The Best Man

The Best Man

Year: 2005

Runtime: 96 mins

Language: English

Director: Stefan Schwartz

ComedyRomance

Olly Pickering’s writing career stalls under a bout of writer’s block, forcing him to crash at his friend Murray’s flat after losing his savings. When his college mate James asks Olly to be best man, Olly meets Sarah, whom he first assumes is the bride’s sister. Discovering she’s actually the bride, he hopes Murray—who isn’t fond of James—can help unite them.

Warning: spoilers below!

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Timeline – The Best Man (2005)

Trace every key event in The Best Man (2005) with our detailed, chronological timeline. Perfect for unpacking nonlinear stories, spotting hidden connections, and understanding how each scene builds toward the film’s climax. Whether you're revisiting or decoding for the first time, this timeline gives you the full picture.

1

Olly's windfall from early writing

Olly completes the first two chapters of a novel and an editor pays him $50,000 to finish it. Writer's block soon hits, and he loses all the money, leaving him broke. The setback forces him to rethink his career and seek steady work.

Early in his career Home
2

Olly moves to London to work for Dana

He moves to London and takes a job as assistant to Dana, an editor of self-help books for women. This new position puts him in the city’s publishing orbit and closer to the social circle he will later encounter. The money trouble from before drives him to accept steady work rather than ideal acclaim.

Shortly after the windfall London
3

James's London wedding and party invitation

James is planning a wedding in London and throws a party to celebrate. He invites Olly to be part of the festivities and to act as his best man. Olly attends, not realizing how tangled his feelings will become.

Before the wedding London
4

Pigeon droppings in Trafalgar Square and change of clothes

On the way to the party, Olly is stuck in Trafalgar Square and is covered in pigeon droppings. Embarrassed, he improvises and changes into a pair of women's trousers. The mishap sets a comic yet chaotic tone for the evening.

During travel to party Trafalgar Square, London
5

Love at the balcony: Olly meets Sarah

On the balcony at the party, Olly finds himself falling for Sarah. James, however, suspects Olly is attracted to Becka instead. The moment sparks a confusing love triangle that drives the rest of the plot.

During the party James's party, London
6

Pub debate about the situation and Murray's plan

In a pub discussion, Harry, Tania, and barrister Graham talk through the situation. Murray reveals that he intends to see the wedding canceled. The mood is tense as alliances shift and plans intensify.

Shortly after the party London pub
7

Murray's manipulation of Sarah and Olly's social life

Murray phones Sarah on Olly's behalf to set up a film date and sow doubt about the wedding. He also stages meetings for Olly with Sarah at Selfridges to shape the wedding list. From Stan’s porn shop, he even phones James, hinting that he should sell the flat.

Between the party and the wedding Selfridges; Stan's porn shop, London
8

Dana's wedding dress moment and Olly's firing

Back at Selfridges, Olly watches Dana try on a wedding dress, despite her supposed marriage and a meeting. The sight unsettles Olly and soon afterward Dana fires him. Graham tries to persuade Dana to hire him back, and instead ends up with a date.

The day after the party Selfridges, London
9

Sarah discovers red knickers and James's frame

Sarah discovers red knickers Murray had hidden to frame James and also finds a porn shop number on James's phone. The evidence convinces Sarah that James has been unfaithful. She immediately calls off the wedding.

After Dana's firing Sarah's home
10

Murray's surprise party for Olly

Murray throws a surprise party for Olly, inviting everyone except James. He finally admits to having plotted everything, and Olly writes a letter to Sarah on James's behalf. James pretends he is leaving for New York, a ruse that deepens the rift.

Sometime soon after London
11

James's alleged infidelity surfaces

Murray tells Olly that James has slept with someone else while dating Sarah. Olly chooses not to believe him, clinging to a fragile loyalty. The rumor further complicates the wedding plans.

Following the party London
12

Stag party confrontation

Olly attends James's stag party, which turns wild with two stripper policewomen. James admits he has been unfaithful and reveals he wants to marry for money and status. Olly contemplates exposing the truth but is restrained when James handcuffs him to a pillar.

Night before wedding James's stag party
13

Final intervention at the wedding venue

Olly reaches the wedding venue and with Becka's help counters James's deception. Becka exposes James's infidelity with his secretary. Sarah decides to call off the wedding.

Wedding day Wedding venue
14

Six months later: Becca, Murray, and a new life for Olly and Sarah

Six months later, Becka and Murray marry. Olly and Sarah end up together, and Olly returns to writing, producing a bestseller. The success seals the new chapter of their lives.

Six months later London

Last Updated: October 09, 2025 at 15:09

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