After Hilton encourages Erica and Griffin to "take risks and pursue their dreams," they do just that and the results become Hilton's nightmares. Erica quits her high-paying job at the law firm, and moves home to save money and study to become a chef. Griffin, on the other hand, moves into the Lucas attic after a business deal goes wrong.

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By chance, Hilton brings Erica's freshly baked chocolate chip cookies to the struggling flower shop for Ruth and Pauline to enjoy when, just as he's setting out the coffee, strangers ask to buy the goodies. This gives Hilton an idea and he invests in a fancy espresso machine, forces Erica to wake-up in the middle of the night to bake cookies and turns the flower shop into the Flower Café.

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When Hilton realizes that Griffin and Erica's friends are taking over his house by watching his television and eating all his food, he decides that if they live in his house, Griffin and Erica will have to live by his rules.

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Sparked over once again butting heads, Griffin and Hilton make a deal; Griffin cannot eat anything for 24 hours, and Hilton can not give his opinion for 24 hours, which becomes harder as temptations are suddenly thrown Hilton's way, including Pauline's new boyfriend, a Federally-funded "performance artist" known as "Donald".

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Hilton is overjoyed when he meets new friends Chuck and Larry and joins their "Older and Out" team, since he's also older and "out" keeping busy. Ruth discovers that Chuck is gay and she mistakenly believes that her husband of more than thirty years may have feelings for a man.

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Pauline is absolutely thrilled that, after years of being the single friend, she has finally become a couple with her new boyfriend Gregory, a self-absorbed, self-proclaimed genius who disturbs Hilton. When she decides to dump him because he's too uptight, Ruth thinks that Hilton is really the one to blame and sends him off to remedy the situation.

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A doctor places Hilton under strict quarantine after he catches the stomach flu. Griffin warns Hilton not to escape quarantine, but he doesn't listen and, one by one, everyone in the household drops, leaving Hilton to don his nurse's uniform.

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When Ruth's snobbish sister-in-law Debra throws an engagement party for her daughter, Hilton and Ruth try to steal some of Debra's thunder by arranging for Erica to bring a handsome date to the party, but they get some unexpected results.

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When Griffin tries to back out of a lucrative out-of-state concert gig because of a flying phobia, Hilton vows that he will get Griffin on the plane no matter what it takes.

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Frank Barone has been telling his son about sinking the winning shot in the 1955 Queens basketball championship since the day he was born. When Frank pleads with Hilton to help him save face with his son by lying for him, Hilton reluctantly agrees.

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Ruth surprises Hilton when she enrolls him in tap-dancing classes as a birthday gift. He skips the classes, but tells Ruth that he is making remarkable progress. When Ruth announces that she is going to attend the dance recital, Hilton must take a crash course in fancy footwork or risk having his deception exposed.

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Hilton and Griffin get jobs as telemarketers, hoping to win a fabulous office prize - a weekend for two at the Plaza Hotel in Manhattan. Hilton is afraid to tell his wife, knowing she will disapprove of his new job. Instead, he lies and claims that he's now driving Danny Aiello's limo.

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Ruth must deal with a bunch of know-it-alls. Hilton firmly believes that his community center boys' basketball team could beat her girls' team. When Ruth challenges Hilton and his team, he has a lot to do to get his star players in shape. Meanwhile, Ruth must teach Nikki, one of her players, the importance of teamwork.

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Pauline and Erica want to take Ruth to a spa for a weekend of pampering while the café is closed for maintenance. While they are away, Hilton is in charge of the coffee shop. Carla, the chaperone of a Brazilian girls' choir, offers Hilton $500 to rent the café for a private party for the college seniors. Hilton hesitates, but the money is too enticing to resist.

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Despite Ruth's insistence that family and friends should never work together, Hilton goes to work for Griffin, narrating children's stories. He just can't refuse the temptation for some creative rewriting, and Hilton puts his own spin on some classic kids' tales. Will he have his poetic license revoked?

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A wealthy man Hilton once helped at the airport bequeaths him a boat. Despite Ruth's insistence that he doesn't have the stamina or the money to support a boating hobby, Hilton persists.

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While at work at the Coffee Shop, Hilton meets Rob Burnett and Paul Shaffer from the "Late Show with David Letterman". Hilton then inquires about being booked as a guest on the Late Show.

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With Ruth's birthday coming up, Erica suggests that Hilton buy her something other than a sweater, which has been his gift every year for the past ten years. In an attempt to be more original, Hilton paints a plate for Ruth at a pottery store.

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Pauline tries her hand at playwriting for a course she's taking at the community center. Following Hilton's advice about writing something "real," she turns out a thinly-disguised comedy about the Lucas family.

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It's April 15th and Hilton hasn't even started working on his taxes, a fact he wants to make sure Ruth doesn't discover.

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Erica and her girlfriends, unable to find "Mr. Right," take Ruth's advice about changing their dating habits and set out on "The Great American Manhunt."

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When Ruth and Hilton have a major fight, they assess the changes in their lives.

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The Lucases play Cupid for smitten Griffin.

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Ruth has been elected the first woman president of the Astoria Businessmen's Roundtable, which automatically makes Hilton the head of the women's auxiliary.

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