Ted decides to give Casey, his bride-to-be, a surprise wedding gift - a reunion with her long-lost father, Leo. Ted doesn't realize, however, that his bride cannot tolerate her father. Ted doesn't really understand this attitude because Leo is nothing like his own father, George, a quiet bookstore owner. Leo, a small-time hoodlum and part-time magician, can't go back to Las Vegas because he kept the last payoff he collected. Soon enough, a hit man arrives at George's home to collect the money. Leo's this close to getting whacked until George intervenes. The mob's on hold for now, but that's the least of George's problems because, on his way to the ferry, Leo happens to notice the spare room above George's bookstore. . . .
George is so desperate to get Ted and Casey married that he turns to Leo for help. Minutes before vows are to be exchanged, Casey's mother decides to tell her the real story behind her brief marriage to Leo, which so discourages Casey she goes running from the altar. George, who is even ready to accept a roller-blading priest to get the deed done, has to turn to Leo, a one-man fidelity wrecking crew, to set things straight.
When the Edgartown building inspector discovers that Leo is living above the bookstore, he threatens to fine George for violating a zoning ordinance. Leo convinces George to slip the inspector an envelope full of cash, which lands George in jail. George clumsily attempts to bribe a public official and lands in jail. When the Edgartown building inspector discovers that Leo is living above the bookstore, he threatens to fine George for violating a zoning ordinance. Leo convinces George to slip the inspector an envelope full of cash, which lands George in jail. Meanwhile, Casey and Ted don't know how to fire an incompetent waiter.
Leo and George enrol in a baby care class in an attempt to ready themselves for grandfatherhood, but their first assignment leaves them sifting for ways to reverse their troubles when their ""baby"" — a flour sack — has an accident. Leo wants to prove to Casey that she can count on him to babysit, so he enrolls himself in a baby care class, dragging George along as well. The two men are by far the most unusual couple in the class, and their first assignment is to care for a 10 pound sack of flour as though it were their baby. Unfortunately, the ""baby"" accidentally rolls off the roof of Grandpa George's car, and he and Leo then concoct a scheme to get a new ""baby,"" hoping no one will know the difference.
In order to prove to Ted and Casey that he'll be a good grandfather and help out financially when their baby is born, Leo ""borrows"" some of George's things and takes them to a pawn shop. When this scheme doesn't work, Leo lands a job in the restaurant industry - working a drive-through window dressed as a crustacean. Meanwhile, the islanders misinterpret the live-in relationship between George and Leo, but their open-mindedness helps Bob sell more books. An angry George kicks Leo out after catching him pawning items from the bookstore, but when he discovers that Leo was putting the money towards a trust fund for the baby, he relents and tracks him down to apologize.
Consoling with a dash of overkill is on the menu when a food critic pans Ted's restaurant, prompting Father Rick and George to serve up their own recipe on compassion; Leo finds that bargain basement prices aren't necessarily a good thing when it comes to apartment hunting. When his restaurant receives a bad review, Tedbecomes even more aware of his insecurities — and of George's inability to say that he's proud of his son. Meanwhile, Leo rents an apartment next to a lighthouse.
A grab bag of fears makes Halloween night on the Vineyard a real scream. It all starts with a ghost story told by Ambrose at the bookstore, which leaves a superstitious Leo convinced he's not the only one haunting the place. Meanwhile, George faces his annual fear: running out of Halloween candy and incurring the wrath of angry trick-or-treaters. And Ted and Casey, afraid for their sanity after spending too much time together, decide that Casey needs some R&R. But when she retreats to The Harbor Inn, her respite is disturbed by a group of pro wrestlers — and by some other unwelcome intruders. When several books mysteriously disappear and lights begin to turn themselves off and on, Leo is convinced that the ghost of Rumsey Reeve, the headless sailor, has come back to haunt the bookstore. Meanwhile, George stocks up on generic candy, since he's heard that the neighborhood kids take the expression ""trick or treat"" very seriously. Unfortunately, a nervous Ted eats all the candy, leaving Ge
Cameos by actors from Newhart, Taxi, The Bob Newhart Show and Dear John highlight this bizarre episode which opens with a charity auction during which George wins a group-therapy session and Leo wins a van. George reluctantly visits the therapist and ends up working wonders on the group with his straightforward advice. Meanwhile, Leo uses his new van to run a taxi/tour-guide service and picks up a group of tourists who look strangely familiar. His passengers soon realize that Leo doesn't know the island very well and they are being taken for a ride.
George's new housekeeper Margie turns out to have boyfriend problems. He offers advice, and she so appreciates his support that she moves in with him, much to the delight of his nosy neighbors. Unfortunately, the girl's family isn't quite so excited, and George's joy over his young, beautiful and meticulously neat housekeeper is short-lived, after Leo has a miscommunication with the girl's overprotective dad. Meanwhile, Leo, in an effort to help Ted, becomes the restaurant industry's worst food buyer.
Secretive Sheila shows up one day in the bookstore, and George is somewhat stunned when she asks him out on a date. So is Leo, because he can't shake the nagging feeling that he and Sheila have met before. George's date is cut short when Leo finally remembers the shocking truth about Sheila and an old chapter in his life.
For years, George has hosted the same old (boring) Thanksgiving dinner. This year, with the addition of Leo, the party is suddenly festive - for everyone but George. Leo starts by flirting with George's beloved niece, Martha and their subsequent fling nearly drives George over the edge. Meanwhile, the sibling rivalry that Ted has nurtured for years is in full activation when his brother, Chip, shows up in his new Lexus.
Leo is a steady, two-carton-a-week smoker until George demands that he quit. While trying to get Leo to stop, however, George picks up the habit again, after a 15-year hiatus. Even George's doctor can't convince him to give up. Finally, armed only with their willpower and crossword puzzles, George and Leo decide to hole up and go cold turkey.
George hosts a tour of his home in period costume in hopes of becoming President of the Historic Conservancy, but his high hopes of finally winning the annual historic house tour end in a drunken haze after Leo and Ambrose spike the egg-nog.
George goes to war when a bookstore chain sets up shop on the island, offering 10,000 titles, CD-listening booths and cappuccino, and the owner vows to put George out of business. When Pendragon's, the flashy new bookstore with cappuccino and CDs, opens on Martha's Vineyard, George isn't worried about the competition. That's until Pendragon's manager May informs him that she's planning to run him out of town, which forces him to activate his secret weapon — Leo, and all his boyish charm.
Leo has a mild heart attack and, thinking he's going to that big Las Vegas Hilton in the sky, gathers his nine ex-wives together to atone for being such a bad husband. The wives, thinking that Leo is leaving them money, descend on the Vineyard, and on George.
In his efforts to become a better father and grandfather, Leo signs up for a business course. George is very supportive, and when he meets Leo's teacher, a woman who can make even mutual funds sound sexy, he's smitten. Unfortunately, the romance runs aground when Leo tries to use George's influence to pass a test.
Every week, George loses himself in a poker game with friends. But when Leo finds out that Walt, his supposed best friend, is also part of these weekly sessions, Leo is bitten by the jealousy bug and demands to be included. Meanwhile, Ted agrees to be hypnotized by Ambrose in order to deal with his squeamishness about the delivery room.
While he is reminiscing about Casey's childhood on the eve of her baby shower, Leo remembers that he convinced his old friend Robert Goulet to sing her a song on her seventh birthday. Eager to make a big splash at the shower, Leo tries to get Goulet, who is making a guest appearance at George's bookstore, to sing for Casey again. Unfortunately, this time, the song produces more than just applause.
Ted and Casey hire a nanny to care for their new baby, Alice, who seems to be the perfect person to care for the new baby. She's a registered pediatric nurse, warm, smart and loving. The problem is she's a little too loving when it comes to Ted. When Alice, mortified by her crush, decides to quit, it's up to George to figure out a way to keep her on the island and away from Ted.
Leo talks George into visiting his new love Tasha, a massage therapist, but Leo fumes when he's convinced that their session turned out to be more than professional. (Part one of two)
When the day comes for Leo and Tasha to get married, Tasha has a little trouble with the her memory. As she is saying her vows, Tasha accidentally pledges her troth to George instead of Leo, convincing Leo that she really does have feelings for George. Tasha has to agree, especially when she channels a past life in which she and George were an Egyptian princess and a pharaoh. Now, if they can just divorce in a past life... Meanwhile, Leo invites some of his former mob friends to a bachelor party, and one of the ""made men"" gets a crush on Alice. (Part two of two)
When George begins his new job teaching a business class at the local college, he discovers that his housekeeper, Margie, is one of his students. Then, George's new boss, Dean Shirley Martin, jumps to the conclusion that George and Margie are having an affair and fires him the first day for sexual harassment. George is mortified when Leo, Casey and Ted throw him a surprise party to celebrate his new career. Meanwhile, Alice tries to find a roommate and ends up with a male underwear model.