Three months after Caroline had pulled out of her wedding, Richard is in France painting. He is unsuccessful, returns home and starts work in an ice cream parlour. When Salty is injured, Caroline ends up dating the much younger vet.
Richard finds out that Caroline didn't read the letter he left her so he conspires to get it back. He finds out that it is at Vicki's place. When Richard is there getting the letter, Vicki goes into labour and he helps with the birth.
Del stands up to his father and ends up being fired. He decides to set up his own company and convinces Caroline to join him. Richard is commissioned to paint a mural in the South Bronx but the locals don't want it.
Del lies about being Jewish in order to date a woman and asks Richard for help when he goes to her place for dinner. Caroline wins a cartooning award but Joe refuses to attend because it is sponsored by a company that makes furs.
Annie wants to be Julie Andrew's understudy in Victor/Victoria and 'kidnaps' her in order to get an audition. She then practises being a man to get the part. Richard very reluctantly has to go hospital to get a polyp removed.
An old friend of Richard's father, Ben, appears. Ben was a struggling stand-up comedian and they now want him for a benefit. Richard has issues with his father so Caroline intervenes to get them together.
When Caroline's cat starts acting oddly, Joe recommends that it should see a cat therapist. The therapist decides that Richard is the problem as he has issues with animals. Annie goes on a blind date organised by her mother.
It's Christmas time and Caroline and Richard have different approaches to it. Annie's mother moves in with her because she has separated from her husband. Charlie hires a new secretary for Del. However, he hadn't checked out her past.
Del hires an unsuccessful stripper-gram girl as a receptionist and Charlie is jealous. He also tries to convince Richard to draw some Christmas cards. Caroline is accidentally locked in her building's laundry overnight with a homeless man.
Caroline's romance hits a snag when Joe's ex-girlfriend turns up and wants to move into his spare bedroom. Caroline decides to let him move in with her. Richard is given a large piece of marble to sculpt and stores it at Caroline's place.
Annie's sister, Donna, is a singer and is visiting. She finds Richard's letter and wants to use it as inspiration for a new song. Caroline has left her black pumps at Joe's place but she is reluctant to go to his place since the break-up.
Del arranges to exhibit one of Richard's paintings at his club. A wealthy woman there takes an interest in Richard, but not for his art. She wants him to quit working for Caroline. Caroline volunteers to read to the elderly.
Richard and Caroline go to an NBA basketball match but he only goes to hear the singer of the national anthem. He wins the chance to win a $100 000 basketball three point throw. Unfortunately, Richard has no idea about how to do this.
Richard is trying to get his artwork reviewed by a famous artist. To help sell one of his paintings Caroline says that he is dead. When she is successful, Richard decides to tell everyone that he is dead. Then, he has to have a funeral.
After blowing off Caroline a few times, Annie decides to go with her on a girls' weekend to the snow. However, as neither can ski, they have to find something else to do, which means men. Richard dates a woman he met at a bookstore.
For the first time, Caroline decides to go to a restaurant to dine alone and it doesn't go well. Then she goes solo to a movie. Del tries to date Annie's friend, who is a convicted pyromaniac. Charlie sees monkeys all over the city.
Annie's mother is driving her crazy. Caroline finds out that some stores are no longer stocking her cards. Del works out a plan and takes the store owner out for a dinner with Caroline, but he misinterprets what she is offering.
Caroline is obsessive about being liked by everyone and becomes upset when an obscure newspaper stops running her cartoon. She takes Richard on a road trip to the newspaper. Annie plots revenge on a critic who panned her performance.
Caroline is having trouble getting the building superintendent to fix her shower so she hires an 'ombudsman' to intervene. Annie saves the life of a man in the audience of Cats and tries to use him to advance her career.
Caroline is to appear on The Tonight Show to publicise her new book. She accidentally takes some drugs before going on. Talk of who Richard's father is means Charlie goes looking for his. Del tries to give Richard some dating tips.
Julia, Richard's old girlfriend, has returned with the news that she is getting married. He tries to impress her by asking Caroline to act as his wife. Then it becomes a game of oneupmanship between Julia and Richard.
Sofia breaks off her engagement, stays over and forces Caroline and Richard to sleep in the same bed. However, Sofia has an ulterior motive. Caroline expresses her true feelings. Annie's role in a soap opera doesn't quite go as expected.