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.

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...

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 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.

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.

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.

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.

Julia and Richard's marriage counselor starts work as Richard's replacement but finds that everyone still wants him to give them relationship advice.

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.

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.

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 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.

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).

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.

Realizing Caroline never received his love letter, Richard labors to retrieve it from her friend's apartment.

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.

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.

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.

Caroline returns home to find Richard, Julia, Trevor, Annie, 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'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.

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

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.

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.

Upset that Caroline's strip is not being merchandised aggressively, Del finally stands up to his father who promptly replaces Del as president with his sister, who in turn immediately fires him. Excited about forming his own company (with Charlie as his sole employee), Del assumes that Caroline will jump ship with him, particularly as he kept forgetting to renew her contract with his father's company. When Del calls his former cartoonist clients to a meeting in his crummy new office, they promptly desert him, leaving Caroline in the lurch how can she tell Del she values her income more than their friendship? Meanwhile, Richard is excited about being chosen to paint a mural for the city, even when he discovers he was the only applicant, but he's not prepared for the hostile reaction by the local denizens of the 'hood in question. He finally wins them round by agreeing to incorporate both Dennis Rodman and one hood's girlfriend into the mural, and even Annie is impressed at the unveiling