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.
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.