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Season 1 Season 2 Season 3 Season 4
At the end of second season Julia, Richard's "sincere amore" showed up and when Caroline realized that she loves Richard he was already married to Julia. The pressure between them was rising even despite that Caroline met Trevor.
A remorseful Caroline panics when she realizes that several hours have passed since she poured her heart out to Richard on his answering machine - and she hasn't heard a response from him. Meanwhile, Annie, heartbroken over her stalled television acting career, returns from Los Angeles just in time to help untangle Caroline's love life. Elsewhere, Del is shocked to learn that his current girlfriend, may not be all she appears to be, and Richard's love Julia arrives with some surprising news for Caroline.
Guest stars: Cindy Ambuehl as Kristin,
Caroline realizes that the constant aching in her neck could be related to the stress she feels over her unresolved feelings toward Richard, but she doesn't let it get in the way of helping Richard navigate through troubled waters with Julia. Meanwhile, Annie must sort through her own anger when she is denied her old job with "Cats." Del neglects his business partnership with Charlie while trying to land an important account, but in the end realizes that Charlie has a better head for business than he ever gave him credit for.
Guest stars: Michael Ensign as Mr. Fogel, Barry Thompson as concierge,
When Caroline discovers that she's been receiving free cable, her honesty with the cable company gets her into deep trouble with her not-so-truthful neighbors. Meanwhile, Julia throws Richard a surprise birthday party, but Richard is not in the mood to celebrate when he discovers that his ex-therapist wants to date Annie.
Guest stars: Rex Smith as therapist, Peter Siragusa as Victor,
Caroline feigns having read a writer's (guest-star Tony Carreiro) novel to impress him, but their first date is a disaster as Caroline's charade quickly crumbles. Meanwhile, Richard jumps to Julia's rescue when her waitress job at Remo's leaves her customers hungry for attention. Also, inspired by the wisdom of a fortune cookie, Charlie believes that he and Annie are meant to be together. Del meets a woman (guest star Christine-Romeo, Lute's real-life wife) on her honeymoon who has passion to spare.
Guest stars: Tony Carreiro as James Clark,
It's a game of messy politics when Caroline will not endorse a local councilman, who is inspired by her comic strip, while Del conjures up a promotional campaign. Meanwhile, the politician shows an interest in Richard's art, pitting Richard against his personal ethics and his dwindling bank account. Elsewhere, Annie tries to convince her visiting young cousin Jennifer (guest-star Haylie Johnson) that the inhabitants of the big city are untrustworthy, but Jennifer's innocent nature may end up being a lesson for Annie.
Guest stars: Jim Abele as Councilman Robert Lake, Haylie Johnson as Jennifer,
Caroline goes out of her way to help Richard find a misplaced and beautiful, albeit cursed, family wedding ring for Julia. Also, Del and Charlie come up with a creative plan to make "Caroline in the City" the star attraction on the Christmas tree at Rockefeller Center. Meanwhile, a delighted Annie makes her cabaret singing debut, but the stars in her eyes keep her blind to the real thing - a band member, Seth, who only has eyes for Annie.
Guest stars: Dan Futterman as Seth, Keone Young as Fong, Parry Shen as Tim, Hamilton Von Watts as Paul, Rita McKenzie as Rita,
Caroline is excited to go on a blind date that Julia has set for her and handsome Trevor, while Richard becomes an obstacle to the evening's possibilities. Elsewhere, Annie enlists Del to help her seek revenge on her former classmates at her high school reunion, but she finds that most of her plans don't make the grade. Also, Charlie's new water-heavy diet finds him swimming in trouble when he accidentally attends a stranger's funeral.
Guest stars: Keone Young as Fong, Jeff Blumen Krantz as Phil, Bonnie Hillman as coach Reynolds, Lynne Marie Stewart as Aunt Pat,
When Annie is visited by her old singing teacher, Caroline helps Annie pretend to still have her "Cats" role, an act that may have a surprise ending. Meanwhile, a desperately broke Richard joins Charlie in a quick money-making scheme, but soon finds that there is a high price to pay. Also, Del discovers something new about himself - he loves the theater.
Guest stars: Harriet Samson Harris as Miss McGowan, Edward Hibbert as Mr. Randolph, Pat Crawford Brown as Sadie,
Caroline ponders motherhood when her friend and former assistant, Jeannie, asks Caroline for a maternal donation. Meanwhile, Richard struggles to live up to Jeannie's legacy as Caroline's most dedicated and fun-filled assistant. Charlie stalls out trying to help Del get his beloved Porsche back.
Guest stars: Anita Barone as Jeannie, Susan Krebs as Doria, Edith Fields as Nina, Marsha Clark as receptionist, Rick Gianasi as Roberto,
Caroline tries to convince an insecure Del that he has the potential to be a great parent after Del is shocked to discover that he is the father of a 10-year-old girl. Meanwhile, Annie convinces a reluctant Richard to encourage her budding artist brother, Pete, but Richard exacts a price from Annie for his services. Also, Charlie feels threatened by Del's new focus.
Guest stars: Susan Walters as Laura, Kelsey Mulrooney as Becky Stevens, Adam Ferrara as Pete Spadaro,
Richard relives his tortured youth when he confronts his former piano teacher, Marvin Hamlisch, and accuses the Grammy Award-winning composer of plagiarism. Meanwhile, Caroline starts dating a former blind date, Trevor, but Trevor's possessive dog trains Caroline to stay on a long leash. Later, using all of her acting skills, Annie comes to Richard's rescue.
Guest stars: Marvin Hamlisch as himself, Mary Lou Rosato as Olga,
Discreetly planning to ease Caroline's homesick holiday blues, Richard goes to great lengths to get a gift for Caroline that inspires suspicion in Julia and sleuthing from Caroline and Annie. Meanwhile, a local car dealer, Crazy Fred, helps Richard make some extra Christmas money. Also, Del plans to buy a used Porsche so that he and Charlie can keep up a cool appearance.
Guest stars: David Leisure as Crazy Fred, Jennifer Crystal as Kathy, Donald Berman as Crazy Eugene,
Caroline winds up spending Christmas with Del's family when a snowstorm grounds her parents in Wisconsin. Frantic to find a last-minute gift for Del's mother, Eleanor (guest-star Debra Mooney, Meego), Caroline grabs a decanter out of the closet, only to find it was one that Del's mother had given her. Meanwhile, Annie and Richard bond when they are snowed in together at the airport with Julia. Also, Charlie and his father, Doc, share their first Christmas together.
Guest stars: Deborah Mooney as Eleanor Cassidy, John Reilly as King Cassidy, Megan Mullally as Vanessa, Bill Daily as Doc, Christopher Carroll as Good Samaritan,
When Caroline is tapped as a celebrity guest star for a quiz show, her jitters prompt Richard to help her study, much to Julia's chagrin. Meanwhile, Annie's new boyfriend, Seth, and his family are a little too close for comfort.
Guest stars: David Kriegal as Seth, Victor Raider-Wexler as Marv, June Gable as Naomi, Jenica Bergere as Kristin, Lyndsey Fields as Ms. Stratton, Eric Whitmore as Dr. McMurty, Alexis Kleyla as young Caroline, Max Freedman as Whiz Kid,
Informed by Annie of Caroline's unspoken love for him, Richard confronts Caroline, who tells him that it's a thing of the past. To prove she's over him, Caroline throws a lavish party for Richard, Julia and Trevor. Later, when all four party members end up in the hospital with food poisoning, Caroline and Richard's unresolved tensions heat up the emergency room. Meanwhile, Annie helps Del beat his competitive brother, Garner, at his own game.
Guest stars: Andrew Heckler as Garner Cassidy, Marianne Muellerleile as Marva, Fred Sanders as Joe, Bob Glouberman as Dr. Dorfman,
When Julia tells Caroline that it's not easy being on the outside of her close working relationship with Richard, Caroline quickly, and mysteriously, learns what it's like to walk a mile in Julia's shoes. Simultaneously, Julia also experiences what it's like to be Caroline for a day. As part of her unusual experience, Caroline faces a romantic evening with Richard that could bring her dreams to reality.
As Caroline struggles with commitment issues over Trevor, Richard inadvertently causes a rift between Caroline and her new beau. Meanwhile, Annie is delighted to learn that her mother, Angie is finally going to move out of Annie's apartment. Del and Charlie plot a "Groundhog Day" publicity stunt for Caroline's card line, but a missing groundhog shadows their enthusiasm for the project.
Guest stars: Maria Canals as Maria, Mik Scriba as Sal, Peter Van Norden as Lou,
When Caroline is insulted by a local cabbie, Adamo, she takes her case to higher powers at the travel commission. Meanwhile, Richard frustrated by a "painter's block," becomes obsessed with computers when he joins a cybercafe. Also, Annie finally lands an appointment with hairstylist guru Olaf, but her ambitions are cut short by another one of Del and Charlie's business schemes.
Guest stars: Saverio Guerra as Adamo, Eric Allan Kramer as Olaf, Alaina Reed Hall as Stanchfield, Chris Parnell as Gene, Robert Louis Kempf as Kenny, Nicole Bilderback as Assistant, Stacey Silverman as Suzanne,
Richard is nervous when Julia's father, Carlo Mazzone, takes him on a bonding trip in a small plane, but Caroline helps him through the rough moments. Later, Caroline realizes that Richard's life may be in danger, due to Carlo's track record with many men in Julia's past. Meanwhile, Annie is pleasantly surprised when she goes on a date arranged by her mother, but the relationship takes a turn when her new beau realizes he must answer to a higher power. Also, Del is convinced that he can write a funnier comic strip than Caroline.
Guest stars: Charles Cioffi as Mr. Mazzone,
Caroline must hire a new cartoon colorist when Richard finally quits after he and Julia move into their glamorous new home, courtesy of Julia's recent inheritance; however, both Caroline and Richard have trouble saying goodbye. Meanwhile, when Julia convinces Richard that they should solve their marital woes by seeing a counselor, Dr. Leslie, they end up losing their therapist to Caroline, when Dr. Leslie applies for Richard's old job.
Guest stars: Leslie Jordan as Dr. Leslie, Garry Shandling as patient,
In the second half of this one-hour episode, a troubled former patient tracks down Dr. Leslie at Caroline's apartment. Also, Caroline and Trevor try to come to terms over their own troubled relationship, while Del and Charlie have their own unresolved issues.
Guest stars: Leslie Jordan as Dr. Leslie,
Caroline is reluctantly pulled into the national spotlight with Jo Anne Worley when Del and Charlie get a deli owner to re-name a Worley sandwich after "Caroline in the City." Later, Caroline is booked on Live! With Regis & Kathie Lee where she must confront audience favorite Worley about their celebrity battle for menu space. Elsewhere, Annie helps a frustrated Richard face life with a large bank account for the first time in his life. Television anchors Maureen O'Boyle and Jerry Penacoli and Len Lesser (Uncle Leo on Seinfeld) also guest-star.
Guest stars: Jo Anne Worley as herself, Regis Philbin as himself, Kathie Lee Gifford as herself, Stephanie Faracy as Faye, Len Lesser as waiter, Maureen O'Boyle as herself, Jerry Penacoli as himself, Amy Tolsky as producer, Cynthia Frost as customer,
When Caroline's mother, Margaret Duffy, visits Caroline for a mother-daughter People magazine shoot, tensions rise over unexpressed feelings. Meanwhile, Annie tries to convince Caroline that the only way to grow closer to her mother is to be honest. Elsewhere, Del and Charlie visit Atlantic City with a prospective investor in Cassidy Greeting Cards, but with Richard as their road trip companion, their future turns into a house of cards. Candice Azzara also guest-stars as Angie Spadaro.
Guest stars: Edie McClurg as Margaret Duffy, Michael Kagan as pit boss, David Graf as Mr. Wolfe, Aaron Lustig as photographer, David Bickford as Bandoo the Magnificent, Patience Cleveland as Lil,
Caroline is drawn into Angie Spadaro's New Jersey-based world when she tries to help Angie deal with the pending nuptials of her ex-husband, but Angie's daughter, Annie, doesn't help matters when she keeps a secret from her mother: she actually likes her new stepmother-to-be. Meanwhile, a reluctant Richard is called to jury duty and must go through trial and error selection for a specific case with the help of a fellow jury expert (Zelda Rubenstein, Poltergeist). Also, Del and Charlie feign a gay relationship with each other in order to receive better insurance benefits, but their plan presents a challenge for Del when he becomes attracted to Susan (guest-star and supermodel Angie Everhart), the sexy roommate of their gay insurance agent. Mitzi McCall (Alright, Already) also guest-stars.
Guest stars: Candice Azzara as Angie, Zelda Rubinstein as Phyllis, Angie Everhart as Susan, Sean Masterson as Todd, Rhoda Gimignani as Gail, Kathryn Kates as Ginny, Mitzi McCall as Lois, David Courier as Lester, Allen Gilmore as Phil,
The third season finale finds Richard and Julia agreeing that she'll go to Spain to party with her friends in the summer, while Richard stays in New York to begin painting again. But when Caroline inadvertently tells Richard that she thinks Julia is having an affair with a Spanish bullfighter, Jose (guest-star Jose Solano, Baywatch), Richard takes off for Spain to confront Julia.
Guest stars: Samantha Smith as Monica, Jose Solano as Jose, Peter Mackenzie as Lionel, Jackie Debatin as Simone, Philippe Bergeron as Andre, Magda Harout as Contessa,
IN PART 2, realizing that Julia did not sleep with the bullfighter, Caroline and Annie fly to Spain to right their wrong, and they run into Richard during the running of the bulls (with an appearance by 12 live bulls). Meanwhile, a bitter hotel maid tries to cope with Julia's messy suite. Del coaches a young Little League player in hopes of impressing his mother, but Charlie calls a timeout on Del's efforts. Also, upon Caroline's return home, she finds that her boyfriend, Trevor has left her and moved out; but her spirits are lifted when Richard shows up at her doorstep.
Guest stars: Liz Torres as Elizabeth, Samantha Smith as Monica, Jackie Debatin as Simone, Ana Gabriel as nurse, Rene Moreno as bullfighter,
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