The movie trailer for How to Lose Friends and Alienate People made an early appearance on the Internet. The film is based on the memoir of journalist Toby Young and premieres in theaters on October 3, 2008.

British journalist Sydney Young lives in a run down flat above the Kebab Palace, but has always dreamed of living a glamorous life full of celebrities. He is hired by the prestigious Sharps magazine and moves to New York City. Once he arrives, Alison Olsen (Kirsten Dunst) is asked to show him around. The trailer reveals that Young is "out of line" during an interview, when he asks the actor, "that hamster thing you do, is that gay?" and he is "out of touch" when he proceeds to inquire if the actor is gay. On "take your daughter to work day," he is caught photographing a stripper when the children arrive. Young inadvertently sets off alarms in the building, spits food on the back of a woman, harms a dog in his care and ends up alienating everyone.