Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.
Marisa Ventura is a struggling single mom who works at a posh Manhattan hotel and dreams of a better life for her and her young son. One fateful day, hotel guest and senatorial candidate Christopher Marshall meets Marisa and mistakes her for a wealthy socialite. After an enchanting evening together, the two fall madly in love. But when Marisa's true identity is revealed, issues of class and social status threaten to separate them. Can two people from very different worlds overcome their differences and live happily ever after?
Gus Van Sant tells the story of a young African American man named Jamal who confronts his talents while living on the streets of the Bronx. He accidentally runs into an old writer named Forrester who discovers his passion for writing. With help from his new mentor Jamal receives a scholarship to a private school.