The BEST episodes of Caroline in the City

#1 - Caroline and the Decanter

Season 3 - Episode 12 - Aired 12/15/1997

When Caroline's parents are stranded in Wisconsin by a snowstorm, Caroline reluctantly accompanies Del to his dysfunctional family Christmas - especially after he tells her that his mother still resents her never having brought a hostess gift the first time they met - leaving Charlie to house-sit Salty and attempt to spend some quality holiday time with his father. Meanwhile, while Richard tries to be enthusiastic about a delayed honeymoon trip to Hawaii, Annie tries to help Julia overcome her fear of flying with some tranquilizers that work all too well - and while defending herself to a furious Richard, lets slip the little fact that Caroline is ""still"" in love with him....

#2 - Caroline and the Guys in the Bathroom

Season 4 - Episode 1 - Aired 9/21/1998

Acting as narrator, the Elevator Lady brings us up to speed on the events at last season's close culminating in Richard and Caroline's first kiss. Desperately aroused, Caroline and Richard pause only long enough for Caroline to run to the bathroom to brush her teeth; but once there she is confronted by a vision of four men: ex-boyfriend Trevor, the first man she ever slept with, the high school coach she had a crush on, and the first little boy she ever kissed. An angry dialogue ensues, and an inflamed Richard, overhearing, strips down - only to be walked in on by an angry Annie, who accuses him of exploiting Caroline's vulnerable state. Then Caroline emerges from the bathroom naked, only to be confronted by Annie and Charlie, the latter having arrived with an urgent message from Del: Eagel Greeting Cards is going out of business. A mortified Caroline dresses and rushes to comfort Del, only to discover that he is celebrating the sale of his company to a major conglomerate, and to be pr

#3 - Caroline and the Big Night

Season 4 - Episode 7 - Aired 11/9/1998

Caroline and Richard's big night finally arrives, in the form of a romantic weekend booked in the perfect room at the perfect country bed and breakfast. What's wrong with this picture? Naturally everything: Richard's choice of the perfect negligée for Caroline to wear gets switched for Del's brother's barbeque apron; their room is given away to another couple who have gotten married after not seeing each other for 30 years; and the bed and breakfast is run by a bitter, bickering pair of neurotics who ultimately throw Caroline and Richard out. But Richard saves the day by getting Annie and Del to turn Caroline's apartment into a romantic fantasyland - which, we learn in the coda, they enjoy for several consecutive days...

#4 - Caroline and the Paper Chase

Season 4 - Episode 6 - Aired 11/2/1998

Del has hired Caroline and Annie to provide the voices for his new promotional video, but when he comes to pick them up it turns out they have to perform it for the boss first as a puppet show - about menstruation. While Annie is in her office, Caroline searches in Richard's desk for a highlighter and finds his divorce papers, and Richard angrily denounces her invasion of his privacy. Of course Annie immediately lifts the papers, is forced to hide them from Richard, sees them dumped down the corporate mail chute, and has to enlist Caroline's help to wheedle them back from the bizarre and hostile mail room staff - leaving a reluctant Richard and a strangely eager Charlie to act out the puppet show for Mr. MacDermott, who reveals that he is only doing the animated cartoon as part of a community service sentence. Discovering that the divorce papers are two months old but that Richard has not yet signed them, and is therefore technically still married, Caroline confronts him - and he confe

#5 - Caroline and the Secret Bullfighter (2)

Season 3 - Episode 26 - Aired 5/18/1998

On the eve of their moving in together, Caroline leaves Trevor alone as she dashes off to Spain, with Annie in tow, in an attempt to repair the damage she has done to Richard and Julia's marriage. Lunching at Remo's, they have seen Remo's new waitress wearing a diamond bracelet and realized it was she making love to José during the party. Richard arrives in Spain and the hotel maid, who hates Julia, directs him to the ""matador bar"" on the corner; but when he demands to speak to a ""worthless matador named José,"" every man in the bar stands up. By the time Caroline and Annie arrive, Richard has traced Julia to Pamplona, where she has gone to see the running of the bulls; unaware of the event, and distracted by the arrival of Caroline, Richard flees for his life and is trampled by the bulls - only mildly, as we discover. Meanwhile, Del suffers through endless bad pitches thrown by Monica's son while Charlie explains why he won't let the hopeless kid into the game, and discovers an unexpec

#6 - Caroline and the New Neighbor

Season 2 - Episode 20 - Aired 4/8/1997

Things get a little stiff when an demanding elderly new neighbor, who is driving an initially sympathetic Caroline nuts, asks Caroline and Annie for a really big favor - to help out with the removal of her dead, naked husband. Meanwhile, Richard tries to sell his car, but the only bidder is Louis, a bizarre individual claiming to be a minister and promising eternal life in exchange for the vehicle. Charlie, smitten with Sophia, the beautiful new waitress at Remo's, offers Richard $500 (which he makes driving the car as a gypsy cab) so he can give the car to Sophia as a love token; but Richard decides to keep the car and drive it as a cab himself. Through all this, Del is obsessed with the idea that he is losing his hair and his looks.

#7 - Caroline and the Proposal

Season 1 - Episode 16 - Aired 2/22/1996

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.

#8 - Caroline and the Singer

Season 2 - Episode 13 - Aired 1/14/1997

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.

#9 - Caroline and the Love That Dares Not Speak its Name

Season 3 - Episode 13 - Aired 1/5/1998

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.

#10 - Caroline and the Buyer

Season 2 - Episode 19 - Aired 4/1/1997

Del asks Caroline to help him woo one of his father's biggest clients, a greeting-card store magnate who misunderstands what the cartoonist has to offer. Meanwhile, Annie resents Richard's relationship with her mother, and a friendly game of bocci turns ugly.

#11 - Caroline and the Booby Trap

Season 4 - Episode 9 - Aired 11/30/1998

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.

#12 - Caroline and the Big Move (2)

Season 4 - Episode 22 - Aired 4/26/1999

As Caroline and Richard prepare to leave for Italy to visit his newborn son, Richard makes a confession that gives Caroline second thoughts about their future together: he never wanted to have children. But when he arrives alone in Italy, Richard discovers that Julia has abandoned the baby, and slowly becomes a model father. Meanwhile, Annie and Del begin a clandestine relationship. Flashing forward six months later, the series finale finds Caroline headed to the altar with Randy, when an unexpected guest arrives during the wedding ceremony: Richard, holding his infant son...

#13 - Caroline and El Niño (1)

Season 4 - Episode 21 - Aired 4/26/1999

After deciding they can't wait to get married, Caroline and Richard plan their nuptials for the following week. But while Caroline and Annie search for the perfect wedding dress, Richard shows up at the bridal shop with a bombshell announcement regarding his ex-wife: Julia has given birth to their son. Caroline gets an unexpected visit from Randy; and Annie and Del flirt with the idea of having a no-strings-attached fling.

#14 - Caroline and the Rotten Plum

Season 4 - Episode 3 - Aired 10/5/1998

Caroline settles into her new workplace, where she inadvertently - and immediately - ticks off office manager Plum, who banishes Caroline and Richard to the basement. Meanwhile, Annie lusts after her yoga teacher Jonathan, but learns from Angie that he is a former porn performer.

#15 - Caroline and the Secret Bullfighter (1)

Season 3 - Episode 25 - Aired 5/18/1998

Now that they are planning to move in together, Caroline and Trevor hold a rummage sale on Caroline's doorstep, but she can't bear to part with her things and winds up buying them back at a loss. All she manages to sell is Del's softball glove, which he needs because he is helping Charlie coach a Little League team; this surprises everyone until they meet Monica, the attractive mother of one of the boys. Meanwhile, planning to spend the summer in Spain, Richard and Julia throw themselves a bon voyage party (described by Caroline as a ""Eurotrash compacter""). While Julia shops, a distracted Richard is indifferent to the cook's ""perfect Bernaise sauce,"" so the indignant chef quits (and Remo gets the job on two hours' notice, with the new waitress from his restaurant as staff). Julia has celebrated by buying herself a flashy new diamond bracelet; and during the party, when Caroline and Annie sneak into the en suite bathroom, they accidentally overhear a man with a distinctive laugh making

#16 - Caroline and the Marriage Counselor (2)

Season 3 - Episode 24 - Aired 5/4/1998

#17 - Caroline and the Free Cable

Season 3 - Episode 4 - Aired 10/13/1997

Julia throws a surprise birthday party for Richard by inviting everyone in his address book, under the impression that they are his friends, which results in a gathering chiefly of his ex-therapists - one of whom is interested in Annie, to Richard's horror. Meanwhile, the discovery that she has been getting illegal free cable for years puts Caroline in a moral spin, since the rest of the building is hooked into her outlet and anxious for her not to do the right thing.

#18 - Caroline and the 28 lb. Walleye

Season 1 - Episode 13 - Aired 1/25/1996

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.

#19 - Caroline and the Condom

Season 1 - Episode 24 - Aired 8/5/1996

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.

#20 - Caroline and the Married Man

Season 1 - Episode 12 - Aired 1/11/1996

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.

#21 - Caroline and the Getaway

Season 2 - Episode 17 - Aired 2/25/1997

When Caroline calls her out on always blowing her off for male dates, Annie makes a deal: they will go away together for a weekend skiing trip and ignore men. Naturally, both immediately spot exceptionally interesting men: an old school chum of Caroline's who confesses to having had a mutual crush, and for Annie a handsome tycoon. Meanwhile, Richard is hoping that his relationship with a fellow philosophy student won't remain Platonic, but the tryst he arranges in Caroline's apartment while she is away is invaded by Del and Charlie, who intend to make themselves at home to watch sports.

#22 - Caroline and the Bar Mitzvah

Season 4 - Episode 10 - Aired 12/14/1998

Richard's Aunt Frieda announces that before she moves to Florida and wants to see Richard go through with the bar mitzvah he abandoned, and is willing to pay him $5,000 for the privilege. While an embarrassed Richard returns to Hebrew school, Caroline and Annie prepare a mocking party in his honor -- until Richard confesses to Caroline that he is doing it for the money only because he is humiliated by her having to pick up the tab for everything they do together. Meanwhile, Del gets a great deal in expensively tailored Italian suits, but won't admit they are several sizes too small for him.

#23 - Caroline and the Firing Squad

Season 4 - Episode 14 - Aired 1/25/1999

Caroline is appalled to discover that Del (currently obsessed with buying a new Porsche) is paying his partner Charlie to stay at home so that his bizarre ideas won't compromise Del's career. When she persuades Del to let Charlie attend a planning meeting, the plan backfires big time: Charlie is fired. Charlie decides he wants to travel in Europe, and Del does the right thing and gives him the money for his Porsche as severance. Meanwhile, Richard gets Annie a job posing for a cartoonist who starts dating her, but the deal is fishy: it turns out he is only interested in her when she is dressed as the bizarre science fiction heroine of his strip.

#24 - Caroline and the Horny Kid

Season 4 - Episode 13 - Aired 1/18/1999

Del and Caroline participate in the company's mentoring program, but Caroline's adolescent charge Stan develops an embarrassing crush on her, while Del's turns into a teenage fixer who takes over Del's professional and personal lives with impressive competence. Meanwhile, Reg tries to convince Richard to sell his art, but the results are disastrous: a coffee house show is a fiasco, and when Richard desperately tries to emulate a subway hawker and sell his works to consumers, he is busted by an undercover cop who confiscates his art.

#25 - Caroline and the Big Bad Bed

Season 4 - Episode 12 - Aired 1/11/1999

Caroline becomes upset over what she sees as Richard's refusal to share his private life with her -- which comes to a head when Reg Preston's girlfriend kicks him out and he moves in temporarily with Richard. Meanwhile, Del and Annie forge a temporary truce and attempt to find dates for each other at the gym. Del strikes out, but Annie finds an obliging man mountain she'd ""like to hire a team of sherpas and climb.""