How to Lose Friends & Alienate People 2008

Sidney Young is an ambitious British journalist struggling to keep his polemical magazine afloat. In a bold move, he attempts to infiltrate a lavish party hosted by Clayton Harding, the CEO of Sharps, one of the world’s most prestigious magazines. Surprisingly, Sidney manages to gain Clayton’s attention, as the latter empathizes with Sidney’s beginnings in polemics.

This unexpected encounter lands Sidney a job at Sharps, prompting him to relocate to New York City. However, his introverted nature quickly earns him the disdain of his colleagues, including Alison Olsen and manager Lawrence Maddox. Sidney’s rudeness and vulgarity don’t win him many friends, pushing him further into isolation as he grapples with the demands of his new role where publicist Eleanor Johnson sets strict guidelines on what can be published.

In a turn of events, Sidney accidentally causes the death of a dog owned by rising actress Sophie Maes, who he finds irresistibly attractive. Although she despises him, Alison opts to help Sidney keep the incident under wraps. As they bond, Sidney earns Alison’s respect by voicing his disdain for Eleanor’s restrictive rules. During their conversations, Alison reveals her own struggles with the job and her long-standing dream of publishing a novel.

One night at a bar, Sidney strikes up a conversation with a girl, only to find out she is transgender. Humorous chaos ensues when Sidney later drags her to work to perform for Lawrence to obtain scandalous photographs.

During a party, Sidney uncovers a secret: Alison had been involved with Lawrence, although she has chosen to end the affair. As night turns into day, Sophie approaches a drunken Sidney but he opts instead to play caretaker for the uninhibited Alison, who also needs a ride home. At Sidney’s apartment, he introduces Alison to his distinguished father, a renowned philosophy professor with aristocratic connections.

In a stroke of bad luck, Sidney attempts to ask Alison out, only to learn of her rekindled relationship with Lawrence, who just finalized his divorce. Facing overwhelming despair, Sidney compromises his integrity and pleads to work with Eleanor, who surprisingly agrees. Meanwhile, Clayton decides to create a shakeup at the magazine, leading to the ousting of Lawrence and Alison, and paving the way for Sidney’s rapid rise within the company.

As he becomes more entrenched in the world of celebrity and prestige, Sidney loses sight of his earlier ideals, cultivating a reputation as a writer who caters to the whims of others to get ahead. The night before the ambitious film-awards ceremony, Sidney finds himself at another party hosted by Sophie, where he is coerced into giving up a cherished gold ring, a keepsake from his late mother.

Ultimately, the allure of high society disgusts him once more. At the ceremony, just as Sophie approaches the stage to accept her award, Sidney takes a stand: he confronts her and confesses to killing her dog while reclaiming the ring. This dramatic outburst garners unwanted media attention, leading to chaos. However, Sidney is determined to return to Alison in New York City, where they finally embark on a relationship after her separation from Lawrence.