Sideways (2005), by Alexander Payne, is the one about the atypical road trip taken by the wine expert/aspiring novelist, Miles (Paul Giametti), and his horndog friend Jack (Thomas Haden Church).

An absorbing comedy-drama, piercing and droll, it points up the theme of when the development of liaisons with other people is not matched by moral development, the manifestation of character.  These liaisons, these love affairs, are strongly desired, but are guardedly or hastily formed by men who are boys, i.e. Miles and Jack.  A boy, even so, can see himself as a loser, as Miles does, and so we sympathize.