How to Lose Friends and Alienate People follows the escapades of Sidney Young (Pegg), a small-time aspiring British celebrity journalist who is hired by an upscale magazine after catching the attention of Clayton Harding (Bridges) during an event by creating a ridiculous scene with the help of a wild pig. Turning in a new direction, Sidney begins his descent into success and re-establishes himself from lonely outsider to confidante of starlet Sophie Maes (Fox), and enters into a love affair with colleague Alison Olsen (Dunst) that will either make him or break him.