 10, 1996 · 22 min
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
Caroline and the Freight King
Dec 17, 1996 · 22 min
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 o
Caroline and the Perfect Record
Jan 7, 1997 · 22 min
Caroline's romance is beached when Joe's ex returns from an environmental mission.
Caroline and the Singer
Jan 14, 1997 · 22 min
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 inspira
Caroline and the Kept Man
Jan 21, 1997 · 22 min
Caroline's romance is beached when Joe's ex returns from an environmental mission.
Caroline and the Long Shot
Feb 11, 1997 · 22 min
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
Feb 18, 1997 · 22 min
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 se
Caroline and the Getaway
Feb 25, 1997 · 22 min
When Caroline calls her out on always blowing her off for male dates, Annie makes a deal: they will go away together for a weekend skiing trip and ignore men. Naturally, both immed
Caroline and the Monkeys
Mar 11, 1997 · 22 min
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, Car
Caroline and the Buyer
Apr 1, 1997 · 22 min
Del asks Caroline to help him woo one of his father's biggest clients, a greeting-card store magnate who misunderstands what the cartoonist has to offer. Meanwhile, Annie resents R
Caroline and the New Neighbor
Apr 8, 1997 · 22 min
Things get a little stiff when an demanding elderly new neighbor, who is driving an initially sympathetic Caroline nuts, asks Caroline and Annie for a really big favor - to help ou
Caroline and the Critics
Apr 15, 1997 · 22 min
When Caroline learns that an obscure upstate newspaper has dropped her syndicated strip, she drives up with a reluctant Richard to find out why. Naturally Richard's car breaks down
Caroline and the Ombudsman
Apr 22, 1997 · 22 min
Caroline's having a really bad hair week because her shower's been out of commission for several days and she can't get the super in her building to repair it. A deliveryman at Rem
Caroline and the Bad Trip
May 6, 1997 · 22 min
A funny thing happens to Caroline on the way to "The Tonight Show"; Charlie thinks he's found his father.
Caroline and Richard & Julia
May 13, 1997 · 22 min
Richard's long-lost love arrives with bad news: she's getting married in two days, to arrogant and insanely jealous fashion designer Marcello. Not to be outdone, Richard concocts a
Caroline and the Wayward Husband
May 13, 1997 · 22 min
Richard prepares to run off with another just as Caroline is about to tell him how she feels.