Caroline in the City

Richard and Caroline finally realize 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.

Caroline refuses to work in the new office Del has organized. 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.

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.

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.

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.

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.

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.

Now that Caroline and Richard are together, Annie feels on the outside. 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.

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

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.

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.

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.

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.

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.

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.

Caroline and Richard travel to her parents' home for their 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's plans to rent out her house in Wisconsin hit an unexpected snag when Grandma Duffy 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. Meanwhile, Richard has his hands full in New York when he agrees to take Caroline's place by caring for Annie (who is sick) and Del (who thinks his girlfriend may be cheating on him).

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. Meanwhile, Richard gets his first real break as an artist when an eccentric gallery owner offers to exhibit his work -- but only if he can create another 'bleak' painting in time for the next day's show.

Caroline gives Richard a matrimonial ultimatum; but on his way to propose to her, he is taken hostage in a video store holdup. He decides that escape will prove his manhood and worthiness of Caroline -- and when he is wheeled in by paramedics, he does indeed propose.

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.

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: he never wanted to have children. But when he arrives alone in Italy, Richard discovers that Julia has abandoned the baby, and slowly becomes a model father. Meanwhile, Annie and Del begin a clandestine relationship. Flashing forward six months later, the series finale finds Caroline headed to the altar with Randy, when an unexpected guest arrives during the wedding ceremony: Richard, holding his infant son...