Miles is a troubled middle-aged man who teaches English for living. He's also an unsuccessful writer so far. He divorced 2 years ago before the events of the film. He seems to suffers from anxiety disorder and depression with a bit of mild alcoholism on the side due to his wineloving nature.Miles takes a road trip with his old freshman year college friend Jack before Jack gets married, who is quite the exact opposite to him. Miles is a negative guy , while Jack is a positive guy . Miles is passive, while Jack is active. Miles drinks a lot, while Jack wants sex a lot. Miles is intelligent, while Jack relies on instinct. Miles is a writer, while Jack is an actor. The list can go on. Even with their differences, they have a very good friendship with deep roots. This makes them best friends.Miles meets Maya, a waitress in a restaurant Miles goes in with Jack. Afterwards Jack meets Stephanie, who's a bartender and asks if she knew Maya. Stephanie knows Maya really well and they decide to have some fun in their free time (Miles, Jack, Maya and Stephanie). Jack falls for Stephanie while Miles falls for Maya, slowly but surely.Later Miles accidently tells Maya that Jack's getting married which results in Jack's broken nose, requiring a surgery or two. Maya does not approve of the lies which were made up to cover up Jack's wedding so Maya's and Miles' relationship goes on hold. Miles does tell Maya how he feels, before she leaves.After the trip, Miles meets his ex-wife and his new husband, in utter but supressed pain and goes home. We see miles drinking the 1961 Cheval Blanc in a fast food restaurant. Miles also gets back to teaching. In the end, Maya leaves a message in Miles' answering machine about his writing. She encourages him to keep doing so, even though the book was not published. After hearing this, Miles decides to go see Maya personally and knocks on her door. Show less «