Caroline in the City

Caroline hires Richard as the new colorist for her comic strip. Annie tries throwing fruit out Caroline's window to hit a date for Caroline.

Richard has to tell Caroline that he's been mugged. The mugger also took Caroline's drawings that are due the next day, forcing them to rush new ones and Caroline cancelling a date with Del.

Caroline and Annie convince a gallery owner they meet at Remo's to look at Richard's paintings. The owner agrees to show Richard's work. Unknown to Richard, it's a gallery for gay artists.

When Caroline gets her back injured, and Annie gives her some "better" painkillers than the doctors, Del and Richard rush to create a Caroline in the City cartoon strip so that Caroline doesn't miss her deadline and a Cathy strip replaces it.

In order to claim money she did not receive while making an ATM withdrawal, the bank manager must watch a video of Caroline making the withdrawal. This sends Caroline into a panic as, unaware she was being recorded, she picked her nose.

Del gets delayed when he and Caroline are to meet Del's parents at Remo's, leaving Caroline to her own devices. Annie disrupts Richard's plan to do nothing for his 30th birthday.

When Del tries to get out of going to the opera with Caroline, she goes with an old high school classmate who happens to be richa and successful.

Caroline's cartoon character gets a balloon in the Thanksgiving Day parade. It gets set loose, in the process hurting Florence Henderson who is the parade marshal.

When Caroline's apartment is burglarized, Caroline suspects Annie's new boyfriend, recently released from prison.

Annie attempts to help Richard end things with Shelly, while Del and Caroline reconsider their relationship when vacation plans bring up issues.

Having recently split up, Caroline is unsure what to do when Del gives her a gift that she thinks is very expensive. Meanwhile Richard is commissioned to do a nude portrait of a woman who turns out to have ties with the mob.

Caroline gets set up by Richard on a date with a man who could get Richard a well-paying mural job. But Richard later discovers the man is married.

Caroline's hometown has a ceremony in her honor. Caroline arrives along with Richard to find things haven't changed much, as her brother continues to upstage her at every turn. Annie thinks her understudy is trying to steal her place in Cats.

Caroline buys a new work desk that is difficult to get into the apartment. She finds an old watch in a stuck drawer and looks for the original owners whose names are on the inscription. Del goes to the funeral of an employee that Charlie tells him was embezzling from him.

Caroline meets a man who turns out to be overly paranoid. Del sets himself and Richard up on a double date with two models.

Richard learns that Del proposed to Caroline. Thinking he'll just be in the way, Richard starts looking for a new job. Annie and Remo try to convince Caroline that she's oblivious of Richard's feelings for her.

Del feels inadequate when he meets a particularly chiseled ex-boyfriend of Caroline's. Caroline and Richard are hired to paint a mural in the room of a spoiled little boy.

Del and Caroline go on a vacation to Del's cabin, only to find his ex-wife staying there with her latest partner. Annie has family troubles when Richard convinces her brother to quit the family business.

Caroline, Richard, and Annie are extras in a movie filming outside their building. Del's Porsche gets towed, only for someone else to pick the car up as theirs.

Caroline's cartoon character is offered to be on a cereal box, but Caroline can't get past the shape of the cereal looking too much like a female body part. Del asks Annie to teach him how to dance.

Richard's mother makes a surprise visit, continuing a string of claims that she knows all kinds of well-known people and irritating Richard in front of Caroline.

Caroline doesn't feel like Annie is taking her position as maid of honor seriously. Del is having difficulty finding ushers for the wedding.

The wedding is threatened by dreams of Richard, a last-minute change to an inexperienced priest, and more.

Caroline has flashbacks of Richard's first day working with her. (This episode was aired outside of the normal season airings, and out of order. It makes more sense viewed just after episode 14, "Caroline and the Watch".)

Caroline starts dating her cat Salty's vet. Richard fails at being an artist in France and returns to New York.

Richard goes out of his way to recover the letter he left for Caroline before she sees it.

Annie gets audited by a man who is an extreme Cats fanatic. Richard has overly-amourous neighbors that keep him awake all night. Caroline isn't sure what to do when Joe says he finds it weird that she's still friends with her ex Del.

Caroline freaks out when Joe says "I love you" way too soon. Richard inherits a car but doesn't know how to drive.

Del stands up to his father who owns the greeting card company, resulting in Del being fired. Del decides to start his own greeting card business and tries to coerce Caroline to be one of his first clients. Richard is hired to paint a mural in a seedier area of the city.

Del pretends to be Jewish to date a woman who will only date Jewish men. Joe refuses to go to an award show where Caroline won an award because one of the sponsors uses animal products.

Annie dresses up as a man for an audition. Richard needs surgery and gets nervous before the operation.

Richard's father asks for his son's help in reviving an old comedy routine.

Joe recommends a therapist for Salty, Caroline's cat. The cat therapist in turn says Salty's problems are due to Richard.

Annie's parents split up and her mother suddenly moves in with her. Richard takes a temporary holiday job. Charlie and Del think their new assistant is a deranged killer.

Del tries to get Richard to draw some greeting cards based on a porcupine doodle, but Richard fears it would be selling out as an artist. Caroline gets locked in the laundry room overnight with a bum.

Richard gets a huge piece of marble to chisel his own art, which he does in Caroline's living room. Joe's ex-girlfriend returns from traveling, and Caroline discovers they still live together.

Annie's sister Donna visits, looking to revive her singing career. She stumbles on the letter that Richard wrote to Caroline that Annie still has, and turns it into a song to Richard's dismay. Del and Charlie get snowed in inside Del's porsche.

In a scheme to date a woman, Del agrees to have one of Richard's painting hung at his club. Richard isn't impressed when he sees where.

Caroline drags Richard to a Knicks basketball game, where his seat is selected for a chance to win $100,000 by making a free throw shot.

Learning artists sell more after they die, Caroline inadvertently forces Richard to fake his own death to sell some artwork.

Annie and Caroline go on a trip together with an agreement to not allow men to get between them. Richard has a date with a philosophy student that he thinks he's connecting with, but Charlie and Del unintentionally interfere.

Charlie keeps seeing monkeys outside everywhere. Caroline attempts to learn to go out alone. Del dates Annie's friend, who happens to be a pyromaniac.

Del asks Caroline to come along as the artist talent when he tries to steal one of his father's clients. The client thinks Caroline is there for other reasons. Annie has problems with Richard's relationship with her mother.

Caroline helps an elderly neighbor but the lady starts taking advantage of her. Things come to a head when she asks Caroline and Annie to help her take her naked dead husband to a funeral home. Richard tries to sell his car.

Caroline takes Richard with her to find out why a small newspaper dropped her strip. Annie plots revenge on a theater critic who poorly reviewed her, getting Del and Charlie involved.

Caroline inadvertently hires someone to "talk to" her building supervisor when her shower is broken for over a week. Annie's manager is hoping to get some publicity when Annie saves a man's life, but the man isn't willing to go along with it.

Caroline is to appear on The Tonight Show With Jay Leno, but things don't go well when she discovers she may have accidentally been in contact with LSD. Del tries to teach Richard how to pick up women, and Richard ends up trying with what turns out to be the past love of his life.

Richard's long-lost love Julia is getting married in two days. Unsure how to react, Richard pretends he is married already to Caroline. Del is going bankrupt as his greeting card business isn't as successful as he'd hoped. Annie gets a part in a pilot for a new TV show.

Julia comes to Caroline's apartment in tears, still believing she and Richard are married, telling them both that her engagement is off. Annie has problems with her character as she films the show's pilot episode.

Caroline anxiously awaits Richard's response to the message she left on his answering machine---and then is stunned by what he has to say.

Caroline's already giving individual advice to the newlyweds after their first disagreement; Del tries to land a big account.

Caroline has a date with a novelist, but has to pay Richard to explain the guy's book to her. Meanwhile, Julia gets a job as a waitress.

Richard is upset because his ex-therapist wants to date Annie; Caroline finds out she's been providing free cable to the entire building.

Julia tries to help Caroline take her eyes off Richard by setting her up on a blind date. Meanwhile, Annie attends her high-school reunion.

Caroline's former colorist returns to New York and asks her to be an egg donor. Meanwhile, Del misses his Porsche and finds out that it's now owned by an escort service.

Annie tries to claw her way back into "Cats" for one night to impress her mentor, who's in town.

Richard shows Caroline a family ring that he was planning to give to Julia, and soon after, the heirloom disappears.

Richard confronts his former piano teacher, who he believes is guilty of plagiarism; and Caroline starts dating the owner of a possessive dog.

Del urges Caroline to endorse a councilman who publicly mentions her cartoon; and Richard regrets selling his first painting to the guy.

Richard takes a second job---as a used-car salesman; Annie and Caroline wonder if the colorist is cheating on Julia.

Caroline spends Christmas with Del and his family after a snowstorm leaves her parents stranded in Wisconsin; Charlie and his dad share their first holiday together.

Richard and Caroline reveal their past feelings to each other, but agree they've both "moved on"; Del recruits Annie and Charlie to help him upstage his brother.

Trivia wiz Caroline struggles to overcome her stage fright after she agrees to appear on a live radio quiz program that's broadcast nationally.

Del hears some shocking news from a former fling who's in town for the weekend; and Richard evaluates Annie's brother's work as a painter.

In an episode that pays homage to "The Outer Limits," Julia and Caroline switch identities, leaving "Julia" bewildered---about her husband's intentions for the evening.

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.

Computer-phobic Richard becomes addicted to being on-line at a cyber cafe; Caroline files a complaint against a rude cabbie; and Del ruins Annie's appointment with a famous hair stylist.

Caroline is shocked when her mom expresses her real feelings about the comic strip. Meanwhile, Del and Charlie go to Atlantic City.

For insurance purposes, Del and Charlie pretend to be gay, then Del meets a beautiful woman at a party. Meanwhile, Richard reluctantly agrees to change his appearance.

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 gets her inheritance and urges Richard to quit his job to paint full-time, but, sensing his reluctance to leave Caroline, she hires a marriage counselor.

Caroline suggests that she and Trevor move in together. Garry Shandling has a cameo as one of the therapist's other patients.

Caroline thinks that Julia has been unfaithful, and she inadvertently tells Richard, who goes to Spain, where his wife is spending the summer.

After Caroline learns the truth about Julia, Richard makes a big announcement.

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.

It's Caroline's and Richard's first day in the office and there is a period of adjustment as they get used to all the other workers. Annie has trouble getting the romantic eye of her physical trainer.

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.

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.

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 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.

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 to 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 heats up.