Caroline in the City Season 1 - Caroline in the City Fansite

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Caroline in the City Season 1 summary

Caroline Duffy, a successful cartonist living in New York seeks a new colorist and her choice is Richard Karinsky, a uptight artist that always wears black clothes. She has ups and downs with her boyfriend Del Cassidy, who works as her editor in his fathers greeting cards company. Her neighbour and closest friend is Annie Spadaro, dancer in "Cats" who is... friendly... very friendly to men.

During the first season we get to know Caroline and her Midwest cheerful style clashes with Richard's depressing way of life. After few break-ups Del finally decides to propose to Caroline and in the same time Richard realizes that he is in love with Caroline.

Pilot Episode

Caroline splits up with her boyfriend, greeting cards company executive, Del and is infuriated to learn that not only does he have a date so soon after the break-up, but that he plans to bring along his date to their restaurant called Remo's. In desperation, Caroline announces that she has a date too the same night at the same restaurant. When her attempts to find a date on such short notice proves fruitless, she enlists the help of Richard Karinsky: her new assistant - to save the day. (more)

Pilot Episode - Caroline in the City Season 1

Caroline And The Bad Back

When Caroline and Del get carried away competing on the racquetball court, Caroline injures her back and ends up confined to bed. Meanwhile, Del and Richard work together to complete Caroline's unfinished cartoon strip to meet her rapidly approaching deadline and - to their surprise - the two polar opposites find common ground. (more)

Guest stars: David Hyde Pierce as Dr. Niles Crane, Jane Leeves as Daphne Moon,

Caroline And The Bad Back - Caroline in the City Season 1

Caroline And The Mugger

Caroline and Del are moments away from departing for a weekend trip to Atlantic City when Richard turns up at the apartment with news that he has been mugged, losing not just his wallet but his portfolio containing Caroline's drawings as well. Realising that she must stay behind to recreate her cartoons, Caroline encourages Del to go on the trip without her. Meanwhile, Caroline offers advice to help Richard deal with the trauma of being a crime victim but ends up getting him into more trouble than she'd originally thought. (more)

Guest stars: Christopher Maleki as Chris,

Caroline And The Mugger - Caroline in the City Season 1

Caroline And The Condom

Caroline decides that if she and Del resume dating then they should abstain from sex for a fortnight and instead focus on what's at the heart of their relationship. But just as when it looks like they'll weaken within a week, she's driven to a desperate act that could ruin her reputation and land her in jail. Also, working in Caroline's loft creates conflict for Richard over the boundary between his and Caroline's personal space. (more)

Caroline And The Condom - Caroline in the City Season 1

Caroline And The Convict

When Caroline and Del agree to go dinner with Annie and her new boyfriend, Warren, they realise that Annie left out one minor detail about his background - Warren is an ex-convict with criminal record. Later on, when Caroline's apartment is robbed she is faced with telling Annie that she suspects Warren was behind it, and the two friends are at longer heads with each other. Meanwhile, Caroline encourages Richard to bring something from home to personalise his workspace but soon afterwards has second thoughts when he brings in a hideous painting. (more)

Guest stars: Tim Conlon as Stephen, David Byrd as Officer Bloch,

Caroline And The Convict - Caroline in the City Season 1

Caroline and The Gay Art Show

Caroline and Annie's plan to get Richard's paintings displayed in a prestigious galley and alas, he is thrilled when their efforts earn him the recognition of gallery owner, Kenneth Arabian - until he learns that Arabian showcases art produced exclusively by gay artists. At the opening, Richard has to decide on whether he should lie about his sexuality, or confess that he is straight and risk losing the sale of his paintings. Del learns some lessons in diversity. (more)

Guest stars: Dan Butler as Kenneth Arabian, Jack Kenny as Howard Berman, Neal Lerner as Allen, Caroline's Hairdresser,

Caroline and The Gay Art Show - Caroline in the City Season 1

Caroline and The Folks

Caroline is dreading the prospect of meeting Del's parents for the first time and her nerves are further frayed when she mistakes the wrong woman for Del's mother. Meanwhile, Annie and Caroline plan to make Richard's 30th birthday exciting, although he for one has other ideas; rather he chooses to spend a quiet evening at home watching his favourite video. Later on, Annie and Richard - two people of who dislike each another - end up sharing their past birthday experiences. (more)

Guest stars: Matthew Perry as Chandler Bing, Jonathan Silverman as Jonathan Eliot, Constance Towers as Barbara, Lou Felder as Don,

Caroline and The Folks - Caroline in the City Season 1

Caroline and the ATM

When Caroline is unable to take cash out from her local ATM, she meets up with her bank personnel to retrieve the money. However, the surveillance camera has captured her in an awkward moment, thus Caroline is too embarrassed to let the manager view the tape of her transaction. Meanwhile, Richard finds it difficult to end a relationship with an unstable woman named Shelley. (more)

Guest stars: Lauren Graham as Shelley, Ileen Getz as Mrs. Banks,

Caroline and the ATM - Caroline in the City Season 1

Caroline and The Balloon

Caroline is thrilled when she gets to relive her childhood dream: as her comic strip is showcased as the newest balloon in a Thanksgiving Day parade but chaos ensues afterwards, when the balloon is set free and injures Wessonality Float hostess, Florence Henderson. Meanwhile, Richard's girlfriend, Shelley - an animal activist confronts a fur wearing member of the public, much to Richard's embarrassment. (more)

Guest stars: Lauren Graham as Shelley, Florence Henderson as herself,

Caroline and The Balloon - Caroline in the City Season 1

Caroline and The Opera

When Caroline's favourite, Aunt Mary pays a visit, she arranges for her niece to go out on a date with an old boyfriend, who is now a successful doctor. As a result, Del feels threatened and is therefore determined to show Caroline the level of his commitment. Meanwhile, Richard contemplates breaking up with Shelley, seeing as her new age philosophies are beginning to grate on his nerves. (more)

Guest stars: Jean Stapleton as Aunt Mary, Peter Krause as Peter Weimerling, Lauren Graham as Shelly,

Caroline and The Opera - Caroline in the City Season 1

Caroline and The Xmas Break

Caroline and Del plan a Xmas vacation in Paris, with the assistance of a world weary travel agent, (Lorna Luft, real life sister and singer to Liza Minnelli). But when they find that they'll have to reschedule the trip for April, Del gets a case of commitment phobia and the pair find themselves facing a final break-up. Richard meanwhile, in his continued efforts to split up with Shelley, enlists Charlie by getting him to ask her out on a date. (more)

Guest stars: Lorna Luft as travel agent, Lauren Graham as Shelly,

Caroline and The Xmas Break - Caroline in the City Season 1

Caroline and The Gift

When Caroline realises the xmas gift Del gave her might have been expensive, she ponders the message he may be trying to send her in regards to their relationship. Richard is excited when he gets his first client - a woman who wants him to paint her in the nude as a surprise birthday gift for her boyfriend. (more)

Guest stars: Fabiana Udenio as Donna, Robert Miano as Pauly Brown, Keene Curtis as Mr. Davies,

Caroline and The Gift - Caroline in the City Season 1

Caroline and The Watch

When Caroline and Richard bicker over their shared workspace, Caroline finds the perfect solution when she purchases an antique partner's desk from the desks' original owners, writing and life partners, Vick Stansky and Stella Dawson. A guilt-ridden Del attends the funeral of a long-term employee to whom he never gave a raise when he was alive. (more)

Guest stars: Morey Amsterdam as Vick Stansky, Rose-Marie as Stella Dawson,

Caroline and The Watch - Caroline in the City Season 1

Caroline and The Married Man

Richard sets Caroline up on a date with Tom, an arts council member, who happens to hold the key to Richard's future as a successful artist. But when he finds out that he is married, Richard is split between protecting a friend and furthering his career. Meanwhile, Del finds out that Caroline is dating again and sees Annie for advice on how to deal with the situation. (more)

Caroline and The Married Man - Caroline in the City Season 1

Caroline and the 28 Pound Walleye

When Caroline's hometown of Pesthigo honours her by dedicating a park in her name, she returns to Wisconsin to visit her parents, Margaret and Ted, as well as to contend with her younger Brother, Chris who always manages to upstage her success. Elsewhere, Annie performs a good deed by allowing her Cats understudy a chance to perform in the musical but later finds that there may be a motive behind her collegues's actions. (more)

Guest stars: Paul Castree as Chris, Mariette Hartley as Margaret Duffy, Earl Holliman as Fred Duffy,

Caroline and the 28 Pound Walleye - Caroline in the City Season 1

Caroline and the Bad Date

Annie re-introduces Caroline to the wonderful world of dating by taking her out on a manhunt. But when Caroline thinks she has met the perfect man she later finds that he is not all that he seems to be. Del convinces Richard to go out on a double date but their friendship is put to the test when they run into one of Del's old flames, of whom has a thing for Richard. (more)

Guest stars: Dan Cortese as Scott,

Caroline and the Bad Date - Caroline in the City Season 1

Caroline and The Proposal

Sharon Lawrence guest stars. When Del surprises Caroline with a marriage proposal, Richard feels that he is no longer wanted and decides its time to look for another job. However, when he walks into a job agency's office, he becomes embroiled in a plan that evidently spins out of control. Annie convinces a confused Caroline that Richard has feelings for her and Caroline confronts Richard head on about his hidden feelings before giving Del an answer to his proposal. (more)

Guest stars: Sharon Lawrence as Maddie, Cathy Ladman as elevator lady,

Caroline and The Proposal - Caroline in the City Season 1

Caroline and The Kid

Caroline and Richard are hired by a wealthy man to paint a mural for his son, Martin. But by the time they arrive at the house, the pair are faced with a spoiled brat who tries to test their patience. Meanwhile, Del's competitive nature surfaces when Caroline's ex-boyfriend, Marco visits. (more)

Guest stars: Sam Gifaldi as Martin, Gregory Itzin as Mr. Lepner, Lupe Ontiveros as Rosa,

Caroline and The Kid - Caroline in the City Season 1

Caroline and The Ex-Wife

When Del takes Caroline on a weekend trip, they unexpectedly run into Del's bitter ex-wife, Jill and her boyfriend, Blair. Later, he is thrilled for his ex when Del learns that the pair are engaged with one less alimony payment to contend with. Yet when Blair secretly flirts with Caroline, she and Del contemplate whether to protect Jill or their future joint bank account. Meanwhile, Richard has to contend with Annie's argumentative family, made up of her parents, her brother and grandfather. (more)

Guest stars: Joely Fisher as Jill, Henry Johnson as Blair, Adam Ferrara as Pete Spadaro, Joseph Bologna as Lou Spadaro, Candice Azzara as Angie Spadaro, Kenny Johnson as Blair,

Caroline and The Ex-Wife - Caroline in the City Season 1

Caroline and The Bridesmaids

When Caroline entrusts Annie with various maid-of-honour duties, she learns that Annie's strong traits aren't dependability and punctuality. As a result, their preparation for the wedding evidently puts a lot of strain on their friendship. Also Del discovers his friends are unreliable and so he turns to Richard as a last resort. Christine Romeo (Eric Lutes's real-life wife) and Kenny Williams (Amy Pietz's real-life husband) appear as bridesmaid and usher respectively. (more)

Guest stars: Melora Hardin as Beth, Tia Riebling as Vicki, Christine Romeo as Linda, Tony Carlin as Greg, Pat Finn as Steve,

Caroline and The Bridesmaids - Caroline in the City Season 1

Caroline and Richard's Mom

Caroline helps Richard confront unresolved issues with his estranged mother, when she makes a surprising visit to New York. Later Natalie tries to impress Caroline with her business connections by introducing her to NBC president, but this in turn causes problems for both Caroline and Natalie. (more)

Guest stars: Warren Littlefield as himself, Elizabeth Ashley as Natalie Karinsky, John Ratzenberger as Mr. Berman, Matt Battaglia as Joseph,

Caroline and Richard

Caroline and The Cereal

When Caroline's agent James lands a promotional cereal deal for Caroline In The City, Caroline's initial delight and optimism turns sour when she discovers that a pushy corporate executive may tarnish her reputation with a sleazy new cereal design, after Richard discovers something wrong with it. Meanwhile a jittery Del, panics as his wedding day arrives - and yet he doesn't know how to dance. Hence, Annie and Charlie both step in to help him over this difficulty. (more)

Guest stars: Meshach Taylor as James, Vicki Lewis as Merle,

Caroline and The Cereal - Caroline in the City Season 1

Caroline and The Movie

When Caroline and Annie discover that John Landis is in town to shoot a new movie, they both jump at the chance to become extras. Annie's excitement turns to sheer bliss when she learns that her crush, is starring in the project. Meanwhile, Del and Charlie discover that Del's Porsche has been involved in a case of mistaken car identity, which leads them on an adventure on the streets of New York and sparks fly between Caroline and Richard on the set of the John Landis film when they are being cast opposite each other and are instructed to kiss. (more)

Guest stars: Robby Benson as himself, John Landis as himself, Kathy Griffin as DMV Clerk,

Caroline and The Movie - Caroline in the City Season 1

Caroline and The Wedding

Caroline and Del's wedding day nears and Caroline is confused by a state of anxiety and stress, whilst Del experiences panic attacks. Their priest is called out of town and a new priest, going by the name of takes over. Richard decides to come clean about his feelings and confess his love for Caroline by writing a love letter which he leaves on her table, in a last-ditch effort to stop her from marrying Del. But just when he thinks that her fate is already sealed, he makes some hasty decisions. (more)

Guest stars: Michael McKean as Father Damian, Candice Azzara as Angie Spadaro,

Caroline and The Wedding - Caroline in the City Season 1

watch caroline in the city season 1

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