Hilton's new responsibility, looking after 11-year-old Jurnee while her dad is at work, becomes a little too hot to handle when Jurnee asks him a complicated question about the birds and bees. Not wanting to interfere in Jurnee's upbringing, and looking for a way to avoid having to answer himself, Hilton suggests that the curious Jurnee go to her dad for an explanation. No matter how difficult it is for Del to face the fact that Jurnee is growing up (perhaps a bit faster than he had hoped), with coaching from Hilton, he finally appears ready to have ‘the talk.'

Griffin and Erica work out a financial deal to move into Griffin's house on a landlord-tenant basis -- thus giving Hilton and Ruth back their privacy – only to have Griffin's house accidentally burn to the ground. Hilton's visions of spending romantic evenings alone with Ruth are over before they've even begun. And, when Erica and Griffin realize that everything destroyed in the fire was either borrowed, rented or on loan, they decide it's time to grow up and start taking ""ownership"" of their lives.

Hilton is devastated to learn that Erica is breaking up with her latest boyfriend, Gil -- a handsome, well-educated jazz musician who is everything that Hilton could ever want in a guy and more. When Erica and Gil mutually decide to call it quits, it's Hilton who takes the news the hardest since he's developed his own meaningful relationship with Gil -- primarily because he represents the jazzman Hilton always wanted to be. How will Hilton go on? All he does is sit by the phone and wait for Gil to call! It's true that break-ups can be hard -- but usually for the two people involved.

Petty differences about irritating personal habits threaten to escalate into a major brawl when Ruth and Pauline plan a ""girls' night out"" in Manhattan, and Hilton insists on acting as their chauffeur

A major argument erupts when Ruth accidentally discovers that Erica has been hiding all the gifts she has given her over the years. When Ruth confronts Erica about only pretending to like the gifts that Ruth put so much time and care into buying, it sparks the disagreement. On the one hand, Ruth feels that she doesn't know her own daughter, and on the flip side, Erica feels that her mother doesn't bother to learn about her likes and dislikes. Although Hilton desperately wants to stay out of their argument, he is left with no alternative and attempts to coerce the women into a joint shopping trip. The goal -- buy something that is pleasing to them both without driving him over the edge.

After Jurnee expresses her fondness for schoolmate Kevin and he retaliates by shoving her on the school playground, amateur psychologist Hilton explains his theory of how ""playground scarring"" can affect a woman for life. According to Hilton, when women are unable to trust, unable to commit, their problems can always be traced back to a bad playground experience when they were deeply humiliated by a boy they liked. To this day, Ruth has problems with trust because of a certain Kenneth P. Watson, who purposely teetered when he should have tottered, requiring a young Ruth to get stitches. When it comes to Jurnee, however, Hilton is determined not to have history repeat itself.

Hilton is sentenced to a life without pork chops, barbeque ribs and bacon when a doctor's visit reveals a too-high cholesterol count. A mouth-watering meal for Hilton now consists of tofu, steamed broccoli and ""not-wurst"" imitation hot dogs. New Jersey Nets player Jayson Williams guest stars as Jurnee's teacher, who adds his two-cents on the subject of of Hilton's eating habits.

Hilton's steaming when a klutzy customer spills coffee on her dress, admits it's her own fault---and then sues the Flower Cafe for $3000.

When Hilton offers to make Jurnee's Thanksgiving Day Parade turkey costume from scratch, it comes out to be just that.... a turkey of a costume. So imagine Hilton's joy when the queen of domesticity, Martha Stewart, shows up at the coffee shop bearing the most realistic looking turkey outfit that anyone's ever seen and leaves it behind by mistake. But, when Martha Stewart returns asking if anyone has seen the costume, will Hilton's guilt get the best of him... or will Jurnee be the best-dressed turkey in the parade?

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Del's new girlfriend Karen agonizes over a secret she's worried about sharing with him: the youth who passes as her kid brother is actually her son.

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Griffin contemplates quitting the teaching profession when his first day as a substitute teacher is a disaster. The Lucases lend themselves out as mock students so that Griffin can practice his teaching techniques on them -- although their misguided attempt to help might just turn him off teaching forever.

After the Lucas home is burglarized, Hilton invests in a security system -- only to discover that the thief is someone he knows.

Hilton and Ruth recall their first date many years ago. Their flashbacks are done through animated sequences, and of course, both of them have widely different versions of what happened.

While searching for a rare part for his beloved turntable, Hilton bumps into an old friend from his bachelor days, Fred. When Hilton and Fred start reminiscing about how they double-dated sisters Mattie and Roberta Singleton, Hilton decides to play matchmaker and prompts Fred into learning whatever became of Mattie. Even now, years later, Fred can't help wondering what might have happened if they remained a couple.... and, thanks to Hilton, he may finally get a chance to find out.

Jurnee is aghast when she finds out that her dad intends to date the ""meanest"" teacher at her school. Del is so troubled by Jurnee's reaction to his interest in Ms. Malone that he's ready to call off their date. But Hilton reminds him that almost every person can remember a teacher who was too strict, gave too much homework or expected too much of a student -- and usually ended up being the one who made the greatest impact on the student later in life.

Hilton is attempting to help Jurnee with her ""Romeo and Juliet"" homework assignment when his true feelings about The Bard come out: Why couldn't Shakespeare simply speak in plain English rather than using all of that fancy, confusing language? Alas, Shakespeare showeth up in the Lucas kitchen to tutor Hilton personally. Will it be ""all's well that ends well?""

Hilton volunteers as a reader for a retired, blind English literature professor and, upon realizing his gift for teaching, urges him to return to the classroom. Anthony Quinn guest stars as Professor Christo, whose failing eyesight and advanced age caused him to leave behind the profession he loves so much.

Hilton is caught in the middle when his curmudgeonly friend, Tim, stages a rent strike against his landlord.

Hilton is stunned when 11-year old Jurnee, left in his care while her father is away, returns from a friend's birthday party drunk. Hilton and Ruth are adamant about finding out who spiked the birthday punch and caused several of the children to awaken to wicked hangovers the following morning. But, Jurnee is not budging for fear that she will be labeled a squealer among her friends. Hilton is determined to make Jurnee understand that protecting the guilty person is sometimes just as bad as being guilty yourself.

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When Hilton and Ruth hear that their ""little girl"" is getting married, they couldn't be happier for her, or themselves, since this would mean one less person in their crowded house. Erica's intentions, however, are for the newlyweds to remain in her parent's house indefinitely to save some money. Are Hilton's tears of joy or sorrow?

Griffin's trust in his new girlfriend Anita is put to the test when her job as a conference planner puts her smack in the middle of a young millionaires' convention, on the season finale. Rather than heeding Hilton's advice to give Anita some space, Griffin decides to pop in on the convention and find out for himself how loyal Anita is -- which prompts Hilton to reminisce about the anxious time he spent away from Ruth, soon after they first met, agonizing over whether or not she was thinking of him as often as he was of her. ""Prequel Monday"" kicks off with an animated flashback sequence of Hilton as an enlisted Navy man.