Masquerade (1988) Timeline Explained – Every Event in Order

• fuboTV Stream · HD
• MGM Plus Stream · HD
• MGM Plus Roku Premium Channel Stream · HD
• MGM+ Amazon Channel Stream · HD
• Philo Stream · HD
• Tubi TV Free with ads · SD
• Amazon Video Rent $3.99 · SD
• Apple TV Store Rent $3.99 · HD
• Fandango At Home Rent $3.99 · HD

Streaming availability powered by

1. 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.

   When

   early in Tim's tenure as captain

   Where

   Southampton, aboard Obsession

2. 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.

   When

   shortly after Olivia's return

   Where

   Southampton

3. 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.

   When

   following the initial meeting

   Where

   Masquerade, Southampton

4. 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.

   When

   that evening

   Where

   Olivia's mansion, Southampton

5. 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.

   When

   in the weeks following the mansion confrontation

   Where

   Southampton, various locations

6. 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.

   When

   that weekend

   Where

   Olivia's mansion, bedroom

7. 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.

   When

   during the early stages of the inquiry

   Where

   Southampton, police investigation

8. 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.

   When

   days after Gateworth's death

   Where

   Olivia's town; diner scene; police

9. 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.

   When

   shortly after Anne's death

   Where

   Police investigation office

10. 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.

    When

    during the Masquerade voyage

    Where

    Masquerade

11. 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.

    When

    not long after the engagement

    Where

    Olivia's mansion; wedding setting

12. 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.

    When

    that night

    Where

    Marina

13. 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.

    When

    the next day following the planning

    Where

    Marina; Masquerade drivetrain areas

14. 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.

    When

    immediately after the explosion

    Where

    Marina office

15. 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.

    When

    after Tim's death

    Where

    Funeral service