Ruth and Pauline try to help save a friend's failing bookstore by annexing it to the Flower Cafe.

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.

A strange woman comes to the shop under the impression that Hilton is her husband, Charlie.

Hilton is overjoyed when he meets new friends Chuck and Larry and joins their ""Older and Out"" team, since he's also older and he's ""out"" keeping busy. Ruth discovers that Chuck is gay, and she mistakenly believes that her husband of more than 30 years may have feelings for a man! Blaming herself for letting the spark go out of the marriage, Ruth sets off to win him back before a surprised Hilton discovers the real meaning of ""Older and Out.""

Hilton is shocked to find out that an antique store where he has a new job is really a front for illegal activity: a brothel the police are planning to raid. When the cops want Hilton to help put the criminals out of business, he overeagerly accepts the challenge to do his duty as an American citizen and take part in their ""undercover sting operation."" Meanwhile, he is sworn to secrecy about his assignment and is therefore unable to stop Ruthie from spending the paycheck he knows he will never receive.

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.

Darien's late arrival to an important family dinner causes a fight between Hilton and Ruth.

Downsizing at the airport forces Hilton to retire.

Deceit weaves a tangled web around Hilton, who tells ""one little lie"" and then, to keep up the ruse, finds that he must pretend he's someone else -- and not married to Ruth. In order to avoid attending a wedding, Hilton fibs about needing brain surgery -- and pays a high price. Hilton is always frustrated by everyday deceits, including truth in advertising. Nevertheless, he makes up the lie to avoid attending the Sunday wedding of the son of Ruth's friends, Elaine and Dave, which interferes with his watching sports on television. Pretty soon, he's ensnared in a tangled web of his own making..

Hilton discovers that a former high school buddy is now homeless.

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. The coffee shop hosts it's first poetry night.

Hilton is bequeathed a boat by a wealthy man he once helped at the airport. Despite Ruth's insistence that he doesn't have the stamina or the money to support a boating hobby, Hilton persists -- including spending three days on the boat with Griffin, parked outside the house in the freezing cold.

When Griffin tries to prepare for Y2K by installing a generator, he causes a premature blackout for the entire neighborhood.

The cast presents a heartfelt tribute to Madeline Kahn, with clips highlighting her character Pauline.

When Ruth teaches Erica how to play golf, a rivalry begins between the two women that even extends to cooking.

Griffin's inablity to deal with the return of his estranged father, who abandoned him 15 years earlier, causes problems in his relationship with Rebecca.

Hilton suffers from insomnia for several days, falling asleep during the day at inopertune moments, causing Erica and Ruth embarassment. When Hilton refuses to attend a sleep clinic, Griffin offers to set up a video camera in the Lucas' bedroom to record the night's activity to find the cause of Hilton's sleeplessness. The next morning, when the family gathers to watch the tape, no one is more surprised than Ruth to see that it's her snoring and kicking Hilton in her sleep that keeps him awake.

Griffin is helping Hilton fix the bathroom door when Wendy arrives very upset and looking for Pauline, her godmother. Before she leaves Hilton has given her $45 to help pay her overdue phone bill. Later Pauline learns that Wendy is in debt for over $15,000, and she's determined to teach Wendy some fiscal responsibility, and she tells Hilton it will be a long time before he sees any of his money. Hilton goes to the bank and learns that not only has his bank has merged with another bank, but also that the computers are down and he can't withdraw any money. After a long, frustrating wait, Hilton uses the ATM machine outside the bank, and, instead of the $50 he requested, the machine gives him $11,000. Hilton is tempted to take the money and run. When Ruthie comes home, Hilton expects a compliment for fixing the door, but instead she discovers a huge scratch that Griffin has made in the wall. When Ruthie learns about Wendy and all her debts, she says she'll forgive the scratch in the wall

Hilton tries to convince the Social Security Administration that he is not dead.

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

Griffin has a dream in which teachers are given the same elite status & salary as professional athletes or actors.

Hilton finds himself in the middle of a Bank Heist.

It's Valentine's Day, and when Hilton realizes that he has bought Ruth a scarf that she already has, it's back to the drawing board. When she mentions that she'd love to see singer Jeffrey Osborne, who's appearing at the Steinway Club that night, a desperate Hilton says that he has tickets and was going to surprise her. Since Valentine's Day is a very busy day at the flower shop, Hilton tries to help Ruth and Pauline, but he buys the wrong flowers at the flower mart and causes the delivery truck to be towed. Ruth refuses to get angry with him because she thinks he's taking her to see Jeffrey Osborne. Hilton is at a complete loss, when Griffin realizes that Charlie, a buddy of his, is a waiter at the club, and maybe he can get them in. Hilton and Griffin arrive at the club just as Charlie is being fired; Hilton pleads with Jack, the abrasive club owner, but Jack not only laughs in his face, he bans him from the club. At that point, Hilton's temper flares; he tells Jack off and storms ou

Pressed by Ruth to address his ""unusual behavior,"" Hilton enters group therapy. Bad idea. Now he misbehaves by counseling an old crony, who promptly loses his job.

By chance, Hilton brings Erica's freshly baked chocolate chip cookies to the struggling flower shop for Ruth and Pauline to enjoy and, just as he's setting out the coffee, strangers approach and ask to buy the goodies. This gives Hilton an idea and, much to Ruth and Pauline's dismay, he invests in a super-deluxe, super-expensive espresso machine, forces Erica to wake-up in the middle of the night to bake cookies, and turns what was an ordinary florist shop into The Flower Cafe.