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.
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.
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.
Caroline and Joe are getting on and Del is envious. Annie is audited by the IRS. When the auditor finds out she is in Cats he offers to go easy on her if Annie gets him an audition for Cats.
Joe declares his love for Caroline, which stuns her and leaves her unsure about what to do. Richard inherits a car but has to admit that he can't drive. They all decide to help him get his licence.
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.