Unemployed and unattached, Tom Chadwick is surprised when he's bequeathed an old chest of curios by his great-aunt Victoria, although he and his sister Bea can't remember ever meeting her. He finds an old black-and-white photo in the chest that his father, Keith, believes is Tom's great-grandfather, Harry. With the help of Mr. Pfister, his avuncular neighbor, and Pete, an old school friend, Tom tracks down Neville St. Aubrey, a strange expert in the field of antique photos, who discovers intriguing and revealing information about Tom's ancestor. Meanwhile, Pete tries to get Tom's love life back on track by setting him up with a “model pretty” date. He's just not sure what kind of model.

When Mr. Pfister discovers an unforeseen aspect of Tom's great-grandfather Harry's life, it leads Tom and Pete to the south coast of England, where Harry died many years before. They meet Sybil, an impossibly old woman who still lives next door to the house Harry lived in and remembers him from her childhood. Their investigation takes them to a regional theatre, where he and Pete learn more than they ever wanted to know about Harry's life and loves from Rex and Mitch, the two friendly gentlemen who run the theatre. It also inspires Tom and Pete to engage in a unique competition, but not before Pete has set Tom up on another extraordinary date.

Bea and Monk audition to perform at a children's birthday, while Tom starts digging deeper into the life of his grandfather William, who he suspects might have competed in the 1948 London "Austerity Games", a far cry from those of 2012. After learning more about the games from Mr. Pfister, Tom visits his great-aunt Victoria's friend Mildred, who is able to shed some light on William's former athletic prowess, and on why Victoria left Tom the chest of family curios. With Keith's help, Tom and Pete visit the gym where Tom's grandfather William trained for the Games, and meet some old-timers who actually knew him. While at the gym, Pete bravely accepts a challenge from a much younger timer. Bea and Monk perform their first professional gig at a wedding reception.

Tom finally has an interview for a job. He also discovers he has cousins in both Derbyshire and California, and makes a plan to visit and learn more about the Derbyshire branch of the family tree. Meanwhile, Pete has to perform a delicate "procedure" on an alpaca at the zoo. Tom, Bea, Keith, Luba and Monk drive up to the Derbyshire farm owned by their cousins from the North. Tom is interested to find out if the grass is really greener in the country, and equally determined to get to the bottom of a dark family secret. Culture clashes notwithstanding, Tom gets his answers and some family truths are finally revealed. The family-tree plot thickens as he also hears from his American cousin, Al, on the trip. Pete's life-affirming mission at the zoo proves to be a no less sticky venture.

Tom goes to the U.S. to visit his cousins, Al and Kitty Chadwick, in Los Angeles, to find out why his great-great-grandfather Charles left America for England more than a century ago, and he also gets to meet some other relatives at a family barbecue.

Tom's cousin Rick, an American Civil War enthusiast, helps Tom find out more about his great-great-grandfather Charles' mysterious activities as a soldier in the war.

Tom rents a classic convertible car and meets Ally for lunch, where they get to know each other a little better. Bea and Pete arrive to share Tom's last two weeks in America.

On their last day in California, Bea, Monk and Pete hit the beach, while Tom, accompanied by Ally, meets Toms distant cousin Melvin Schmelff, whose grandfather was Tumbleweed Tim, a famous silent-movie cowboy star.