Miles (Paul Giamatti) and Jack (Thomas Haden Church) are old friends. Seeing Jack about to get married, Miles laments his failed life: failed marriage, unattainable dream of becoming a writer, boring job, no longer young. Miles has a deep understanding of wine, so the two decided to go to the wine production base in California for a party. Of course, it would be best if they had a one-night stand. Sure enough, the two met the waitress and her Asian friend in California, where the wine is rich. Miles and Jack's affair made both of them excited. However, what happened next was a big disappointment. Their party plan was full of obstacles.