Successful New York cartoonist Caroline Duffy, author of comic strip called Caroline in the City, hires an uptight artists Richard as the colorist. With her midwest approach she just can’t help trying to change his cynical mind.
The marriage of Richard and Julia is over, so he finally can be with Caroline. Del sells his business to a large company which forces Caroline to work in the office building.
Caroline meets Randy, guy she used to go to school with, which puts a strain on her relationship with Richard. At the end of the season Richard moves to Italy to take care of his son from marriage with Julia and Caroline is left alone in New York.
1 | Caroline and the Guys in the Bathroom |
| Caroline and Richard savoring their first passionate kiss and preparing for romance. But the moment is spoiled when Caroline gets a series of unexpected visitors - some real and some imagined -- and even more unexpected news regarding her future with Eagle Greeting Cards. |
2 | Caroline and the Office |
| Vengeful father-in-law Mr. Mazzone strips Richard of all his worldly possessions, forcing Richard to take temporary refuge in Caroline’s new office. |
3 | Caroline and the Rotten Plum |
| After Caroline inadvertently offends office manager Plum, she and Richard are banished to a damp, dark basement office. |
4 | Caroline and the Drycleaner |
| After Annie loses her boyfriend, her job and her agent, she impulsively accepts a date with her local dry cleaner and spends an evening to remember. Del organizes a focus group to determine why Caroline’s greeting card sales are down and, much to Richard’s dismay, Caroline takes their off-the-wall suggestions to heart. |
5 | Caroline and the First Date |
| Caroline and Richard decide to go out on their first official date together on Halloween, but their romantic evening turns into fright night when Richard gets himself into a rooftop jam. |
6 | Caroline and the Paper Chase |
| Caroline’s curiosity gets the best of her when she stumbles across Richard’s divorce papers in his desk drawer, but an office mishap sends her on a frantic paper chase to retrieve the documents after they are lost in the interoffice mail. |
7 | Caroline and the Big Night |
| Caroline and Richard’s relationship reaches a turning point after three years when they finally decide to consummate their relationship. |
8 | Caroline and the Diva |
| Caroline invites Richard and Annie to the opera, which turns sour whern she inadvertently disrupts the diva’s performance. |
9 | Caroline and the Booby Trap |
| Tired of losing acting roles to other, more well-endowed women, Annie surprises the gang on Thanksgiving Day by announcing that she plans to get breast implants. |
10 | Caroline and the Bar Mitzvah |
| Richard gets an offer from his aunt who promises to give him $5,000 as a Bar Mitzvah gift if he agrees to finally go through the ceremony. |
11 | Caroline and the Fright Before Christmas |
| Tired of being the brunt of their holiday jokes, Caroline tricks Richard, Del and Annie into taking a road trip to Christmasville to help them recapture their Christmas spirit. |
12 | Caroline and the Big, Bad Bed |
| Richard agrees to let Reg become a houseguest after the cartoonist has a fight with his girlfriend. But the arrangement soon causes a rift between Richard and Caroline when he allows Reg to remodel the apartment, but refuses to accept a simple bath mat from Caroline. |
13 | Caroline and the Horny Kid |
| Caroline and Del experience mixed results when they become office mentors to a young cartoonist with an overactive libido and an eager marketing student with a knack for cleaning up Del’s messy social life. |
14 | Caroline and the Firing Squad |
| Caroline tries to take Charlie under her wing and teach him the fundamentals of life after Del is forced to fire him. |
15 | Caroline and the Ancestral Home |
| Caroline with Richard and Annie visits Pestigo, when her parents tell Caroline that they are selling their house. |
16 | Caroline and Joanie and the Stick |
| Caroline tries to right an old wrong by giving up a romantic weekend in Boston with Richard to help out a visiting childhood friend, Joanie. |
17 | Caroline and the 2000th Strip |
| Caroline draws a blank while trying to create her 2000th comic strip, and her anxiety provokes an imaginative series of vignettes depicting what her life would be like if she wasn’t a cartoonist. |
18 | Caroline and the Sudsy Guy |
| Caroline’s plans to rent out her house in Wisconsin hit an unexpected snag when her grandma 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. |
19 | Caroline and the Return of the Sudsy Guy |
| 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. |
20 | Caroline and the Ultimatum |
| Caroline gives Richard a 7 p.m. deadline to make a marital commitment to her, then is coerced into spending the day making pottery with Del and Annie while she anxiously awaits his decision. |
21 | Caroline and the Il Nino, part 1 |
| 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, Richard shows up at the bridal shop with a bombshell announcement regarding his ex-wife. |
22 | Caroline and the Il Nino, part 2 |
| 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. |