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.
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.
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 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.
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.
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.
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.
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.
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 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.
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.
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.
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.
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.