- Directors: Robert B Weide
- Producers: Stephen Woolley, Elizabeth Karlsen
- Writers: Peter Straughan, Toby Young
- Genres: Comedy, Romance
- Actors: Simon Pegg, Kirsten Dunst, Jeff Bridges, Megan Fox, Danny Huston, Gillian Anderson
How to Lose Friends & Alienate People tracks the escapade of Sidney Young (Simon Pegg), a smalltime, bumbling, aspiring British celebrity journalist who is hired by an upscale magazine in New York City. He tries to enter a party with a pig, pretending it is the pig of a sequel of the film Babe, but is refused. He locks it in his hotel room and goes to the afterparty, but when the room is serviced the pig escapes to the party where it runs rampant. Due to this incident Sidney catches the attention of Clayton Harding (Jeff Bridges), editor of Sharps magazine, and accepts a job with the magazine in New York City. Clayton warns Sidney that he’d better charm everyone he can, if he wants to succeed. Instead, Sidney instantly insults and annoys fellow writer Alison Olsen (Kirsten Dunst). He dares to target the star clients of power publicist Eleanor Johnson (Gillian Anderson). He upsets his direct boss Lawrence Maddox (Danny Huston), and tries to make amends by hiring a stripper (Charlotte Devaney) to dance for Lawrence during a staff meeting. Sidney, of course, doesn’t stop there, finding creative ways to annoy nearly everyone. His saving grace: a rising model Sophie Maes (Megan Fox) who develops an odd affection for him, and in time, Alison’s friendship might be the only thing saving Sidney from torpedoing his career.