Masquerade

Masquerade

Year: 1988

Runtime: 91 mins

Language: English

Director: Bob Swaim

DramaRomanceThrillerThrillers and murder mysteriesSuspenseful crime thrillers

A recently orphaned heiress meets a young racing yacht captain on Long Island. He shows interest in her and, being heiress to $200,000,000, love may not be the reason.

Warning: spoilers below!

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Timeline – Masquerade (1988)

Trace every key event in Masquerade (1988) 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

Tim becomes captain of Obsession and begins an affair with Brooke

Tim Whalen takes the helm of Granger Morrison's racing sailboat Obsession. At the same time, he starts an affair with Brooke, Morrison's wife, setting a tense dynamic between employer and employee and hinting at trouble ahead.

early in Tim's tenure as captain Southampton, aboard Obsession
2

Olivia returns home and meets Tim at a party

Olivia Lawrence returns to Southampton after her mother's death and encounters Tim at a social gathering. They form a spark, and she agrees to go sailing with him, opening the door to a new romance.

shortly after Olivia's return Southampton
3

Tim and Olivia sail Masquerade and begin dating

Tim and Olivia take to Olivia's late father's sailboat Masquerade for a sail where their connection deepens. Their shared moments at sea lead to the start of a romance.

following the initial meeting Masquerade, Southampton
4

Gateworth provokes Tim; Olivia reveals Tim's sincerity

Back at Olivia's mansion, Gateworth insults Tim, fueling a volatile scene. Olivia privately tells her aunt that Tim is the first man she has trusted and that his interest isn't in her money.

that evening Olivia's mansion, Southampton
5

Conspiracy forms: Gateworth and Tim plan to murder Olivia

Gateworth and Tim secretly plot to murder Olivia for her wealth. Tim hesitates, but Gateworth threatens to expose Tim's past, pushing him toward a dangerous plan and involving him in a deadly ruse.

in the weeks following the mansion confrontation Southampton, various locations
6

Olivia and Tim sleep together; Gateworth is killed

That weekend, Olivia and Tim sleep together, solidifying their bond. Gateworth barges into Olivia's room as part of the plan, but Tim turns the tables and kills Gateworth with his own gun, leaving Olivia to cover it as self-defense.

that weekend Olivia's mansion, bedroom
7

The investigation begins; McGill suspects Tim

With Gateworth dead, an investigation starts. Officer Mike McGill, a friend with feelings for Olivia, finds indications that Tim may be involved but keeps quiet, torn between duty and his affections.

during the early stages of the inquiry Southampton, police investigation
8

Anne questions the findings; a new lead surfaces

Anne questions the investigation's findings and informs authorities about Olivia and Tim. She later tells McGill that a diner sighting might connect Gateworth to Tim. Anne is found hanged in an apparent suicide, prompting an autopsy request.

days after Gateworth's death Olivia's town; diner scene; police
9

Autopsy is requested amid growing suspicions

McGill requests an autopsy to resolve lingering questions about Gateworth's death and the broader conspiracy tying Tim and Olivia together. The move deepens Olivia's fear and complicates the case.

shortly after Anne's death Police investigation office
10

Olivia proposes to Tim during a Masquerade voyage

While sailing Masquerade, Olivia proposes to Tim, but he reveals a past conviction for bad checks and admits the affair with Brooke. Despite the shadows over him, Olivia's faith deepens and they become engaged.

during the Masquerade voyage Masquerade
11

The couple marries and Olivia becomes pregnant

Tim and Olivia marry, with Tim's honesty and awkwardness about his past shaping their union. Olivia becomes pregnant soon after, cementing a fragile happiness amid lingering danger.

not long after the engagement Olivia's mansion; wedding setting
12

McGill pressures Tim and plans a staged kill

That night, Tim visits the marina to meet McGill, who has orchestrated everything. Tim resists killing Olivia, but McGill threatens to imprison him for Gateworth's murder if he fails, pushing for a staged accident instead.

that night Marina
13

Sabotage and the fatal explosion on Masquerade

McGill sabotages Masquerade and plants incriminating evidence in Tim's drawer. Tim discovers the treachery and rushes to the marina to save Olivia, but a gas explosion seals his fate.

the next day following the planning Marina; Masquerade drivetrain areas
14

Olivia unravels the conspiracy and McGill dies

In the marina office, Olivia finds a newspaper clipping linking Tim, Gateworth, and McGill. McGill enters and attempts to kill her, but she pushes him out a window to his death, ending the conspiracy along with Tim's story.

immediately after the explosion Marina office
15

Tim's funeral and a final reveal

At Tim's funeral, Olivia's lawyer notes that Tim had recently asked to be removed from her will and that he ultimately came to love her. The case closes with Olivia bearing both loss and a complicated love that survived the storm.

after Tim's death Funeral service

Last Updated: October 09, 2025 at 14:35

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Masquerade Summary

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Masquerade Summary

Characters, Settings & Themes in Masquerade

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Characters, Settings & Themes in Masquerade

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