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 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.