Caroline hires Richard as her new colorist, and takes Annie's advice to try getting a date by throwing fruit out her window.
Richard is mugged and robbed of his wallet and portfolio - containing Caroline' s drawings.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Preparations for the wedding cause friction between Caroline and Annie, who can't seem to take her responsibilities as maid of honor seriously.
An ominous dream, an inexperienced priest and a surprising love letter threaten Caroline's wedding.
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.
Three months have passed, and Caroline is thinking about advertising for a new assistant, so Charlie tries to demonstrate he would be perfect for the job and knocks Salty out the window. Sparks fly between Caroline and the vet who treats Salty, despite her fears that at 24 he is much too young for her. Meanwhile Richard, having failed as an artist in Paris (his only customer is knocked into the Seine just before buying some paintings), returns to New York and is forced to take a menial job in an ice cream parlor, where he just misses seeing Caroline on her first date with Joe, during which they helped raid an animal experimental laboratory and were arrested. (One of the participants is Shelly, still wistful about Richard, in her final appearance to date.) Caroline wakes up in bed with Joe and is unable to sneak out before he wakes and demands to see her again that evening, and on her way home she and Richard suddenly meet face to face.
Realizing Caroline never received his love letter, Richard labors to retrieve it from her friend's apartment.
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.
When Caroline's young, new boyfriend says 'I love you' far too soon, she decides they should see other people. Meanwhile, Annie agrees to teach Richard how to drive after he inherits his aunt's car.
Del starts his own greeting card company, Eagle Greeting Cards, and Caroline reluctantly joins. Meanwhile, Richard is chosen to paint a mural for the city, which turns out to be in a shady part of town.
Joe refuses to accompany Caroline to an award ceremony because one of the sponsors makes mink coats. Meanwhile, Del lies about his background to date an attractive woman whose parents will only allow her to date Jewish men.
Annie poses as a man to prepare for a ""Victor/Victoria"" audition.
Richard's father asks for his son's help in reviving an old comedy routine.
When Salty begins behaving oddly, Joe recommends that Caroline consult a cat therapist, who decides it's really Richard who needs help.
Annie's mother arrives unexpectedly and moves in with her, to her mounting dismay, but refuses to tell her why - then confesses to Caroline that she has left Annie's father. Annie demands a showdown with her father, who in turn confesses that this is no ordinary spat: he is in love for the first time in his life with another woman. Meanwhile, Richard takes a temporary job as a gift wrapper for Macy's, but his bad attitude gets him demoted to elf; and Del and Charley become convinced that their new assistant is a psycho killer, since all the people on her resume turn out to be dead.
When a doodle of a porcupine drawn by Richard gets into a stack of Caroline's greeting card designs by mistake, Del tries to convince Richard to develop the idea into a character of his own - but Richard protests that he is a real artist, not a cartoonist, throwing Caroline for a loop. Annie can't seem to shake a recurring five dollar bill with ""Repent"" written on it, and her mother tries to convince her it's a sign from God that she should return to the Church. When Caroline accidentally gets locked inside the laundry room overnight, her encounter with a bum who used to be a trucking magnate convinces her she has made the right career choice. Richard succumbs to Del's monetary temptation and produces a series of increasingly gloomy and unusable porcupine cards; and he finally apologizes and admits that he admires Caroline's professionalism as a cartoonist. Meanwhile, when a telegram stripper shows up at Del's office by mistake (she was supposed to be at a law firm), Del hires her as r
Caroline's romance is beached when Joe's ex returns from an environmental mission.
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.
Caroline's romance is beached when Joe's ex returns from an environmental mission.
Richard wins a chance to make his dreams come true by sinking a $100,000 three-pointer during a Knicks game.
It's not a pretty picture when Caroline persuades reluctant con-artist Richard to fake his own death in order to catch the eye of a wealthy art dealer who's scouring the city in search of the works of dead painters - and who winds up delivering the eulogy at Richard's fake funeral.
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.
Del hopes to spark up romance with Annie's neurotic friend Cassandra, who plans on lighting a fire of her own - she's a compulsive pyromaniac just of an institution. Meanwhile, Caroline spends a night out on the town ""alone,"" crashing the restaurant where Richard is trying to enjoy a quiet meal and ultimately being forced by him to attend a movie on her own. Meanwhile, Charlie keeps spotting monkeys throughout Manhattan, and becomes convinced they are taking over the city.
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.
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.
When Caroline learns that an obscure upstate newspaper has dropped her syndicated strip, she drives up with a reluctant Richard to find out why. Naturally Richard's car breaks down, and the two wind up playing marriage counselor to the only local mechanic and his on-the-point-of-leaving wife. Meanwhile, Annie recognizes an obnoxious diner at Remo's as the theater critic who gave her the worst review of her career, and hatches an elaborate revenge plot that involves Del, Charlie, and a cab driver/actor with his own ax to grind.
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.
Caroline and Annie are overjoyed to learn that Caroline's agent has arranged for her to promote her new book on the Jay Leno show; then Annie reminds Caroline that she will need an entertaining story to tell. Enter Richard's mother Natalie, carrying a jacket that belonged to Jerry Garcia and revealing that the dead rocker was Richard's real father. But Richard, hiding in the stairwell until his mother leaves, isn't impressed: there's hardly a celebrity that Natalie hasn't maintained fathered him. While Caroline and Annie fly to Los Angeles, Del tries to teach Richard how to pick up women during Happy Hour at Remo's (Richard: ""I'm not sure I can do that - I mean, be happy for a whole hour.""), and Charlie goes in search of his father, whom an adoption agency locates instantly: a bumbling waiter in a fashionable restaurant who is overjoyed to meet Charlie, even though their reunion gets him fired two weeks before his retirement. While waiting to appear with Leno, Caroline is warned that s
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.
Conclusion. Julia arrives at ""Richard and Caroline's"" apartment in tears, announcing that her engagement is over and demanding to spend the night on the sofa - which means Richard and Caroline have to spend the night together in her bedroom. A nude Julia reveals that seeing the happy couple has revived her feelings for a non-plussed Richard; meanwhile, Caroline consults Del about the possibility of a relationship with Richard, and an uncharacteristically thoughtful Del advises her to follow her heart. Annie's first day on the set of the Shadoe Stevens series doesn't go well, as she is totally unable to master her complicated medical lines, until the director and writer agree to switch her to the part of the hard-bitten female cop (resulting in even more unspeakable jargon). Del is in despair over the impending loss of his company, until Charlie bails him out with the trust find his father has maintained for him all these years - on condition that he becomes Del's partner. Caroline phon
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.
When Richard shows up wearing a ridiculous shirt Julia forced him to wear, Caroline advises him to talk to her frankly about the compromises inherent in marriage - and Julia leaves him. Meanwhile, Charlie is upset that Del still treats him as an underling rather than a partner, and Annie tries to cope with unemployment by finishing The Grapes of Wrath - which she started in eighth grade.
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.
Caroline's date reads more like a Shakespearean tragedy after she tells a lie to James, an attractive novelist she runs into during her book signing, and must then desperately cover for the fact that she hasn't actually read his novel; Richard tables his own remedy when Julia's job at Remo's is a disaster and he has to replace her as waiter; it's bad fortune for Annie when a fortune cookie leads Charlie to believe they share a recipe for love; and Del inadvertently becomes third party on a honeymoon.
Del gets excited over commercial possibilies when a civic politican mentions Caroline's cartoon strip in a speech, but Richard pours cold water on the idea: the man has a terrible record for opposing funding for the arts. His opinon changes slightly when Del drags the wily politico over for a meeting, whereupon Lake goes wild over Richard's recently completed painting and buys it. By the time Richard thinks better of selling his first work to a man he despises, Julia has already spent the money on a honeymoon trip to Hawaii; so Caroline steps in to prove she is not as politically naive as everyone assumes. Meanwhile, Annie, trying to cope with her cousin Jennifer who has dropped out of high school to find an acting career in Manhattan, goes ballistic when she discovers the girl has met a man claiming to be a movie producer who has promised her a role opposite Keanu Reeves - and sets out for the guy's hotel room to tell him off....
While they wait for Chinese takeaway delivery, Richard shows Caroline a family wedding ring he was planning to give to Julia, and soon after, the heirloom seemingly disappears from her apartment -leading Fong to accuse, and throw out, his delivery boy son Tim, who takes up residence in Caroline's living room. Meanwhile, Del and Charlie scheme to climb to the top of the Rockefeller Center Christmas tree to place a large ad for Caroline's line of holiday cards; and Annie develops a cabaret act and is attracted to hunky guitarist Paul, while oblivious to pianist Seth's growing infatuation with her.
Julia tries to cheer up Caroline by setting her up on a blind date, which Richard does his best to sabotage. Meanwhile, Annie prepares to realize her dreams of revenge at her high-school reunion, with an overly coached Del in tow pretending to be her highly successful husband.
Annie's former mentor from New Jersey is coming to town especially to see her star pupil in Cats, unaware that Annie quit the show. Annie begs Caroline to accompany them to dinner, where they learn that Miss McGowan has recently lost over 150 pounds, but immediately begins to overeat when Annie attempts to explain - so an uncharacteristically timid Annie must beg the producer for her job back for just one golden evening for Miss McGowan, abetted by an old programme supplied by Del. Meanwhile, Richard joins Charlie as an experimental guinea pig for testing new drugs (""We prefer the term biosluts.""), but a new antihistamine soon has them both convinced that Richard's furniture is staring at them.
Caroline's former colorist Jeannie comes back to town on a mission: she and her husband can't conceive, so she wants Caroline to donate an egg; Annie naturally seizes the opportunity to make Richard paranoid that Caroline plans to re-hire Jeannie. Meanwhile, Del has a close encounter with his old Porsche and gets himself hired as a male escort for the company that now owns his former automotive love.
An unusual episode focussing on Del, who for once has an adult problem after he hears some shocking news from Laura, a former fling who's in town for the weekend - together with the daughter she had by Del but never told him about. Torn between a burning desire to meet his child and his terror of being a total disappointment to her, and Annie's brother quits his job to become a painter after he misinterprets Richard's evaluation of his work as an artist.
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.
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.
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....
Annie's been dating Seth Rudetski for six weeks now, and he's decided it's time for her to meet his parents, an intellectual couple who run ""Nothing Trivial,"" a quiz show broadcast to colleges on public radio. They turn out to be big fans of Caroline's strip, and persuade her to appear as a celebrity contestant - a decision that revives her childhood trauma (seen in a flashback) of freezing under the pressure of a state spelling bee. While Del and Charlie try to coach her through her anxiety, she appeals to Richard - and Julia steps in with a solution of her own. Meanwhile, Annie's feeling pressure of a different sort: from the excessively close relationship between Seth and his doting parents. (.)
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.
In a surreal take-off on both The Outer Limits and The Twilight Zone, Caroline insists that Richard work late once too often for Julia, who accuses Caroline of being an inconsiderate employer and says that she should ""walk a mile in my shoes."" Caroline instantly finds herself doing just that, since everyone now sees her as Julia and Julia as Caroline, while (in the best touch) Charlie narrates a la Rod Serling. Caroline discovers the advantages of being the gorgeous Julia - the customers at Remo's don't care that she's an incompetent bartender so long as they get to ogle her behind her back - but is frustrated in her attempts to take advantage of the ""special thing"" Richard wants Julia to do with him as soon as they get home.
An ecstatic Annie bursts in on Caroline and Trevor to announce that her mother is finally moving out to live with an aunt in the suburbs. When Caroline discovers that Trevor has left his toothbrush behind, she begins worrying about whether their relationship is moving too fast, then decides to get a key cut for Trevor, then takes Annie's advice not to give it to him yet - only to discover that a distracted Richard has already done so. Both Richard and Caroline pursue Trevor to his gym, where they have to fend off the attempts of an over-motivated employee to sign them up as members and where Caroline and a flustered Trevor finally reach an understanding of sorts in the steam room. Meanwhile, Del and Charlie pursue their daftest promotional scheme yet: kidnapping the Central Park groundhog so that when he emerges he will be wearing a little Caroline in the City cape. Naturally, this scheme backfires, along the way ensuring that Annie's mother doesn't move out after all. (So now that she
Richard gets a chance to have a painting exhibited at the New York Public Library, but falls victim to on-line addiction at a cyber cafe. An outraged Caroline files a complaint against a rude cabbie, but Richard is her only witness (""A rude cab driver in New York? What's next, tall buildings?"") and fails to show up at the hearing. Meanwhile, after literal years on the waiting list, Annie finally gets an appointment with famous hair stylist Olaf, only to have Del and Charlie invade her session with a ridiculous scheme to market the hair sweepings of the famous - which Olaf loves.
Annie goes on a blind date with a former priest, and to her own surprise hits it off with him - particularly when she learns he has never been with a woman but would really, really like to be. Richard attempts to reconcile with Julia's multi-millionaire dad, who is still convinced that Richard is only after Julia for the money, and Caroline becomes convinced by a serious of strange accidents that he is actually trying to kill Richard: a theory Richard poo-poos until he finds himself at the controls of a plummeting plane while Mazzone prepares to parachute to safety. Meanwhile, Del thinks he can improve on the punch line of Caroline's latest cartoon, then he and Charlie desperately try to retrieve it from the syndication editors before it goes to press, using measures that give new meaning to the phrase ""cartoon strip.""
Annie comes in to Caroline's apartment to find Richard, Julia, Trevor, Caroline, Del and Charlie bound and gagged together - which turns out to be the doing of a deranged marriage counselor, as we learn in a series of flashbacks: To quit or not to quit? That is the question Richard faces in this hour-long episode. When Julia is finally able to claim her inheritance, the Karinskys move into a penthouse and ponder leaving their jobs. While Mrs. Karinsky gives up bartending in a flash, Richard makes excuses about abruptly leaving Caroline. A concerned Julia hires a marriage counselor, who turns out to be more interested in Richard's job than his life. Meanwhile, Caroline suggests that she and Trevor move in together. Garry Shandling has a cameo as one of the therapist's other patients.
Caroline and Jo Anne Worley agree to stage a feud after the cartoonist is blamed for having a deli sandwich named for Worley being renamed in her own honor. Meanwhile, Richard agonizes because Julia's regained wealth has given him painter's block; and Annie shows a reluctant Richard that his new $12,000 gold Rolex watch gives him shopper's credit in the stores that formerly scorned him.
When Caroline's mother visits, Annie becomes upset at the blandness of their relationship and encourages Caroline to have a healthy fight as she and Angie do. When Caroline timidly tries to open up to her mom, Margaret repostes with a real shocker: she hates Caroline's comic strip. Meanwhile, Del and Charlie go to Atlantic City at the request of a potential investor, and Richard tags along for the free ride, desperately trying to finish the new John Grisham thriller while resisting everyone's determination to tell him the surprise ending.
For insurance purposes, Del and Charlie pretend to be gay, but then Del meets a beautiful woman at a party, and in trying to pursue her gets himself and Charlie invited to be the couple of honor at a gay pride rally. Meanwhle, Richard reluctantly agrees to change his appearance so that he'll be picked for jury duty, and Annie lies to her mom about her dad's fiancée.
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
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
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
When Carol can no longer stand the pressure Del is putting on her to work out of her new corporate office instead of her home, a reluctant Caroline discovers that Richard has been sleeping there: his vengeful father-in-law has stripped him of apartments, possessions and credit cards, and Charley has been using Richard's old apartment as a makeshift hotel for visiting Russians. Then Richard falls afoul of the militaristic office manager Plum, who subjects him to standard employment tests, including a visit to the staff psychologist - who finds Richard's behavior a little odd.
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.
It's just not Annie's day: she gets fired from Cats after eight years and is immediately dumped by her agent. To get back some self esteem, she agrees to go out with her dry cleaner to his dry cleaners' annual banquet, but when she attempts to strut both their stuff on the dance floor, she succeeds only in fracturing his leg. Meanwhile, since sales of her greeting cards are down, Del talks Caroline into attending a focus group which some wild new ideas about Caroline's cartoon strip. Richard is aghast to find Caroline seriously considering some of them (turning Salty into a dog, giving Caroline super-powers); then Del announces that all greeting card sales are down, Caroline's less than most.
It's Halloween and Del is put in charge of the firm's Halloween party, only to find out that it is a sure-fire way to be sacked. Caroline and Richard go on their first date together but they have different ideas about what they should do.
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
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...
Jealousy between Richard and Annie reaches a new height when Richard wants to attend an operatic recital to which Caroline invited Annie months ago. The two squabble so childishly that an infuriated Caroline tells them off loudly - and the insulted diva walks off the stage and refuses to return. When Caroline sneaks into the star's dressing room to apologize and beg her to finish the recital, she winds up rubbing her feet and getting drunk with her on champagne, and returns home to find that Richard and Annie's mutual anxiety about her whereabouts has produced a sort of truce. Meanwhile, Del finds himself taking a reluctant ethical stance when he is invited to an executive charter jet weekend on condition that he persuades cartoonist Reg to introduce a white character into his black-only post-apocalyptic fantasy world; and a furtive pair of nerdish animators fall madly in love with Caroline but are unable to speak in her presence.
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.
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.
Richard, Del and Annie are apparently successful in their combined effort to knock the Christmas spirit out of Caroline, but when she appears to have lost all interest in her annual tree-trimming festivities, her alarmed buddies declare an emergency trip to nearby ""Christmasville,"" only to discover that Caroline engineered the whole thing. When even the local re-enactment of A Christmas Carol doesn't do the trick, a furious Caroline tries to drive away and backs into the town's main transformer, blacking out all of ""Christmasville"" and condemning them to slave off their sentence in Santa's workshop.
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.""
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.
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.
Caroline and the gang visit her family's home in Wisconsin and learn her parents are selling the house. Distraught, she prolongs her stay (while Richard unwillingly bonds with the locals), and ultimately decides to preserve her childhood memories by buying the house herself.
Caroline tries to right an old wrong by giving up a romantic weekend in Boston with Richard to help out a visiting childhood chum, Joanie, whom Caroline once bullied in school. Meanwhile, a lonely Annie finds unexpected companionship with a smooth-talking parrot when she agrees to bird-sit for Dave, and Del has trouble accepting the fact that his new girlfriend Lisa is taller than he is.
There's to be a big celebrity banquet to celebrate Caroline's 2000th strip, but there's a snag: Caroline is completely blocked in terms of fresh, funny ideas. While everyone else waits for her to get ready (Richard in a cheap rental tuxedo which gradually disintegrates), Caroline fantasizes about what life would be like if she retired. When she tearfully refuses to attend the banquet and does laundry instead, Richard gently points out that she has stopped writing about her real life in the strip (her fictional counterpart is ""still dating that veterinarian"") and perhaps it is time to bring her readers up to date -- and Caroline immediately draws a strip about their first date on the side of the washing machine.
Caroline's plans to rent out her house in Wisconsin hit an unexpected snag when Grandma Duffy refuses to leave, forcing Caroline to return to Wisconsin, where she is surprised to learn that her former boyfriend Randy will be her new tenant. Meanwhile, Richard has his hands full in New York when he agrees to take Caroline's place by caring for Annie (who is sick) and Del (who thinks his girlfriend may be cheating on him).
Sparks fly between Caroline and Randy when he pays her a surprise visit in New York and they end up getting stuck together in a subway tunnel for two hours. Meanwhile, Richard gets his first real break as an artist when an eccentric gallery owner offers to exhibit his work -- but only if he can create another 'bleak' painting in time for the next day's show.
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.
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.
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...
