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Caroline and the Christmas Break
Caroline in the City - 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.
Caroline in the City: Season 1 - 24 Episode s
1x1 - Caroline in the City
September 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.
1x2 - Caroline and the Mugger
September 28, 1995
Richard is mugged and robbed of his wallet and portfolio - containing Caroline' s drawings.
1x3 - Caroline and the Gay Art Show
October 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.
1x4 - Caroline and the Bad Back
October 12, 1995
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.
1x5 - Caroline and the ATM
October 19, 1995
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.
1x6 - Caroline and the Folks
November 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.
1x7 - Caroline and the Opera
November 9, 1995
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.
1x8 - Caroline and the Balloon
November 16, 1995
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.
1x9 - Caroline and the Convict
December 7, 1995
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.
1x10 - Caroline and the Christmas Break
December 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.
1x11 - Caroline and the Gift
January 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.
1x12 - Caroline and the Married Man
January 11, 1996
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.
1x13 - Caroline and the Twenty-Eight-Pound Walleye
January 25, 1996
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.
1x14 - Caroline and the Watch
February 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.
1x15 - Caroline and the Bad Date
February 15, 1996
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.
1x16 - Caroline and the Proposal
February 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.
1x17 - Caroline and the Kid
March 14, 1996
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.
1x18 - Caroline and the Ex-Wife
March 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.
1x19 - Caroline and the Movie
April 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.
1x20 - Caroline and the Cereal
April 18, 1996
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.
1x21 - Caroline and Richard's Mom
April 25, 1996
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.
1x22 - Caroline and the Bridesmaids
May 9, 1996
Preparations for the wedding cause friction between Caroline and Annie, who can't seem to take her responsibilities as maid of honor seriously.
1x23 - Caroline and the Wedding
May 16, 1996
An ominous dream, an inexperienced priest and a surprising love letter threaten Caroline's wedding.
1x24 - Caroline and the Condom
August 5, 1996
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.