Caroline in the City
Season 4
TV-PG
Caroline Duffy is a successful cartoonist living in Manhattan, whose comic strip "Caroline in the City" has become a huge hit. The strip is based on her own life, and the people in it--her occasional boyfriend Del and her best friend Annie. Aside from her career, however, Caroline's life is a mess, as is proven when she throws fruit out the window onto the street in a pathetic attempt to meet men.
Where to Watch Caroline in the City • Season 4
22 Episodes
- Caroline and the Guys in the Bathroom
E1Caroline and the Guys in the BathroomActing 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 Richard pause only long enough for Caroline to run to the bathroom to brush her teeth; but once there she is confronted by a vision of four men: ex-boyfriend Trevor, the first man she ever slept with, the high school coach she had a crush on, and the first little boy she ever kissed. An angry dialogue ensues, and an inflamed Richard, overhearing, strips down - only to be walked in on by an angry Annie, who accuses him of exploiting Caroline's vulnerable state. Then Caroline emerges from the bathroom naked, only to be confronted by Annie and Charlie, the latter having arrived with an urgent message from Del: Eagel Greeting Cards is going out of business. A mortified Caroline dresses and rushes to comfort Del, only to discover that he is celebrating the sale of his company to a major conglomerate, and to be pr - Caroline and the Office
E2Caroline and the OfficeWhen 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 sleeping there: his vengeful father-in-law has stripped him of apartments, possessions and credit cards, and Charley has been using Richard's old apartment as a makeshift hotel for visiting Russians. Then Richard falls afoul of the militaristic office manager Plum, who subjects him to standard employment tests, including a visit to the staff psychologist - who finds Richard's behavior a little odd. - Caroline and the Rotten Plum
E3Caroline and the Rotten PlumCaroline settles into her new workplace, where she inadvertently - and immediately - ticks off office manager Plum, who banishes Caroline and Richard to the basement. Meanwhile, Annie lusts after her yoga teacher Jonathan, but learns from Angie that he is a former porn performer. - Caroline and the Drycleaner
E4Caroline and the DrycleanerIt'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 cleaner to his dry cleaners' annual banquet, but when she attempts to strut both their stuff on the dance floor, she succeeds only in fracturing his leg. Meanwhile, since sales of her greeting cards are down, Del talks Caroline into attending a focus group which some wild new ideas about Caroline's cartoon strip. Richard is aghast to find Caroline seriously considering some of them (turning Salty into a dog, giving Caroline super-powers); then Del announces that all greeting card sales are down, Caroline's less than most. - Caroline and the Paper Chase
E6Caroline and the Paper ChaseDel 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 puppet show - about menstruation. While Annie is in her office, Caroline searches in Richard's desk for a highlighter and finds his divorce papers, and Richard angrily denounces her invasion of his privacy. Of course Annie immediately lifts the papers, is forced to hide them from Richard, sees them dumped down the corporate mail chute, and has to enlist Caroline's help to wheedle them back from the bizarre and hostile mail room staff - leaving a reluctant Richard and a strangely eager Charlie to act out the puppet show for Mr. MacDermott, who reveals that he is only doing the animated cartoon as part of a community service sentence. Discovering that the divorce papers are two months old but that Richard has not yet signed them, and is therefore technically still married, Caroline confronts him - and he confe - Caroline and the Bar Mitzvah
E10Caroline and the Bar MitzvahRichard'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 privilege. While an embarrassed Richard returns to Hebrew school, Caroline and Annie prepare a mocking party in his honor -- until Richard confesses to Caroline that he is doing it for the money only because he is humiliated by her having to pick up the tab for everything they do together. Meanwhile, Del gets a great deal in expensively tailored Italian suits, but won't admit they are several sizes too small for him. - Caroline and the Fright Before Christmas
E11Caroline and the Fright Before ChristmasIt's Christmas and people are becoming jaded. When Caroline decides not to celebrate Christmas, the others set out to change her mind, only to find out that she is one step ahead of them. But it doesn't quite go as expected. - Caroline and the Big Bad Bed
E12Caroline and the Big Bad BedCaroline 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 in temporarily with Richard. Meanwhile, Del and Annie forge a temporary truce and attempt to find dates for each other at the gym. Del strikes out, but Annie finds an obliging man mountain she'd ""like to hire a team of sherpas and climb."" - Caroline and the Horny Kid
E13Caroline and the Horny KidDel 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 who takes over Del's professional and personal lives with impressive competence. Meanwhile, Reg tries to convince Richard to sell his art, but the results are disastrous: a coffee house show is a fiasco, and when Richard desperately tries to emulate a subway hawker and sell his works to consumers, he is busted by an undercover cop who confiscates his art. - Caroline and the Firing Squad
E14Caroline and the Firing SquadCaroline 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 Del's career. When she persuades Del to let Charlie attend a planning meeting, the plan backfires big time: Charlie is fired. Charlie decides he wants to travel in Europe, and Del does the right thing and gives him the money for his Porsche as severance. Meanwhile, Richard gets Annie a job posing for a cartoonist who starts dating her, but the deal is fishy: it turns out he is only interested in her when she is dressed as the bizarre science fiction heroine of his strip. - Caroline and Joanie and the Stick
E15Caroline and Joanie and the StickCaroline 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. Meanwhile, a lonely Annie finds unexpected companionship with a smooth-talking parrot when she agrees to bird-sit for Dave, and Del has trouble accepting the fact that his new girlfriend Lisa is taller than he is. - Caroline and the Ancestral Home
E16Caroline and the Ancestral HomeCaroline 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 locals), and ultimately decides to preserve her childhood memories by buying the house herself. - Caroline and the 2000th Strip
E17Caroline and the 2000th StripThere'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 waits for her to get ready (Richard in a cheap rental tuxedo which gradually disintegrates), Caroline fantasizes about what life would be like if she retired. When she tearfully refuses to attend the banquet and does laundry instead, Richard gently points out that she has stopped writing about her real life in the strip (her fictional counterpart is ""still dating that veterinarian"") and perhaps it is time to bring her readers up to date -- and Caroline immediately draws a strip about their first date on the side of the washing machine. - Caroline and the Sudsy Guy
E18Caroline and the Sudsy GuyCaroline'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 learn that her former boyfriend Randy will be her new tenant. Meanwhile, Richard has his hands full in New York when he agrees to take Caroline's place by caring for Annie (who is sick) and Del (who thinks his girlfriend may be cheating on him). - Caroline and the Return of the Sudsy Guy
E19Caroline and the Return of the Sudsy GuySparks 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 his first real break as an artist when an eccentric gallery owner offers to exhibit his work -- but only if he can create another 'bleak' painting in time for the next day's show. - Caroline and the Ultimatum
E20Caroline and the UltimatumCaroline 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 worthiness of Caroline -- and when he is wheeled in by paramedics, he does indeed propose. - Caroline and El Niño
E21Caroline and El NiñoAfter 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, Richard shows up at the bridal shop with a bombshell announcement regarding his ex-wife: Julia has given birth to their son. Caroline gets an unexpected visit from Randy; and Annie and Del flirt with the idea of having a no-strings-attached fling.
