Based on Toby Young’s memoir of the same name, How to Lose Friends & Alienate People tracks the outrageous escapades of Sidney Young, a smalltime, bumbling, British celebrity journalist is hired by an upscale magazine in New York City. In spectacular fashion Sidney enters high society and burns bridges with bosses, peers and superstars.

After disrupting one black-tie event by allowing a wild pig to run rampant, Sidney catches the attention of Clayton Harding, editor of Sharps magazine, and accepts a job with the magazine in New York City. Clayton warns Sidney that he’d better impress and charm everyone he can, if he wants to succeed. Instead, Sidney instantly insults and annoys fellow writer Alison Olsen. He dares to target the star clients of power publicist Eleanor Johnson. He upsets his direct boss Lawrence Maddox and tries to make amends by hiring a stripper 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, sexy starlet develops an odd affection for him, and in time, Alison’s friendship might be the only thing saving Sidney from torpedoing his career.