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Caroline Duffy is a successful cartoonist in Manhattan, whose eclectic friends are sometimes the subjects of her comic strip.

Set in a New York diner called Union Square, this sitcom tells the story of a lawyer turned playwright, an aspiring actress who just got to the Big Apple, an ex-con, an absent-minded waiter, and a neurotic real estate broker.

Caroline and Richard are just about to leave for Boston when an old classmate of hers drops in unexpectedly. Caroline feels guilty because she used to bully her. Annie becomes attached to a macaw that she is looking after.

Julia, Richard's old girlfriend, has returned with the news that she is getting married. He tries to impress her by asking Caroline to act as his wife. Then it becomes a game of oneupmanship between Julia and Richard.

Richard's mother arrives for a visit with a few stories to tell, causing Richard a lot of embarrassment. She also has a tendency to exaggerate her life. After a lot of prompting, Del decides to have a pedicure and ends up addicted.

Annie wants to be Julie Andrew's understudy in Victor/Victoria and 'kidnaps' her in order to get an audition. She then practises being a man to get the part. Richard very reluctantly has to go hospital to get a polyp removed.

Caroline picks at her nose in front of the camera at a malfunctioning ATM and is embarrassed to ask the manager for the money it didn't dispense. Richard is having a lot of difficulty breaking up with his girlfriend, Shelly.

Caroline and Richard going home for her parents fortieth wedding anniversary. Caroline is then very upset when she hears the news that her parents are selling their home, so she is determined to buy it.

Caroline injures her back playing racquetball and takes some of Annie's pain killers that knock her out. She has a deadline for the next cartoon looming so Del and Richard collaborate to finish it.

Caroline picks up a man she met in a clothes store and their date is a disaster. Del and Richard have a date with models and they don't turn up.

Caroline is to appear on The Tonight Show to publicise her new book. She accidentally takes some drugs before going on. Talk of who Richard's father is means Charlie goes looking for his. Del tries to give Richard some dating tips.

All the gang get together to walk a 'Caroline in the City' balloon in the Thanksgiving Day parade. Unfortunately, Shelly's actions result in the balloon being released and subsequently causing havoc.

Richard's aunt visits him and wants him to do his Bar Mitzvah. To make him interested, she offers him $5000 to do it. Caroline is unhappy he is taking the money. Del is worried about his image so he keeps buying suits that are too small.

Annie and Del have a pact to go to the gym to help each other find a paramour. A workmate needs a place to stay so Richard offers to let him use his apartment. When he tidies the place up, Richard is happy and Caroline becomes unhappy.

Richard needs to be closer to his son and wants to go to Italy. However, the issue of having children splits up Caroline and Richard. Then Randy turns up in New York. Meanwhile, the romance between Annie and Del heats up.

Caroline is particularly excited as she and Richard are going away for their first weekend together. It starts off badly when they get the wrong room because it has two single beds and no bathroom. Caroline tries to change their rooms.

When cleaning up his apartment, it comes out that Richard is a music composer. He was taught by Marvin Hamlisch and it appears that Marvin stole one of Richard's tunes. Caroline meets an old boyfriend, but then there is the dog.

Annie is going to her 10 year high school reunion intent on revenge. When her date falls through she goes with Del, complete with an elaborate story. Julia sets up Caroline on a blind date but she doesn't want to go, until she sees him.

Annie is tired of missing out of acting roles and decides that she needs to have her breasts enlarge. When Richard says he would like Caroline to have bigger breasts, she decides to investigate breast enlargement as well.

Both Caroline and Del are organising their respective attendants for the wedding but it is not going smoothly. Annie, especially, is having trouble coping with her maid of honour responsibilities.

Annie's mother is driving her crazy. Caroline finds out that some stores are no longer stocking her cards. Del works out a plan and takes the store owner out for a dinner with Caroline, but he misinterprets what she is offering.

Del decides to sell celebrity hair when Annie gets a hairdressing appointment at a celebrity hairdressers. Caroline reports a rude cabbie but Richard fails to turn up as a witness when he becomes addicted to a computer bulletin board.

Caroline and Joe are getting on and Del is envious. Annie is audited by the IRS. When the auditor finds out she is in Cats he offers to go easy on her if Annie gets him an audition for Cats.

A cereal company wants to produce 'Sweet Caroline' breakfast cereal. However the shape turns out looking like a part of the female human body. Del wants to learn to dance for his wedding with Caroline and asks Annie to teach him.

Caroline and Del are try going for a holiday vacation together but all they do is break up. Caroline wants revenge. Richard tries to break up with Shelly by getting Charlie to take her out. Things don't go as planned.