
Caroline in the City
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.
- Metascore65
- 1995-1999
- 4 seasons
- CBS Media Ventures
- Comedy, Drama
- 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.
Season 1 Episode Guide
24 Episodes 1995 - 1996
Episode 1
Pilot
Thu, Sep 21, 1995 23 mins
Caroline has been advertising for a colourist to finish off her cartoons and is disappointed with the candidates until Richard arrives. He is bad tempered and sarcastic but he gets the job. Caroline had just broken up with Del who works for her publisher and manages the Caroline in the City comic strip products. He already has already moved on with a new date and, in desperation for some oneupmanship, Caroline chooses a new date by throwing fruit out of the window. He doesn't turn up but Richard saves the day by going as her date.
Episode 2
Caroline and the Mugger
Thu, Sep 28, 1995 22 mins
Del and Caroline are supposed to be going to Atlantic City for the weekend. However, work deadlines prevent from her from going. Richard is mugged on his way to work and Caroline tries to help Richard overcome the psychological effects of the mugging. She helps him by buying him a new wallet. On the trip home, they meet the mugger on the subway and have him arrested. It turns out that Richard had exaggerated the size of the mugger and he is having trouble coming to terms with the fact that he is a bit of wimp.

Episode 3
Caroline and the Gay Art Show
Thu, Oct 5, 1995 22 mins
Caroline and Annie are determined to get Richard's art work displayed at an art gallery and put on a performance to get noticed. Richard takes his work to be displayed and is accepted for a show. When deciding which painting to display, Richard finds out that the gallery only shows work by gay artists. Richard was going to stop the display of his work until he finds out that he could get $20 000 if it sold.

Episode 4
Caroline and the Bad Back
Thu, Oct 12, 1995 21 mins
Caroline and Del are very competitive playing racquetball. However, Caroline seriously injures her back and will have difficulty meeting the deadline for her next cartoon. Richards is not exactly sympathetic. Hearing that the newspapers are going to use one of her competitors' cartoons instead makes her very determined. She takes some of Annie's powerful pain killers and knocks herself out. Del and Richard collaborate to finish the cartoon.

Episode 5
Caroline and the ATM
Thu, Oct 19, 1995 22 mins
Caroline is taking money out of the ATM when Annie points out that she has something in her nose. So Caroline picks her nose. The ATM malfunctions and she doesn't receive the money so she meets the bank operations manager. When she finds out that there is a camera in the ATM she initially decides to not go after the money out of embarrassment. However, she changes her mind and eventually gets her money, although not without some discomfit. Richard is finding his girlfriend Shelly irritating so he breaks it off by claiming he is allergic to her dog. However, when she gives away the dog he is in trouble.

Episode 6
Caroline and the Folks
Thu, Nov 2, 1995 22 mins
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.

Episode 7
Caroline and the Opera
Thu, Nov 9, 1995 22 mins
Caroline's auntie, Mary, arrives for a visit. She brings Caroline up to date with the news and some embarrassing stories of Caroline's childhood. Mary also sets her up with a date Caroline knew from her home town, Peter. Caroline wants Del to go to the opera but, as he doesn't want to go, she takes Peter instead. This makes Del very jealous and he resorts to asking Richard for help, which leads to some extreme actions.

Episode 8
Caroline and the Balloon
Thu, Nov 16, 1995 21 mins
Caroline has a large 'Caroline in the City' balloon in the Thanksgiving Day parade and needs some people to hold the rope and pull the balloon along. Richard is a reluctant starter but it was either the balloon or Shelly. Then Shelly takes an anti-fur stance that eventually results in the balloon being released. This causes a number of problems that included injuring Florence Henderson. Caroline is very upset when the balloon is eventually destroyed.
Episode 9
Caroline and the Convict
Thu, Dec 7, 1995 21 mins
Annie is very excited about her new boyfriend Stephen, even getting a tattoo with him. They all have dinner together when he admits he was in prison. That night, whilst Caroline is asleep, her apartment is broken into. Caroline's suspicions are that Stephen sneaked in during the night from Annie's apartment but Annie is upset with Caroline for thinking this way. They set a trap to find out.

Episode 10
Caroline and the Christmas Break
Thu, Dec 14, 1995 22 mins
It's Christmas time and Caroline is spreading Christmas cheer. Caroline and Del are trying to go for a holiday break but everything is booked. However, he makes an inappropriate comment, upsets Caroline and then wants to break up with her. Richard is still having trouble breaking up with Shelly so they conceive of a plan. They want Charlie to take her out and, hopefully, off Richard's hands. Of course, things don't go as planned.
Episode 11
Caroline and the Gift
Thu, Jan 4, 1996 22 mins
It's the new year and Richard has started a second job painting portraits. His first client wants to be painted naked, which leads to a misunderstanding. At the New Year's eve party Annie makes a date with a man. However, she can remember his name but cannot remember what he looks like or anything about him. Caroline tries to return earrings that Del had bought her for Christmas but is astonished when she finds out how much they are worth. This also leaves her with a dilemma.

Episode 12
Caroline and the Married Man
Thu, Jan 11, 1996 21 mins
Richard is one of three artists who could receive an arts council grant to paint a mural. The man who makes the decision, Tom, is very interested with Caroline. Richard, thinking it will help with the grant, sets him up with her. Caroline and Tim get on well together and she goes out him without any prompting from Richard. However, there is a fly in the ointment that leaves Richard with an ethical dilemma.

Episode 13
Caroline and the Twenty-Eight-Pound Walleye
Thu, Jan 25, 1996 22 mins
Caroline's home town of Peshtigo, Wisonsin decides to dedicate a park to her. As Richard is the only person available, he accompanies her back to Peshtigo. Caroline's brother, who is a surgeon, also returns home and there is some intense sibling rivalry. Even the dedication doesn't go well. Annie gives her role to her understudy so that she can dance in front of her parents. But Annie has second thoughts when she thinks the understudy is after her position in the 'Cats' chorus line.

Episode 14
Caroline and the Watch
Thu, Feb 1, 1996 22 mins
Caroline buys an old desk that will allow both Caroline and Richard to work at the same time. However, it is too big to fit through the door and so Caroline is working in the hallway. A watch found in a locked drawer with a mysterious engraving sends Caroline off to find the original owner and the secret of the watch. One of Del's employees dies and he goes to the funeral only to find out some unpleasant facts about him. Annie is studying Caroline's cat, Salty, to learn some new moves for her dancing.

Episode 15
Caroline and the Bad Date
Thu, Feb 15, 1996 22 mins
Del has a date with a model and needs a man to go with him as a blind date for her friend. So, who would he ask but Richard? Unfortunately, the models find something better to do and don't turn up. Del sees an old date in the restaurant that is interested in Richard. Annie gives Caroline lessons about men by observing what they buy in a men's clothes store. Caroline eventually picks up a man but the date doesn't go well as he has an endless list of paranoia and phobias. She ends up taking him to hospital.

Episode 16
Caroline and the Proposal
Thu, Feb 22, 1996 22 mins
After the last episode's bad dates, Del proposes to Caroline. She is unsure what to do and Richard is no help as he has a crush on her. As a result he decides to find a new job. The employment counsellor, Maddie, is going through a bitter marriage break-up and seduces Richard. Annie opens Caroline's eyes to Richard's feelings and so Caroline goes around to his place only to find him with Maddie. This changes everything.

Episode 17
Caroline and the Kid
Thu, Mar 14, 1996 22 mins
One of Caroline's old boyfriends from Italy, Marco, turns up in New York. Del has trouble coping with it and there begins a game of one-upmanship. For charity, Caroline offered to paint a Caroline mural. The winning bid requires it to be painted on the wall of a self-indulgent 10 year-old boy who didn't want it anyway. When the housekeeper suddenly quits, Caroline and Richard have to remain to look after him.

Episode 18
Caroline and the Ex-Wife
Thu, Mar 28, 1996 22 mins
Caroline is feeling that her relationship with Del is in a bit of a rut. To add a bit of spontaneity Del suggests that they go up to his cabin in Vermont, something Caroline didn't know existed. It turns out that one of his former wives is using it with her boyfriend. He happens to be a health fanatic and he also makes a pass at Caroline. Richard has a broken light switch and is having trouble getting the building superintendent to fix it. So he employs one of Annie's brothers to fix it. The brother decides to quit the family's funeral business, which causes a family upheaval.

Episode 19
Caroline and the Movie
Thu, Apr 4, 1996 21 mins
Del's car is impounded and he has difficulties getting it out of the impound yard because it was given to somebody else. John Landis is shooting a movie in the street outside Caroline's apartment. Caroline volunteers herself along with Annie and Richard to be extras in a street scene. Annie is very excited to see Robby Benson in person and continues to ruin each take until she is sacked. Caroline has to kiss somebody so Richard manipulates the scene so that it is him. However, he has trouble kissing Caroline.

Episode 20
Caroline and the Cereal
Thu, Apr 18, 1996 22 mins
Caroline and her agent have a meeting and he informs her that they want to start a new cereal with her Caroline cartoon picture on the box. Caroline is concerned that the cereal should be healthy and she is given a box to try. Richard notices that the cereal looks like an intimate part of the female body, which upsets Caroline. Del wants to learn to dance for his wedding with Caroline and asks Annie to teach him.

Episode 21
Caroline and Richard's Mom
Thu, Apr 25, 1996 22 mins
Richard's mother comes for a visit. She then tells Caroline that she can bring her to the big man at NBC, Warren Littlefield and get him to make a cartoon show of her cartoon. But Richard tells her not to expect much because she once told him that she would show his artwork to Salvador Dali and he never got any feedback. And when she fails to deliver, Richard tells her off. Del whom Caroline told to go get a pedicure but didn't want to cause he thought it's not masculine, gets hooked on all the treatments.

Episode 22
Caroline and the Bridesmaids
Thu, May 9, 1996 22 mins
The wedding preparations are proceeding but it is not all going smoothly. Caroline is having trouble with the bridesmaids, especially Annie. Her casual approach to life means that jobs are not being done on time. Eventually, the pressure gets to her and she quits. Del also has to continually rearrange his attendants and is having considerable difficulty finding suitable men.

Episode 23
Caroline and the Wedding
Thu, May 16, 1996 22 mins
With the wedding only days away, preparations are speeding up. There is a new priest they haven't met and Caroline is having some small doubts. Richard writes a love letter to Caroline and puts it in her apartment. Circumstances prevail that she mean she doesn't receive it and Richard unsuccessfully tries to get it back. He then leaves suddenly without leaving any reason but the letter remains hidden.

Episode 24
Caroline and the Condom
Mon, Aug 5, 1996 21 mins
Caroline has writer's block so this episode has Richard and Caroline looking back on some of the events Season 1, from the time when Richard was first employed. The central story is about the time Del and Caroline agree to try abstinence, or 'dessert' as she calls it. However, she weakens and goes to buy some condoms. Circumstances mean that she tries to shop lift them but is caught.
