Annie's Point (2005)

Richard Eason is flat-out filling his late father's shoes as CEO of an east Coast real estate developing company, so he can't spend nearly as much time with mother Annie and daughter Ella as they would like. Annie is dead-set on visiting a place in California where she and her late husband hoped to build their dream house and convinces Ella, who wants to drop out of school and aspires a singing career, to drive along. Ill-prepared but tempestuously stubborn, they embark on an adventurous road trip, where Ella meets hunky waiter Scott Tardy. Learning Annie needs surgery soon, Richard gives chase.