How to Lose Friends & Alienate People is a 2008 British comedy film based upon Toby Young's 2001 memoir How to Lose Friends & Alienate People. The film follows a similar storyline, about his five-year struggle to make it in the United States after employment at Sharps Magazine. The names of the magazine and people Young came into contact with during the time were changed for the film adaptation. The film version (adapted by Peter Straughan) is a highly fictionalized account, and differs greatly from the work upon which it was built.

Plot

Sidney Young, an aspiring British journalist who runs a failing polemical magazine, attempts to infiltrate a party organized by Clayton Harding (Jeff Bridges), the CEO of Sharps, one of the most prestigious magazines in the world. In doing so, he momentarily gains Clayton's sympathy, as the latter began his own career through polemics. Sidney is offered a job at Sharps, and moves to New York City, but he quickly earns the scorn of his colleagues, including Alison Olsen (Kirsten Dunst) and the manager Lawrence Maddox (Danny Huston), as a result of his rudeness, vulgarity, and general unattractiveness. He discovers that interviews with famous performers must be arranged by an influential publicist named Eleanor Johnson (Gillian Anderson), who imposes restrictions on published content, which offends Sidney, since he enjoys writing polemics. On one occasion, Sidney accidentally kills the dog of a rising actress named Sophie Maes (Megan Fox), to whom Sidney is intensely sexually attracted. To his fortune, Alison, who despises Sidney, agrees to help him conceal the mistake. Sidney gains Alison’s respect by explaining his disapproval of Eleanor's practices, and Alison reveals that she also despises her job, and has been working sporadically on a novel for years, which she hopes to publish. At a bar Sidney meets a girl (Charlotte Devaney) and brings her home. But she turns out to be transgender.