After her message of love to Richard, Caroline becomes anxious when he doesn't return her call. Then Richard stuns everybody when he announces that he has married Julia. Annie causes Del to become worried about his new girlfriend.
Annie is unable to get her job back in Cats and struggles to cope with all the free time. Julia and Richard split up when he objects to the clothes she dresses him in. Richard and Charlie's work partnership is going slowly.
Caroline meets a novelist at her book signing and goes out on a date with him. However, she then tries to read his book first. To make some money, Julia gets a job at Remo's. She is unused to working and it doesn't go well.
It's Richard's birthday and he's upset when Julia throws a surprise birthday party for him. It becomes worse when she invites many people from his past. Unknowingly, Caroline has been stealing cable TV for three years.
Annie is going to her 10 year high school reunion intent on revenge. When her date falls through she goes with Del, complete with an elaborate story. Julia sets up Caroline on a blind date but she doesn't want to go, until she sees him.
Richard's predecessor has come for a visit. She is trying to become pregnant and wants Caroline to donate an egg to her. Annie uses the occasion to mess with Richard. Del becomes nostalgic when he sees his old Porsche on the street.
Annie's old music teacher is coming to town expecting to see her in Cats. She decides to crawl to her former boss to get her job back. Charlie and Richard volunteer to go on a drug trial for the money, but there are some side effects.
Del comes up with a novel way to improve sales of Caroline in the City cards. Annie is romantically pursued by her piano accompanist. Richard buys a belated wedding ring for Julia but he suspects that a delivery boy stole it.
When cleaning up his apartment, it comes out that Richard is a music composer. He was taught by Marvin Hamlisch and it appears that Marvin stole one of Richard's tunes. Caroline meets an old boyfriend, but then there is the dog.
Annie's cousin comes to town and wants to drop out of school to become an actress. Annie wants stop her. Del wants Caroline to endorse a councilman with her cartoon character but she is reluctant to enter the political arena.
It's Christmas and Caroline's family is coming to her. To earn money, Richard gets a second job as a car salesman without telling Julia. He's unsuccessful at it and all he does is make everybody think that he is having an affair.
It's Christmas holidays and Richard and Julia are off to Hawaii on a belated honeymoon only to be snowed in. Caroline visits the Cassidy's for Christmas dinner but it doesn't go well. Charlie's father comes to visit him.
It's the start of the new year and Annie blurts out about the feelings Caroline had for Richard. Del and Charlie go a greeting card convention to sell Caroline in the City cards. They have to come up with something special.
The parents of Annie's new boyfriend, Seth, run a radio quiz show. They convince Caroline to go on as a contestant. However, she has second thoughts. Annie's having trouble coming to terms with how close Seth's family is.
One of Del's old girlfriends turns up and tells him that he has ten year-old daughter. However, he has a lot of difficulty knowing what to do. Annie wants Richard to appraise her brother's art so he makes the most of it.
It's a busy time and Richard and Caroline are working overtime. Julia is upset at Richard's absence and tells Caroline she should walk "a mile in my shoes". In a scene reminiscent of The Outer Limits, Caroline and Julia exchange places.
Trevor has left a toothbrush at Caroline's and she is worried about the implications - long term commitment. Annie is happy as her mother is finally leaving. Del and Charlie come up with a publicity stunt using a groundhog and a cape.
Del decides to sell celebrity hair when Annie gets a hairdressing appointment at a celebrity hairdressers. Caroline reports a rude cabbie but Richard fails to turn up as a witness when he becomes addicted to a computer bulletin board.
Caroline's mother comes to visit and Annie can't believe how well Caroline and her mother get on together. However, this only on the surface. Richard goes on a gambling tour hoping to cash in the $100 bus voucher, and to read a book.
Del and Charlie pose as a gay couple so as to get cheaper health insurance. Things get difficult when they are invited to a gay party and Del meets a beautiful woman. Richard wants to get on a jury but is having trouble getting selected.
Annie new boyfriend was a priest and has never been with a woman. Del changes Caroline's cartoon without telling her but nobody thinks his change is funny. Julia's father is in town and wants to meet Richard supposedly to make up.
A local deli decided to change the name of a sandwich from the Jo Anne Worley Club to the Caroline in the City Club. Jo Anne starts a very popular campaign to get it changed back. This upsets Caroline as she now feels everybody hates her.
Julia wants Richard to quit working for Caroline but he has trouble doing so. Julia suggests that they go to a counsellor. After hearing their story, the counsellor insists that Richard quit and he then applies for Richard's job.
Dr. Leslie is fitting in as a colourist but his former patients keep harassing him. Then Caroline and everybody else also want him to give them relationship advice, which drives him to take an extraordinary measure.
Richard and Julia are heading to Europe for the holidays and throw a going away party. The party is a bore but it becomes interesting when Caroline and Annie discover Julia having an affair with an unidentified man.
After Richard hears about Julia's affair with the bullfighter, he decides to fly to Spain after her. However, it all turns out to be a misunderstanding. Del's new girlfriend has a son and so he pretends to like baseball.