Caroline in the City: Season 4
Season 4 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 3.
- 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 4 Progress Shield
Caroline and the Guys in the Bathroom
Sep 21, 1998
Acting as narrator, the Elevator Lady brings us up to speed on the events at last season's close culminating in Richard and Caroline's first kiss. Desperately aroused, Caroline and
Caroline and the Office
Sep 28, 1998
When Carol can no longer stand the pressure Del is putting on her to work out of her new corporate office instead of her home, a reluctant Caroline discovers that Richard has been
Caroline and the Rotten Plum
Oct 5, 1998
Caroline settles into her new workplace, where she inadvertently - and immediately - ticks off office manager Plum, who banishes Caroline and Richard to the basement. Meanwhile, An
Caroline and the Drycleaner
Oct 12, 1998
It's just not Annie's day: she gets fired from Cats after eight years and is immediately dumped by her agent. To get back some self esteem, she agrees to go out with her dry cleane
Caroline and the First Date
Oct 26, 1998
On Halloween, Caroline and Richard go on their first date, but she's disappointed when she thinks he didn't plan anything special; Del fears he's going to be fired. MacDermott: Edm
Caroline and the Paper Chase
Nov 2, 1998
Del has hired Caroline and Annie to provide the voices for his new promotional video, but when he comes to pick them up it turns out they have to perform it for the boss first as a
Caroline and the Big Night
Nov 9, 1998
Caroline and Richard's big night finally arrives, in the form of a romantic weekend booked in the perfect room at the perfect country bed and breakfast. What's wrong with this pict
Caroline and the Diva
Nov 16, 1998
Jealousy between Richard and Annie reaches a new height when Richard wants to attend an operatic recital to which Caroline invited Annie months ago. The two squabble so childishly
Caroline and the Booby Trap
Nov 30, 1998
After Annie is beaten out in an audition by an untalented but well endowed rival, she announces her intention to have breast augmentation surgery during a Thanksgiving dinner alrea
Caroline and the Bar Mitzvah
Dec 14, 1998
Richard's Aunt Frieda announces that before she moves to Florida and wants to see Richard go through with the bar mitzvah he abandoned, and is willing to pay him $5,000 for the pri
Caroline and the Fright Before Christmas
Dec 21, 1998
Richard, Del and Annie are apparently successful in their combined effort to knock the Christmas spirit out of Caroline, but when she appears to have lost all interest in her annua
Caroline and the Big Bad Bed
Jan 11, 1999
Caroline becomes upset over what she sees as Richard's refusal to share his private life with her -- which comes to a head when Reg Preston's girlfriend kicks him out and he moves
Caroline and the Horny Kid
Jan 18, 1999
Del and Caroline participate in the company's mentoring program, but Caroline's adolescent charge Stan develops an embarrassing crush on her, while Del's turns into a teenage fixer
Caroline and the Firing Squad
Jan 25, 1999
Caroline is appalled to discover that Del (currently obsessed with buying a new Porsche) is paying his partner Charlie to stay at home so that his bizarre ideas won't compromise De
Caroline and Joanie and the Stick
Mar 8, 1999
Caroline tries to right an old wrong by giving up a romantic weekend in Boston with Richard to help out a visiting childhood chum, Joanie, whom Caroline once bullied in school. Mea
Caroline and the Ancestral Home
Mar 15, 1999
Caroline and the gang visit her family's home in Wisconsin and learn her parents are selling the house. Distraught, she prolongs her stay (while Richard unwillingly bonds with the
Caroline and the 2000th Strip
Mar 8, 1999
There's to be a big celebrity banquet to celebrate Caroline's 2000th strip, but there's a snag: Caroline is completely blocked in terms of fresh, funny ideas. While everyone else w
Caroline and the Sudsy Guy
Mar 22, 1999
Caroline's plans to rent out her house in Wisconsin hit an unexpected snag when Grandma Duffy refuses to leave, forcing Caroline to return to Wisconsin, where she is surprised to l
Caroline and the Return of the Sudsy Guy
Mar 29, 1999
Sparks fly between Caroline and Randy when he pays her a surprise visit in New York and they end up getting stuck together in a subway tunnel for two hours. Meanwhile, Richard gets
Caroline and the Ultimatum
Apr 5, 1999
Caroline gives Richard a matrimonial ultimatum; but on his way to propose to her, he is taken hostage in a video store holdup. He decides that escape will prove his manhood and wor
Caroline and El Niño
Apr 26, 1999
After deciding they can't wait to get married, Caroline and Richard plan their nuptials for the following week. But while Caroline and Annie search for the perfect wedding dress, R
Caroline and the Big Move
Apr 26, 1999
As Caroline and Richard prepare to leave for Italy to visit his newborn son, Richard makes a confession that gives Caroline second thoughts about their future together: he never wa