Season 1, Episode 1: Pilot21 September 1995
Caroline advertises for a colourist and employs Richard. Her former boyfriend, Del, has moved on and Caroline is under pressure to also get a date. Richard steps in at the last moment to allow Caroline to save face in front of Del.
28 September 1995
Richard is mugged and Caroline helps him by buying him a new wallet. On the return journey, he and Caroline catch the mugger and he is arrested. The mugger turns out to be a small guy and Richard thinks of himself as a bit of a wimp.
5 October 1995
Caroline manages to get Richard's work displayed at an art gallery. They later find out it only shows works by gay artists. When Richard hears that the painting could sell for $20 000, he pretends that he is gay.
12 October 1995
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.
19 October 1995
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.
2 November 1995
Caroline finally agrees to meet Del's mother whom she's been avoiding because she thinks that his mother is a difficult person. She arrives at Remo's Ristaurante, but Del is stuck on the subway and hasn't yet arrived. Caroline spots a haggish woman and mistakes her for Del's mom. Intimidated, she hides out in the kitchen until Del arrives. Annie discovers that Richard is spending his birthday alone and she tries to help him celebrate.
9 November 1995
Caroline's auntie, Mary, arrives for a visit and sets her up with a date. Caroline takes him to the opera when Del doesn't want to go, which makes Del very jealous. He resorts to extreme actions to win her back.
16 November 1995
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.
7 December 1995
Caroline's apartment is broken into and her suspicion falls on Annie's new boyfriend, who has just been released from prison. Annie is upset at Caroline but they have to find out who is correct.
14 December 1995
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.
4 January 1996
Richard starts a second job painting portraits. Caroline tries to return earrings that Del gave her for Christmas but it leaves her with a dilemma. At a party, Annie makes a date with a man but can't remember what he looks like.
11 January 1996
Richard is a finalist to paint a mural. The person who makes the decision is very interested in Caroline and Richard sets them up on a date. However, Richard finds out some further information that puts him in an ethical dilemma.
25 January 1996
Caroline returns to home her town of Peshtigo, Washington after it decides to dedicate a park to her and there is some sibling rivalry with her brother. Annie gives her role to her understudy so that she can dance in front of her parents.
1 February 1996
Caroline buys an old desk and finds an engraved watch in a locked drawer. She sets out to find the secret of the watch. One of Del's employees dies and he finds out some unpleasant facts about him.
15 February 1996
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.
22 February 1996
Del has proposed to Caroline but she is unsure about whether to accept. Richard looks for a new job and is seduced by the employment counsellor. Caroline finds them together, which changes everything.
14 March 1996
For charity, Caroline offered to paint a Caroline mural and it turns out to be for a self-indulgent 10 year-old boy. Del has trouble coping when one of Caroline's old boyfriends from Italy pays a visit.
28 March 1996
Caroline and Del go to Del's country house only to find his second ex-wife is staying there with her new boyfriend. Annie's brother is employed to repair Richard's light switch and it starts a family feud.
4 April 1996
Del's car is impounded but he has difficulties getting it out of the impound yard. A movie is being shot outside Caroline's apartment. Annie, Caroline and Richard volunteer to be extras but the results do not turn out well.
18 April 1996
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.
25 April 1996
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.
9 May 1996
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.
16 May 1996
Preparations are speeding up with the wedding only days away. Richard writes a love letter to Caroline and puts it in her apartment but she doesn't receive it. He unsuccessfully tries to retrieve it so he suddenly leaves.
5 August 1996
Caroline has writer's block so this episode has Richard and Caroline looking back on some of the events in Season 1. This includes the time Caroline was caught shop lifting some condoms.
17 September 1996
Three months after Caroline had pulled out of her wedding, Richard is in France painting. He is unsuccessful, returns home and starts work in an ice cream parlour. When Salty is injured, Caroline ends up dating the much younger vet.
24 September 1996
Richard finds out that Caroline didn't read the letter he left her so he conspires to get it back. He finds out that it is at Vicki's place. When Richard is there getting the letter, Vicki goes into labour and he helps with the birth.
15 October 1996
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.
22 October 1996
Joe declares his love for Caroline, which stuns her and leaves her unsure about what to do. Richard inherits a car but has to admit that he can't drive. They all decide to help him get his licence.
29 October 1996
Del stands up to his father and ends up being fired. He decides to set up his own company and convinces Caroline to join him. Richard is commissioned to paint a mural in the South Bronx but the locals don't want it.
12 November 1996
Del lies about being Jewish in order to date a woman and asks Richard for help when he goes to her place for dinner. Caroline wins a cartooning award but Joe refuses to attend because it is sponsored by a company that makes furs.
19 November 1996
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.
26 November 1996
An old friend of Richard's father, Ben, appears. Ben was a struggling stand-up comedian and they now want him for a benefit. Richard has issues with his father so Caroline intervenes to get them together.
3 December 1996
When Caroline's cat starts acting oddly, Joe recommends that it should see a cat therapist. The therapist decides that Richard is the problem as he has issues with animals. Annie goes on a blind date organised by her mother.
10 December 1996
It's Christmas time and Caroline and Richard have different approaches to it. Annie's mother moves in with her because she has separated from her husband. Charlie hires a new secretary for Del. However, he hadn't checked out her past.
17 December 1996
Del hires an unsuccessful stripper-gram girl as a receptionist and Charlie is jealous. He also tries to convince Richard to draw some Christmas cards. Caroline is accidentally locked in her building's laundry overnight with a homeless man.
7 January 1997
Caroline's romance hits a snag when Joe's ex-girlfriend turns up and wants to move into his spare bedroom. Caroline decides to let him move in with her. Richard is given a large piece of marble to sculpt and stores it at Caroline's place.
14 January 1997
Annie's sister, Donna, is a singer and is visiting. She finds Richard's letter and wants to use it as inspiration for a new song. Caroline has left her black pumps at Joe's place but she is reluctant to go to his place since the break-up.
21 January 1997
Del arranges to exhibit one of Richard's paintings at his club. A wealthy woman there takes an interest in Richard, but not for his art. She wants him to quit working for Caroline. Caroline volunteers to read to the elderly.
11 February 1997
Richard and Caroline go to an NBA basketball match but he only goes to hear the singer of the national anthem. He wins the chance to win a $100 000 basketball three point throw. Unfortunately, Richard has no idea about how to do this.
18 February 1997
Richard is trying to get his artwork reviewed by a famous artist. To help sell one of his paintings Caroline says that he is dead. When she is successful, Richard decides to tell everyone that he is dead. Then, he has to have a funeral.
25 February 1997
After blowing off Caroline a few times, Annie decides to go with her on a girls' weekend to the snow. However, as neither can ski, they have to find something else to do, which means men. Richard dates a woman he met at a bookstore.
11 March 1997
For the first time, Caroline decides to go to a restaurant to dine alone and it doesn't go well. Then she goes solo to a movie. Del tries to date Annie's friend, who is a convicted pyromaniac. Charlie sees monkeys all over the city.
1 April 1997
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.
8 April 1997
Caroline helps an elderly neighbour but the lady starts taking advantage of her. Things come to a head when she asks Caroline and Annie to help her take her naked dead husband to a funeral home.
15 April 1997
Caroline is obsessive about being liked by everyone and becomes upset when an obscure newspaper stops running her cartoon. She takes Richard on a road trip to the newspaper. Annie plots revenge on a critic who panned her performance.
22 April 1997
Caroline is having trouble getting the building superintendent to fix her shower so she hires an 'ombudsman' to intervene. Annie saves the life of a man in the audience of Cats and tries to use him to advance her career.
6 May 1997
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.
13 May 1997
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.
13 May 1997
Sofia breaks off her engagement, stays over and forces Caroline and Richard to sleep in the same bed. However, Sofia has an ulterior motive. Caroline expresses her true feelings. Annie's role in a soap opera doesn't quite go as expected.
22 September 1997
After her message of love to Richard, Caroline becomes anxious when he doesn't return her call. Then Richard stuns everybody when he announces that he has married Julia. Annie causes Del to become worried about his new girlfriend.
29 September 1997
Annie is unable to get her job back in Cats and struggles to cope with all the free time. Julia and Richard split up when he objects to the clothes she dresses him in. Richard and Charlie's work partnership is going slowly.
6 October 1997
Caroline meets a novelist at her book signing and goes out on a date with him. However, she then tries to read his book first. To make some money, Julia gets a job at Remo's. She is unused to working and it doesn't go well.
13 October 1997
It's Richard's birthday and he's upset when Julia throws a surprise birthday party for him. It becomes worse when she invites many people from his past. Unknowingly, Caroline has been stealing cable TV for three years.
20 October 1997
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.
3 November 1997
Richard's predecessor has come for a visit. She is trying to become pregnant and wants Caroline to donate an egg to her. Annie uses the occasion to mess with Richard. Del becomes nostalgic when he sees his old Porsche on the street.
10 November 1997
Annie's old music teacher is coming to town expecting to see her in Cats. She decides to crawl to her former boss to get her job back. Charlie and Richard volunteer to go on a drug trial for the money, but there are some side effects.
17 November 1997
Del comes up with a novel way to improve sales of Caroline in the City cards. Annie is romantically pursued by her piano accompanist. Richard buys a belated wedding ring for Julia but he suspects that a delivery boy stole it.
24 November 1997
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.
1 December 1997
Annie's cousin comes to town and wants to drop out of school to become an actress. Annie wants stop her. Del wants Caroline to endorse a councilman with her cartoon character but she is reluctant to enter the political arena.
8 December 1997
It's Christmas and Caroline's family is coming to her. To earn money, Richard gets a second job as a car salesman without telling Julia. He's unsuccessful at it and all he does is make everybody think that he is having an affair.
15 December 1997
It's Christmas holidays and Richard and Julia are off to Hawaii on a belated honeymoon only to be snowed in. Caroline visits the Cassidy's for Christmas dinner but it doesn't go well. Charlie's father comes to visit him.
5 January 1998
It's the start of the new year and Annie blurts out about the feelings Caroline had for Richard. Del and Charlie go a greeting card convention to sell Caroline in the City cards. They have to come up with something special.
12 January 1998
The parents of Annie's new boyfriend, Seth, run a radio quiz show. They convince Caroline to go on as a contestant. However, she has second thoughts. Annie's having trouble coming to terms with how close Seth's family is.
19 January 1998
One of Del's old girlfriends turns up and tells him that he has ten year-old daughter. However, he has a lot of difficulty knowing what to do. Annie wants Richard to appraise her brother's art so he makes the most of it.
26 January 1998
It's a busy time and Richard and Caroline are working overtime. Julia is upset at Richard's absence and tells Caroline she should walk "a mile in my shoes". In a scene reminiscent of The Outer Limits, Caroline and Julia exchange places.
2 February 1998
Trevor has left a toothbrush at Caroline's and she is worried about the implications - long term commitment. Annie is happy as her mother is finally leaving. Del and Charlie come up with a publicity stunt using a groundhog and a cape.
9 March 1998
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.
16 March 1998
Caroline's mother comes to visit and Annie can't believe how well Caroline and her mother get on together. However, this only on the surface. Richard goes on a gambling tour hoping to cash in the $100 bus voucher, and to read a book.
6 April 1998
Del and Charlie pose as a gay couple so as to get cheaper health insurance. Things get difficult when they are invited to a gay party and Del meets a beautiful woman. Richard wants to get on a jury but is having trouble getting selected.
13 April 1998
Annie new boyfriend was a priest and has never been with a woman. Del changes Caroline's cartoon without telling her but nobody thinks his change is funny. Julia's father is in town and wants to meet Richard supposedly to make up.
27 April 1998
A local deli decided to change the name of a sandwich from the Jo Anne Worley Club to the Caroline in the City Club. Jo Anne starts a very popular campaign to get it changed back. This upsets Caroline as she now feels everybody hates her.
4 May 1998
Julia wants Richard to quit working for Caroline but he has trouble doing so. Julia suggests that they go to a counsellor. After hearing their story, the counsellor insists that Richard quit and he then applies for Richard's job.
4 May 1998
Dr. Leslie is fitting in as a colourist but his former patients keep harassing him. Then Caroline and everybody else also want him to give them relationship advice, which drives him to take an extraordinary measure.
18 May 1998
Richard and Julia are heading to Europe for the holidays and throw a going away party. The party is a bore but it becomes interesting when Caroline and Annie discover Julia having an affair with an unidentified man.
18 May 1998
After Richard hears about Julia's affair with the bullfighter, he decides to fly to Spain after her. However, it all turns out to be a misunderstanding. Del's new girlfriend has a son and so he pretends to like baseball.
21 September 1998
Richard and Caroline finally realise that they love each other. However, before they manage to go to bed together there are doubts and interruptions. Then there is the news that Eagle Greeting Cards has been taken over.
28 September 1998
Caroline refuses to work in the new office Del has organised. Julia's father takes all Richard's possessions but he refuses Caroline's help. He is broke and homeless, and ends up staying in Caroline's office.
5 October 1998
It's Caroline's and Richard's first day in the office and there is a period of adjustment as they get used to all the other workers. Annie has trouble getting the romantic eye of her physical trainer.
12 October 1998
Caroline is wary about attending a focus group on Caroline in the City cards and with good reason. Annie is fired from Cats and is then dropped by her agent. Annie's dry cleaner keeps asking her out and she finally accepts.
26 October 1998
It's Halloween and Del is put in charge of the firm's Halloween party, only to find out that it is a sure-fire way to be sacked. Caroline and Richard go on their first date together but they have different ideas about what they should do.
2 November 1998
Del wants to produce an animation on female sexuality. When Caroline finds Richard's divorce papers, her curiosity about their content causes problems when they are misplaced. Then she finds out that Richard is still married.
9 November 1998
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.
16 November 1998
Now that Caroline and Richard are together, Annie feels on the outer. It ends up with all three going to a concert together, which doesn't end well. Del has to tread a diplomatic line when asked to do something that he doesn't want to.
30 November 1998
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.
14 December 1998
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.
21 December 1998
It'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.
11 January 1999
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.
18 January 1999
Caroline mentors a young teenager for a week. Things become complicated when he gets a crush on her. Del also has a teenage assistant but uses him to pick up his mother. Richard becomes determined to sell one of his paintings.
25 January 1999
Richard gets Annie a job as a model for a cartoonist but the work doesn't quite live up to expectations. Charlie is bored with his special assignment at work and he becomes concerned about having a purpose for his life.
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.
15 March 1999
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.
8 March 1999
There is big party to celebrate Caroline's 2000th cartoon strip. However, Caroline has a mental block and is unable to draw anything. Her friends give her plenty of bad suggestions, so she contemplates retirement and trying something else.
22 March 1999
Caroline has to make a quick return home. Her parents have moved house but her grandmother is staying put and doesn't want to move out. This leaves Richard in charge of a sick Annie and a depressed Del, and having to make a speech.
29 March 1999
An old friend of Caroline from Peshtigo drops in, but does Caroline have feelings for him? After the death of an artist, Richard is given the opportunity to replace him at an exhibition, as long as he makes his paintings more depressing.
5 April 1999
With feelings for Randy, Caroline is confused about her relationship with Richard and wonders where it is heading. Richard is involved in a robbery at the video store and is locked in a storeroom, where he reflects on his relationship.
26 April 1999
Caroline accepts Richards marriage proposal. However, they have very different ideas about how the wedding will go. Richard drops a bombshell when he reveals that he has a son from his brief marriage to Julia. They decide to go to Italy.
26 April 1999
Richard needs to be closer to his son and wants to go 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 hots up.
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