The Best Episodes of Caroline in the City

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8.0/10(83 votes)
#1 - Caroline and the Ex-Wife
S1:E183/28/1996
Del and Caroline's vacation takes an unexpected turn when they run into Del's bitter ex-wife Jill at his cabin. Meanwhile, Annie's brother Pete decides to quit the family business, which doesn't sit well with his parents.
Director:Tom Cherones
Writer:Unknown
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Director:Tom Cherones
Writer:Unknown
7.7/10(101 votes)
#2 - Caroline in the City
S1:E19/21/1995
Caroline hires Richard as her new colorist, and takes Annie's advice to try getting a date by throwing fruit out her window.
Director:James Burrows
Writers:Marco Pennette, Fred Barron, Dottie Dartland Zicklin
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Director:James Burrows
Writers:Marco Pennette, Fred Barron, Dottie Dartland Zicklin
7.8/10(47 votes)
#3 - Caroline and the Wayward Husband
S2:E255/13/1997
Richard prepares to run off with another just as Caroline is about to tell him how she feels.
Director:Will Mackenzie
Writer:Kim Friese
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Director:Will Mackenzie
Writer:Kim Friese
7.6/10(49 votes)
#4 - Caroline and Richard & Julia
S2:E245/13/1997
Richard's long-lost love arrives with bad news: she's getting married in two days, to arrogant and insanely jealous fashion designer Marcello. Not to be outdone, Richard concocts a coupling of his own - to Caroline, much to her astonishment. Meanwhile, Del's business is going bankrupt, so he reluctantly arranges a midnight meeting at Remo's with his arrogant father, who refuses to help him but does buy Del's Porsche at an instant profit to teach him a lesson. Annie is offered a part in a pilot for a new series starring Shadoe Stevens, and instantly calls New York to resign from Cats.
Director:Will Mackenzie
Writer:Bill Masters
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Director:Will Mackenzie
Writer:Bill Masters
7.5/10(62 votes)
#5 - Caroline and the Watch
S1:E142/1/1996
Caroline finds a watch in her new antique desk and tries to find its previous owners; meanwhile, Del learns that a deceased employee was an embezzler.
Director:James Burrows
Writer:Mark Wilding
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Director:James Burrows
Writer:Mark Wilding
7.5/10(59 votes)
#6 - Caroline and the Proposal
S1:E162/22/1996
When Richard learns of Del's proposing to Caroline, he goes searching for another job, and is seduced by his just-divorced employment counselor; Remo and Annie try to convince a skeptical Caroline that she's oblivious to Richard's feelings for her - and hers for him.
Director:James Burrows
Writers:Marco Pennette, Fred Barron
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Director:James Burrows
Writers:Marco Pennette, Fred Barron

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7.5/10(58 votes)
#7 - Caroline and the Gift
S1:E111/4/1996
Del's unexpectedly generous Christmas gift - a pair of ugly but valuable earrings - makes Caroline question his intentions. Richard paints a commissioned nude portrait of a beautiful woman (Udenio) who has a well-connected husband - well -connected in ""the Family,"" according to a frightened Remo. And Annie can't remember her New Year's Eve party at which she met a man who has since telephoned her to confirm their date.
Director:James Burrows
Writer:Bill Prady
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Director:James Burrows
Writer:Bill Prady
7.5/10(57 votes)
#8 - Caroline and the Wedding
S1:E235/16/1996
An ominous dream, an inexperienced priest and a surprising love letter threaten Caroline's wedding.
Director:James Burrows
Writer:Bill Masters
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Director:James Burrows
Writer:Bill Masters
7.5/10(51 votes)
#9 - Caroline and the Comic
S2:E811/26/1996
Richard's father asks for his son's help in reviving an old comedy routine.
Director:Howard Deutch
Writers:Marco Pennette, Fred Barron
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Director:Howard Deutch
Writers:Marco Pennette, Fred Barron
7.4/10(59 votes)
#10 - Caroline and the Cat Dancer
S2:E310/15/1996
Richard tries to adjust to his new apartment, where he is plagued by noisily amorous neighbors; Joe tries to adjust to the fact that Caroline plans to remain friends with Del; and Annie frantically tries to adjust her financial records when she is notified that the IRS is auditing her for 1993, a year she barely remembers. Her bad-tempered auditor is under fire for being too lenient with his clients, but when he learns she is a dancer in Cats, he strikes a deal: she'll ""never have to pay taxes again"" if she can get him an audition for the show. Enter 'producer' Del and 'director' Charlie. Meanwhile, disturbed by Joe's jealousy, Caroline makes up her mind to break a date with Del by telling him she's been called out of town.
Director:Michael Lembeck
Writers:Brian Hargrove, Jack Kenny
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Director:Michael Lembeck
Writers:Brian Hargrove, Jack Kenny
7.4/10(53 votes)
#11 - Caroline and the Singer
S2:E131/14/1997
Annie's sister Donna, who has come to town in hopes of reviving her singing career, discovers Richard's secret love letter to Caroline (inside Annie's diary) and uses it as inspiration for a new song, to Richard's horror and Annie's fury, since she has been using the letter to blackmail Richard into taking her mother to electrolysis appointments. Caroline is preoccupied with her perfect plain black pumps, which she left in Joe's apartment; after a fruitless quest to replace them, she sneaks in to retrieve them, and is found by a repentant Joe. Meanwhile, Del and Charlie get snowed in - inside Del's Porsche, with the keys and his cell phone locked in the trunk by Charlie.
Director:Will Mackenzie
Writers:Brian Hargrove, Jack Kenny
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Director:Will Mackenzie
Writers:Brian Hargrove, Jack Kenny
7.4/10(52 votes)
#12 - Caroline and the Nice Jewish Boy
S2:E611/12/1996
Joe refuses to accompany Caroline to an award ceremony because one of the sponsors uses animal products; so she calls former date Willard, whom she dumped because he was fat and balding. After Charlie takes him to a Jewish singles event by mistake, Del lies about his background to date an attractive woman who parents will only allow her to date Jewish men. Willard shows up a reformed hunk who only came to tell Caroline to go to hell - ""And I'm rich, too!"" Aghast that Del plans to tell Risa the truth only after they spend a weekend together, Caroline points out delicately that if they sleep together Risa will know only, because Del is a ""turtleneck kind of guy."" So Del books himself into hospital, telling Risa he needs his ""tonsils"" removed; but she shows up to confess that she is eloping with her former boyfriend, who isn't Jewish either. A reluctant Richard escorts Caroline and even more reluctantly dances with her. Just as they seem about to have a tender moment, Joe appears, having
Director:Will Mackenzie
Writer:Tom Leopold
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Director:Will Mackenzie
Writer:Tom Leopold
7.4/10(44 votes)
#13 - Caroline and the Bitter Beast
S3:E911/24/1997
When Annie discovers an old musical notebook among the possessions Richard wants to store in Caroline's locker, teasing leads to genuine surprise when one of Richard's compositions turns out to be the tune to ""The Way We Were,"" which won a Grammy award for Richard's summer camp instructor, Marvin Hamlisch. With Annie pretending to be his legal counsel, Richard braves Hamlisch's ferociously protective housekeeper Olga and steals the trophy, then begins hostage negotiations. Meanwhile, Caroline encounters her former blind date Trevor and they resume a relationship, complicated by Trevor's German Shepherd who remains stubbornly loyal to Trevor's former girlfriend.
Director:Shelley Jensen
Writer:Oliver Goldstick
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Director:Shelley Jensen
Writer:Oliver Goldstick
7.4/10(44 votes)
#14 - Caroline and the Used Car Salesman
S3:E1112/8/1997
Caroline becomes convinced that Richard is having an affair - but he is really moonlighting as a used car salesman to earn extra Christmas cash. Enter Del and Charlie in search of a used Porsche.
Director:Unknown
Writer:Unknown
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Director:Unknown
Writer:Unknown
7.4/10(42 votes)
#15 - Caroline and the Ultimatum
S4:E204/5/1999
Caroline gives Richard a matrimonial ultimatum; but on his way to propose to her, he is taken hostage in a video store holdup. He decides that escape will prove his manhood and worthiness of Caroline -- and when he is wheeled in by paramedics, he does indeed propose.
Director:Marco Pennette
Writer:Oliver Goldstick
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Director:Marco Pennette
Writer:Oliver Goldstick
7.3/10(68 votes)
#16 - Caroline and the Christmas Break
S1:E1012/14/1995
Botched attempts to plan a holiday trip with Del lead Caroline to reconsider their relationship; Annie brews an elaborate scheme to help Richard break up with Shelly.
Director:James Burrows
Writer:Unknown
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Director:James Burrows
Writer:Unknown
7.3/10(67 votes)
#17 - Caroline and the Gay Art Show
S1:E310/5/1995
Richard takes his paintings out of the closet when Caroline and Annie convince a gallery owner to consider them for an exclusive show - which turns out to be for gay artists only; Annie becomes entangled in Caroline's search for a new hair dresser - and her old hairdresser (Lerner) spots her at the gallery opening party.
Director:James Burrows
Writer:Unknown
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Director:James Burrows
Writer:Unknown
7.3/10(52 votes)
#18 - Caroline and the Ombudsman
S2:E224/22/1997
Caroline's having a really bad hair week because her shower's been out of commission for several days and she can't get the super in her building to repair it. A deliveryman at Remo's suggests she hire his brother-in-law who specializes in persuasion; then an aghast Del and Richard explain to her that she has inadvertently hired a hit man. Trying to protect Mr. Tedescu, Caroline shadows him to head off the hit, which involves getting Richard glued to the pipes in the Elevator Lady's apartment. Meanwhile, Annie's agent wants to make her famous by publicizing her saving an audience member's life with CPR. The catch is that the man was with his mistress and doesn't want any publicity - especially when his wife assumes that Annie is the other woman.
Director:Will Mackenzie
Writer:Bill Prady
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Director:Will Mackenzie
Writer:Bill Prady
7.3/10(50 votes)
#19 - Caroline and Victor/Victoria
S2:E711/19/1996
Annie poses as a man to prepare for a ""Victor/Victoria"" audition.
Director:Howard Deutch
Writer:Bill Masters
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Director:Howard Deutch
Writer:Bill Masters
7.3/10(50 votes)
#20 - Caroline and the Love That Dares Not Speak its Name
S3:E131/5/1998
Caroline is aghast that Annie blabbed to Richard about her feelings for him, and tries to avoid his questions by inviting in a hyper-anxious knife salesman. When Richard discovers the truth about the answering machine message Caroline left for him (and which Julia erased), the two finally confess their mutual attraction, but quickly agree that they have both moved on. But a dinner double date at Caroline's turns into a competition for happiest couple between Caroline & Trevor and Richard & Julia - until they all wind up in an emergency ward with food poisoning from Caroline's fish chowder. Meanwhile, Annie tries a song and dance routine to help Del and Charlie defend their greeting card trade show turf against Del's evil brother Garner.
Director:James Burrows
Writers:Brian Hargrove, Jack Kenny
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Director:James Burrows
Writers:Brian Hargrove, Jack Kenny
7.3/10(48 votes)
#21 - Caroline and the Reception
S3:E19/22/1997
An anxious Caroline, not aware that Julia intercepted his message, waits for Richard's response but isn't prepared for his ""Oh, why is it so difficult to say three words - I got married!"" Devastated, Caroline calls Del in the middle of the night and he rushes over - still handcuffed to his date Kristin, and must be released by an amused Annie with one of her collection of keys. Caroline impulsively throws a reception to honor the happy couple, at which she gets drunk, but things turn serious when Julia's wealthy father's chauffeur arrives and summons her to talk - and for the first time in her life Julia turns down her father's money and announces she will stay married to the man she loves.
Director:James Burrows
Writer:Unknown
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Director:James Burrows
Writer:Unknown
7.3/10(45 votes)
#22 - Caroline and the Booby Trap
S4:E911/30/1998
After Annie is beaten out in an audition by an untalented but well endowed rival, she announces her intention to have breast augmentation surgery during a Thanksgiving dinner already complicated by Del's turning up with a frozen rather than pre-cooked turkey and the bizarre behavior of mailroom Dave. Unable to talk Annie out of it, Caroline then beats her to the doctor's office to consider treatment herself after Richard's ill-timed admission that he has fantasized about her with larger breasts. A fantasy sequence in which Caroline imagines special treatment aboard a plane convinces her to stay with what she's got. Meanwhile, Richard has taken Caroline's riposte (that she has imagined him with darker, sexier hair) to heart, but when Del's current girlfriend shows up to rescue him from the effects of an amateurish home dye job, she realizes Del stood her up for Thanksgiving and storms out, leaving Richard to deal with a bad case of chemically induced hair loss.
Director:Ted Wass
Writer:Unknown
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Director:Ted Wass
Writer:Unknown
7.3/10(44 votes)
#23 - Caroline and the Secret Bullfighter (2)
S3:E265/18/1998
Caroline tells Richard she thinks Julia is having an affair with a bullfighter during her Spanish holiday.
Director:Michael Zinberg
Writer:Unknown
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Director:Michael Zinberg
Writer:Unknown
7.2/10(77 votes)
#24 - Caroline and the Folks
S1:E611/2/1995
Caroline must face dinner at Remo's with Del's parents alone when Del doesn't show up; Del is trapped on a stalled subway with Charlie, who insists on sharing his ideas for greeting cards for pets; and Richard's non-plans for his 30th birthday change when Annie visits to exchange swapped video rentals.
Director:James Burrows
Writers:Marco Pennette, Fred Barron
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Director:James Burrows
Writers:Marco Pennette, Fred Barron
7.2/10(65 votes)
#25 - Caroline and the Movie
S1:E194/4/1996
Caroline, Richard and Annie are cast as extras in a film, leading to some surprising developments for its star (Benson) and director (Landis) when Annie turns out to be a Benson fanatic - and Richard becomes insanely jealous of the extra who is to kiss Caroline. Meanwhile, Del's Porsche is towed, and when he claims it from the DMV, he gets someone else's Gremlin instead. When he tracks down the Gremlin's owner, the poor man pleads for more time - he's got a hot date with a woman who was really only impressed by the Porsche.
Director:Tom Cherones
Writer:Bill Prady
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Director:Tom Cherones
Writer:Bill Prady