Eddie Miller (Robert Forster) has been selling jewelry to small stores in Pennsylvania for 30 years. After suffering a heart attack, he is told that he is no longer “insurable” to carry a line worth over a million dollars.  The only way Eddie can continue to work in the business he clings to for support is by breaking in his own replacement, Bobby Walker (Donnie Wahlberg), a brash kid whose every move rubs him the wrong way.

Other than a two week training course, Bobby’s only “road” experience has been filling vending machines with pretzels.  Outrageous profanity spills from his mouth at the worst possible moments.  He falls asleep in a store.  He shows more interest in romancing local waitresses than jewelers.

After several days of putting up with him, Eddie gets past Bobby’s arrogant exterior.  Bobby accepts Eddie as his mentor.  The two begin to form a tentative bond.  Endless days of driving the PA countryside begin to break down the decades that separate them.  Bobby admits to having cheated on the company’s “psychological” test.  Eddie talks about the wife he lost to a chronic illness.

As a way of expressing his gratitude, Bobby attempts the nearly impossible; to find a woman to fill the void in Eddie’s life.  When a couple of Bobby’s conquests show no interest in the older man, Bobby resorts to a little more unorthodox strategy; he introduces Eddie to Tina (Jasmine Guy), an old friend who runs a dowdy, backwoods massage parlor called “the Altoona riding club.”  But the sort of women Tina employs are not exactly what Eddie is used to.

After a comic disaster at the club the unexpected happens.  Eddie begins to loosen up.  Tina introduces him to Katie (Bess Armstrong), a woman he can relate to.  But the road is treacherous.  The diamonds they carry make Bobby and Eddie easy targets.  And as Eddie begins to take chances he becomes vulnerable to the sort of danger he has spent his whole life trying to avoid.