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The Best Episodes of Caroline in the City Season 1

Every episode of Caroline in the City Season 1 ranked from best to worst. Discover the Best Episodes of Caroline in the City Season 1!

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Episode Rankings

  1. #1 Fan Favorite
    Caroline in the City Season 1 Episode 18 - Caroline and the Ex-Wife
    8.0/10(83 votes)

    S1:E18

    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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  2. Caroline in the City Season 1 Episode 1 - Caroline in the City
    7.7/10(101 votes)

    S1:E1

    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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  3. Caroline in the City Season 1 Episode 11 - Caroline and the Gift
    7.5/10(58 votes)

    S1:E11

    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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  4. Caroline in the City Season 1 Episode 14 - Caroline and the Watch
    7.5/10(62 votes)

    S1:E14

    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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  5. Caroline in the City Season 1 Episode 16 - Caroline and the Proposal
    7.5/10(59 votes)

    S1:E16

    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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  6. Caroline in the City Season 1 Episode 23 - Caroline and the Wedding
    7.5/10(57 votes)

    S1:E23

    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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  7. Caroline in the City Season 1 Episode 3 - Caroline and the Gay Art Show
    7.3/10(67 votes)

    S1:E3

    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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  8. Caroline in the City Season 1 Episode 10 - Caroline and the Christmas Break
    7.3/10(68 votes)

    S1:E10

    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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  9. Caroline in the City Season 1 Episode 6 - Caroline and the Folks
    7.2/10(77 votes)

    S1:E6

    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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  10. Caroline in the City Season 1 Episode 17 - Caroline and the Kid
    7.2/10(51 votes)

    S1:E17

    Ultra-competitive Del has feelings of inadequacy after meeting Caroline's debonair ex-boyfriend Marco, especially when the towels come off at the gym; Caroline and Richard are hired to paint a mural for the bedroom of Martin Lapper, a demonic spoiled rich kid.

    Director:Tom Cherones
    Writers:Bill Masters, Wil Calhoun

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  11. Caroline in the City Season 1 Episode 19 - Caroline and the Movie
    7.2/10(65 votes)

    S1:E19

    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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  12. Caroline in the City Season 1 Episode 2 - Caroline and the Mugger
    7.1/10(73 votes)

    S1:E2

    Richard is mugged and robbed of his wallet and portfolio - containing Caroline' s drawings.

    Director:James Burrows
    Writer:Unknown

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  13. Caroline in the City Season 1 Episode 5 - Caroline and the ATM
    7.1/10(67 votes)

    S1:E5

    Being too picky could cost Caroline the chance to reclaim money she lost at a malfunctioning ATM, since she doesn't really want to bank staff to see her picking her nose on the videotape record of the transaction. Meanwhile, Richard may end up in the doghouse after he attempts to dump the clinging Shelly on the pretext that he is allergic to her beloved dog.

    Director:Rod Daniel
    Writer:Mark Wilding

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  14. Caroline in the City Season 1 Episode 7 - Caroline and the Opera
    7.1/10(62 votes)

    S1:E7

    Caroline is annoyed that Del refuses to accompany her to the opera; then her interfering Aunt Mary arranges a blind date with an old high school classmate of Caroline's, who turns out to be handsome, successful and rich.

    Director:Tom Cherones
    Writers:Marco Pennette, Fred Barron

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  15. Caroline in the City Season 1 Episode 8 - Caroline and the Balloon
    7.1/10(60 votes)

    S1:E8

    Caroline is blown away by an opportunity to march in the Thanksgiving Day Parade - something she had dreamed of since high school mononucleosis kept her out of her marching band - when the giant balloon of her character Caroline escapes, injures parade marshal Florence Henderson, and threatens Staten Island.

    Director:Tom Cherones
    Writer:Bill Prady

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  16. Caroline in the City Season 1 Episode 12 - Caroline and the Married Man
    7.1/10(55 votes)

    S1:E12

    Richard sets Caroline up on a date with a man (Gravitte) who can get him a civic commission for an important mural, and they hit it off; then Richard discovers the guy is married.

    Director:Tom Cherones
    Writer:Wil Calhoun

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  17. Caroline in the City Season 1 Episode 9 - Caroline and the Convict
    7.0/10(58 votes)

    S1:E9

    Annie is really in love with her new boyfriend, a recent ex-con who did time for breaking and entering - and who is the obvious suspect when Caroline's apartment is burgled. Richard is upset because one of the stolen items was his painting of his mother's womb.

    Director:Rod Daniel
    Writer:Rob Lotterstein

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  18. Caroline in the City Season 1 Episode 15 - Caroline and the Bad Date
    7.0/10(56 votes)

    S1:E15

    Del asks Richard to join him on a double date with two gorgeous models; Caroline meets a man buying a sweater, but he turns out to be a paranoid bore.

    Director:Tom Cherones
    Writer:Bill Prady

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  19. Caroline in the City Season 1 Episode 20 - Caroline and the Cereal
    7.0/10(57 votes)

    S1:E20

    Caroline's agent (Taylor) likes the idea of featuring her comic-strip character on a cereal box, but the artist flakes out after a closer look at the product, which she feels has an unfortunate resemblance to a certain part of the female anatomy. A chaotic focus group sessions does little to allay her misgivings.

    Director:Pamela Fryman
    Writer:Unknown

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  20. Caroline in the City Season 1 Episode 4 - Caroline and the Bad Back
    6.9/10(67 votes)

    S1:E4

    Richard and Del bend over backwards to help an injured Caroline complete her work in time for a deadline, but things go from bad back to worse when medication dulls her pain - and her mind - so Richard and Del have to finish the strip for her.

    Director:James Burrows
    Writer:Bill Prady

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  21. Caroline in the City Season 1 Episode 21 - Caroline and Richard's Mom
    6.9/10(54 votes)

    S1:E21

    Richard faces some childhood traumas when his mother (Ashley) makes a surprise visit: it seems she is given to claiming to know celebrities personally, and Richard has never quite gotten over her promise to have Salvador Dali look at his paintings. But Caroline doesn't know this when Natalie promises to get her own NBC Saturday morning cartoon show.

    Director:James Burrows
    Writers:Dottie Dartland Zicklin, Charles Harper Yates

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  22. Caroline in the City Season 1 Episode 22 - Caroline and the Bridesmaids
    6.9/10(52 votes)

    S1:E22

    Preparations for the wedding cause friction between Caroline and Annie, who can't seem to take her responsibilities as maid of honor seriously.

    Director:Tom Cherones
    Writers:Bill Masters, Wil Calhoun

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  23. Caroline in the City Season 1 Episode 13 - Caroline and the Twenty-Eight-Pound Walleye
    6.8/10(55 votes)

    S1:E13

    Caroline's parents (Holliman & Hartley) roll out the red carpet when she visits her home town for a ceremony in her honor, but something smells fishy when her brother (who has upstaged her all their lives) arrives with big news of his own.

    Director:Tom Cherones
    Writer:Unknown

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  24. Caroline in the City Season 1 Episode 24 - Caroline and the Condom
    6.7/10(50 votes)

    S1:E24

    Caroline's writers' block sends her down memory lane to Richard's first day on the job---a day with trouble in store for Caroline because she and Del had just rekindled their romance.

    Director:James Burrows
    Writers:Marco Pennette, Fred Barron

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Season 1 Ratings Summary

"Caroline and the Ex-Wife" is the best rated episode of Caroline in the City season 1. It scored 8.0/10 from 83 votes. Directed by Tom Cherones and written by Unknown, it aired on March 28, 1996. This episode is rated 0.3 points higher than the second-best, "Caroline in the City".