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After Richard's divorce he can finally be together with Caroline. Del was forced to sell his company Eagle Greeting Cards which was taken over by big publishing company and at the end Caroline and Richard were forced to move to company office building.
In second part of the season Caroline takes trip to Peshtigo where she meets her school friend Randy, who shares her Midwest approach to life. She gets confused in her feelings especially when Richard is concentrated more on his career than their relationship. Annie after being fired from Cats is desperate in finding a new job.
The fourth-season opener finds Caroline and Richard savoring their first passionate kiss and preparing for romance. But the moment is spoiled when Caroline gets a series of unexpected visitors - some real and some imagined -- and even more unexpected news regarding her future with Eagle Greeting Cards.
Guest stars: Richard Kuhlman as Ken, Scott Ferguson as Dennis, Joey Zimmerman as Chuckie, Sean Moran as Janitor,
Vengeful father-in-law Mr. Mazzone strips Richard of all his worldly possessions, forcing Richard to take temporary refuge in Caroline's new office, where he runs afoul of Plum, the no-nonsense office manager. Meanwhile, Caroline finally succumbs to Del's pleading and agrees to come work in the corporate office - unaware that Richard has spent the night there.
Guest stars: Nancy Lenahan as Plum, Charles Cioffi as Mr. Mazzone, Paul Willson as Dr. Bernstein, Joel McCrary as Max,
After Caroline inadvertently offends office manager Plum, she and Richard are banished to a damp, dark basement office. While Caroline attempts to make peace with the feisty Plum, Annie tries to control her libido when she and her mother, Angie, take yoga lessons from a sexy instructor.
Guest stars: Candice Azzara as Angie Spadaro, Nancy Lenehan as Plum, Adrian Zmed as Jonathan, Doris Hess as Betty, Marc Goldsmith as Marc,
After Annie loses her boyfriend, her job and her agent, she impulsively accepts a date with her local dry cleaner, Gil, and spends an evening to remember. Meanwhile, Del organizes a focus group to determine why Caroline's greeting card sales are down and, much to Richard's dismay, Caroline takes their off-the-wall suggestions to heart.
Guest stars: Ken Campbell as Gil, Jeff Doucette as Duane, Carlos LaCamara as Mark, John La Motta as focus group man, Casey Williams as focus group woman, Steve Nevil as announcer, Vanessa Lock as Toni, Yuria Kim as Korean Woman,
Caroline and Richard decide to go out on their first official "date" together on Halloween, but their romantic evening turns into fright night when Richard gets himself into a rooftop jam. Meanwhile, Del agrees to organize the office Halloween party, then is terrified to learn that his boss has a history of firing every executive who's been put in charge of the ghoulish festivities.
Guest stars: Edmund L. Shaff as MacDermott, Clint Carmichael as Zorro, Jane Lynch as Hostess, Rich Hall as Monster, Donna Ponterotto as Bride of Monster, Tony Edwards as Mr. Sampson, Chaz Monet as Princess,
Caroline's curiosity gets the best of her when she stumbles across Richard's divorce papers in his desk drawer, but an office mishap sends her on a frantic paper chase to retrieve the documents after they are lost in the interoffice mail. Meanwhile, Del coerces Charlie and Richard into helping him with a sock puppet demonstration of his proposed educational video on the female body.
Guest stars: Edmund L. Shaff as MacDermott, Robert Clndenin as Dave, Peter Paige as Robert, Mark Costanzi as Mailguy,
Caroline and Richard's relationship reaches a pivotal turning point after three years when they finally decide to consummate their relationship. But after checking into an old-fashioned inn for their first evening together, Caroline's romantic fantasies are dashed when their suite is mistakenly given to two other lovebirds, and they are forced to stay in a room with no bath. Undeterred, Caroline convinces Richard to sneak into the other couple's room for a candlelit rendezvous in their oversized tub, but their passion is dampened when the plan springs a leak.
Guest stars: Veanne Cox as Alice, Todd Waring as Steve, Richard Herd as Barney, Maree Cheatham as Dorothy, Greg Delisle as Saleswoman,
Caroline invites Richard and Annie to the opera, then hits a low note with a temperamental soprano after she inadvertently disrupts the diva's performance. Meanwhile, Del is handed the difficult task of asking a cartoonist, Reg, to "lighten up" his comic strip about post-apocalyptic Harlem.
Guest stars: Natalija Nogulich as Kay Reynaldo, Gregory Itzin as Hank, Reginald Ballard as Reg Preston, Phil Lord as Bill, Chris Miller as Cliff, Arnie Burton as House Manager,
Tired of losing acting roles to other, more well-endowed women, Annie surprises the gang on Thanksgiving Day by announcing that she plans to get breast implants. But the biggest shock of all comes when Caroline decides to join Annie at the doctor's office and fantasizes what life would be like with a bigger bosom. Meanwhile, Richard contemplates making his own cosmetic change as well.
Guest stars: Robert Clendenin as Dave, Kip Gilman as Dr. Forsythe, Rose Blasi as Lana, S. Marc Jordan as Frank, Joel Hollis as Pilot, Laura Lee as Stewardess, Christopher Grove as Economist, Kim Delgado as Coach Man, Jennifer Aquino as Nurse, Celeste Weaver as Heather,
Richard gets an offer that his empty bank account can't refuse: his Aunt Frieda promises to give him $5,000 as a Bar Mitzvah gift if he agrees to finally go through the ceremony. But his plan to quietly cash in is exposed when Aunt Frieda spills the beans to Caroline, who tries to make Richard feel guilty by offering to throw him a lavish Bar Mitzvah party. Meanwhile, Del also pays the price when he splurges on expensive Italian suits that are too tight for comfort.
Guest stars: Carol Locatell as Aunt Frieda, Barry Gordon as Rabbi Katz, Fred Applegate as Accordion Player, Phil Lord as Bill, Chris Miller as Clifff, Shia La Beouf as Ethan, Alfred Dennis as Sid,
Tired of being the brunt of their holiday jokes, Caroline tricks Richard, Del and Annie into taking a road trip to "Christmasville" to help them recapture their Christmas spirit. But when their rental car accidentally knocks out the town's power, Caroline and her friends are forced to make amends by working as elves in Santa's Workshop, where they toil at the mercy of the Scrooge-like Sheriff and a whip-cracking elf, Floyd.
Guest stars: Jerry Hardin as Sheriff Dohdig, Michael McShane as Boo, Cork Hubbert as Floyd, Ian Meltzer as Byron,
Richard agrees to let Reg become a houseguest after the cartoonist has a fight with his girlfriend, Wanda. But the arrangement soon causes a rift between Richard and Caroline when he allows Reg to remodel the apartment, but refuses to accept a simple bath mat from Caroline. Meanwhile, after Annie and Del join a health club to meet new people, Annie's social life gets an immediate pick-me-up from an Arnold Schwarzenegger-type who likes to flex his muscles by lifting heavy objects.
Guest stars: Roland Kickinger as Lars, JoNell Kennedy as Wanda, Warren Sweeney as Copier Man, Kelly Haren as Kelly, Shanna Igoe as Cheryl,
Caroline and Del experience mixed results when they become office mentors to a young cartoonist with an overactive libido and an eager marketing student with a knack for cleaning up Del's messy social life. Meanwhile, Richard pursues his dream of becoming a successful painter by holding his first exhibition at a local coffee house, and Annie auditions for a part that consists of only one line.
Guest stars: Brendon Ryan Barrett as Stan, Dale Godboldo as Hairbrush Guy, Christopher Michael Moore as Man, Mark Chaet as Mr. Muchakis, Drake Bell as Rodney, Jesse Stock as Hooter, Michael Dempsey as Auctioneer, Leslie Harter as Kelly,
Caroline tries to take Charlie under her wing and teach him the fundamentals of life - such as how to wear shoes - after Del is forced to fire the hapless in-line skater from his job at the greeting card company. Meanwhile, Caroline smells something fishy when Richard recommends Annie for a modeling job as a new animated character called 'Princess Neptuna.'
Guest stars: Lauren Katz as Shari, Sean Moran as Lonnie, Scott Lowell as Carl, James Henriksen as Robert, Eileen Barnett as Angela, Dierdre Holder as Nurse,
Caroline and the gang visit Caroline's family home in Pestigo, Wisconsin, but the homecoming is ruined when her parents tell Caroline that they are selling the house. Meanwhile, Richard tries to make friends with the Duffys' rambunctious young neighbors, while Del loses his luggage and is forced to wear Grandpa Duffy's clothes, and Annie gets hooked on watching 'Mannix' reruns with Caroline's dad.
Guest stars: Edie McClurg as Margaret Duffy, Earl Holliman as Fred Duffy, Kathleen Freeman as Grandma Duffy, Robert Alan Beuth as Realtor, Robert Rigamonti as Mr. Hess,
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.
Guest stars: Kelly Coffield as Joanie, Robert Clendenin as Dave, Monika Schnarre as Lisa,
Caroline draws a blank while trying to create her 2000th comic strip, and her anxiety provokes an imaginative series of vignettes depicting what her life would be like if she wasn't a cartoonist. In her fantasies, she becomes a free-spirited painter, a world traveler and, finally, a chorus line dancer who is magically joined on stage by Richard, Annie and Del in a rousing musical production of 'Sweet Charity.'
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.
Guest stars: Kathleen Freeman as Grandma Duffy, Judith Drake as Esther,
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.
Guest stars: Nike Doukas as Regina Abbott, Vince Melocchi as Passenger,
Caroline gives Richard a 7 p.m. deadline to make a marital commitment to her, then is coerced into spending the day making pottery with Del and Annie while she anxiously awaits his decision. Meanwhile, Richard receives some unsolicited advice from a video storeowner after they are locked up together in the store's back room by a bumbling robber.
Guest stars: Pat Morita as Mr. Chu, Meredith Autry as Cindy, John Ducey as Billy, J.P. Manoux as Customer, Gary Simpson as Paramedic,
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. Caroline also gets an unexpected visit from Randy, and Annie and Del flirt with the idea of having a no-strings-attached fling.
Guest stars: Edie McClurg as Margaret Duffy, Earl Holliman as Fred Duffy, Ron Orbach as Mike, Lisa Passero as Signora Fabiana, Barbara Brownell as Saleswoman, Gary Simpson as Paramedic, Bob Shauger as Man,
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. Meanwhile, Annie and Del begin a clandestine relationship. Flashing forward six months later, the season finale finds Caroline headed to the altar with Randy, when an unexpected guest arrives during the wedding ceremony.
Guest stars: Edie McClurg as Margaret Duffy, Earl Holliman as Fred Duffy, Lisa Passero as Signora Fabiana, Robert Bock as Minister,
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