How to Lose Friends & Alienate People

Sidney Young, an ambitious journalist, struggles to maintain his polemical magazine while seeking recognition in the competitive media landscape. His bold decision to infiltrate a lavish party hosted by Clayton Harding, the CEO of Sharps, marks the beginning of his journey into high society.

Sidney captures Clayton's attention, putting his unique approach to journalism in the spotlight. This unexpected encounter results in Sidney landing a job at Sharps, compelling him to relocate to the bustling city of New York.

Upon joining Sharps, Sidney quickly realizes that his introverted demeanor does not endear him to his colleagues. His rudeness and vulgarity set him apart, leading to his isolation and conflicts with manager Lawrence Maddox and publicist Eleanor Johnson.

In a tragic turn of events, Sidney accidentally causes the death of a dog owned by the rising actress Sophie Maes. This incident becomes a source of tension, as despite her hatred for him, Alison Olsen decides to help him cover it up.

As Alison helps Sidney manage the fallout from the accident, they begin to bond over shared aspirations and frustrations. Sidney earns Alison's respect through candid discussions about Eleanor's strict editorial guidelines and her own ambitions to publish a novel.

Sidney's adventurous spirit leads him to strike up a conversation with a girl at a bar, only to discover she is transgender. The humorous encounter escalates when he later brings her to work, hoping to use her for scandalous photographs.

Sidney uncovers a revelation at a party: Alison was previously involved with Lawrence Maddox, but has chosen to end their affair. This newfound knowledge complicates Sidney's feelings as he grapples with his own attraction to Alison.

After a night of partying, Sophie approaches a drunken Sidney. However, he chooses to care for Alison, who needs a ride home, demonstrating his growing responsibility and concern for her well-being over fleeting pleasures.

Just when Sidney gathers the courage to ask Alison out, he learns of her rekindled romance with Lawrence, who has recently finalized his divorce. This shocking news leaves Sidney in despair as he contemplates his next steps.

Facing turmoil in his career, Sidney pleads with Eleanor to gain her cooperation, compromising his principles to advance within the company. Surprisingly, she agrees, setting the stage for a significant shift in Sidney's professional life.

Clayton Harding implements changes at Sharps, leading to the ousting of Lawrence and Alison. This shakeup opens doors for Sidney, marking his rapid ascent within the organization as he adjusts to the new dynamics.

As Sidney rises in the ranks, he becomes increasingly entrenched in the world of celebrity journalism. He loses touch with his earlier ideals, earning a reputation for pandering to the demands of others in his quest for success.

On the eve of the film awards ceremony, Sidney finds himself at another party thrown by Sophie. The event takes a turn when he is coerced into relinquishing a cherished gold ring, a memento from his late mother, showcasing the pressure of high society.

During the film awards ceremony, Sidney confronts Sophie on stage, confessing to accidentally killing her dog while reclaiming his mother's gold ring. The dramatic revelation causes chaos and draws unwanted media attention to him.

After the tumultuous events at the awards, Sidney resolves to return to New York, seeking reconciliation with Alison. Their relationship blossoms as she separates from Lawrence, allowing them to finally embark on their long-awaited romance.