Olly Pickering and Murray are childhood friends who drift apart when Olly heads to university. In this new chapter of his life, Olly meets James in London, and a ridiculous moment—Murray vomiting all over James—sparks instant enmity between them that echoes through the days to come.
Olly makes a splash in the literary world when he writes the first two chapters of a novel and an editor pays him a hefty sum of $50,000 to finish it. But success is short-lived; Olly is struck by writer’s block and quickly loses the money he had earned. He finds work in London as an assistant to Dana, a busy editor who specializes in self-help books for women, a job that becomes a new foundation for his life amid the chaotic pace of the city.
Across town, James is preparing to marry in London and throws a party to celebrate. Olly arrives late and endures a humiliating moment when he’s covered in pigeon droppings in Trafalgar Square. In an impulsive twist, he changes into some women’s trousers, a choice that sets the tone for the party’s unpredictable night. James asks Olly to be his best man and to deliver a funny speech, a request that makes Olly feel both flattered and out of place.
At the party, Olly’s awkwardness is amplified when he’s admonished by Becka, the rightful owner of the trousers he borrowed, and he crosses paths with Sarah, who turns out to be James’s girlfriend, though Olly doesn’t realize it at first. On a balcony with a view over the city, Olly is struck by Sarah’s presence, while James develops the impression that Olly is falling for Becka. The night becomes a tangled web of misinterpretations, with friends like Harry, Tania, and the barrister Graham weighing in from a pub, and Murray quietly plotting to derail the wedding.
Murray takes steps to manipulate the couple’s fate. He phones Sarah on Olly’s behalf to arrange a film date and poses as a reminder of James’s supposed womanizing ways. He also engineers scenes to test James’s fidelity, arranges Olly’s meeting with Sarah at a department store wedding registry, and even phones James from a porn shop while appearing at Becka and Sarah’s flat with rumors that James wants to sell it.
Back at Selfridges, Olly is surprised to see Dana attempting on a wedding dress during a workday, a moment that foreshadows the chaos in Olly’s professional life. Dana fires Olly the next day, an action that Graham tries to reverse by convincing her to rehire him; the attempt ends in a personal victory for Graham but not a job, though it leads to a date. Sarah later uncovers red knickers Murray had hidden to frame James and discovers a porn shop number in James’s phone, prompting her to call off the wedding.
Murray throws a surprise party for Olly—one guest missing being James—and then confesses that the entire set of schemes was his idea. Olly writes a letter to Sarah on James’s behalf, and James pretends to be heartbroken enough to leave for New York. Sarah is swayed by the ruse and agrees to marry James, leaving Olly to wrestle with what he believes is the right outcome. Murray later reveals that James has been unfaithful, though Olly struggles to accept the accusation as truth.
The stag party for James turns wild, featuring two strippers dressed as policewomen, and James finally confesses the betrayal: he has slept with someone else because Sarah does not fully satisfy him, though he still wants to marry her for the family’s money and connections. Olly wants to expose the truth, but James quickly handcuffs him to a pillar, keeping the secret for the moment.
Freeing himself, Olly races to the wedding venue to stop the ceremony, aided by Becka, who reveals that James has indeed been unfaithful with his secretary and blames another woman. In a wrenching turn, Sarah chooses to call off the wedding.
Months later, Becca and Murray marry, and Olly and Sarah finally come together. Olly returns to his craft, picking up the pen with renewed energy and producing a bestseller that signals a new chapter for him—and a quieter, more hopeful end to the tangled story. In the end, the film traces how friendship, ambition, and love collide in a city that never stops changing, leaving Olly with a sense of closure and a new path forward.
