In New York, Alex Hitchen is a kind of sentimental advisor, teaching each client how to date the woman of his dream. His present case is helping the clumsy Albert to date the wealthy and powerful Allegra Cole. Meanwhile, Hitch has a crush on the gossip columnist Sara, who was assigned to write about Allegra. When the best girlfriend of Sara has a love disillusion with a man that Sara thinks that is a client of Hitch, she plots a revenge against Hitch and the misunderstanding leads the two couples to a conflictive situation.

The true story of the kids who created modern skateboard culture is recreated in this drama. In the early '70s, skateboards were seen as a fad of the 1960s that had all but died out, but in a rough-and-tumble Venice, CA community known as "Dogtown," that was about to change. Tony Alva (Victor Rasuk), Stacy Peralta (John Robinson), and Jay Adams (Emile Hirsch) were three guys who liked to surf the rugged beaches around Venice and hung out at the Zephyr Surf Shop, a store run by Skip Engblom (Heath Ledger) that stocked gear for adventurous surfers and skateboarders. With the advent of new urethane wheels that connected with concrete in a way old metal and rubber wheels could not, Tony, Stacy, and Jay began exploring ways to translate radical surf style to skateboarding, and the guys invented a new way to skate inside the smooth, round surfaces of empty pools, employing vertical moves and edge flips that added a new and dramatic spin to skating. It didn't take long for word to spread about the wild new style of the Z-Boys, and they quickly became local celebrities, and later nationwide skating stars, though sudden fame took its toll on these young men. The true story of Lords of Dogtown was previously the basis of the acclaimed documentary Dogtown and Z-Boys, directed by former Z-Boy Stacy Peralta, who like Tony Alva served as a consultant on this project