Caroline in the City - Season 1 (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.

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 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.

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.

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.

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.

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.

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.

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.

Caroline returns to home her town of Peshtigo, Wisconsin 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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.