Sideways

Jack is getting married soon. To enjoy the last remnants of his "freedom", Jack travels with his friend Miles on a sightseeing tour to California's wine country. Miles, a teacher and less successful author, wants to introduce his friend to his love of wine - he, in turn, just wants to have some more fun. In a small town where they stop off, Jack organises a double date with waitresses Stephanie and Maya. While Miles knows Maya from before and prefers to talk about wine, single mum Stephanie immediately falls in love with Jack, which presents him with a difficult decision and leads to various difficulties and complications...