Masquerade is a American romantic mystery thriller film directed by Bob Swaim and starring Rob LoweMeg TillyKim Cattrall and Doug Savant. Written by Dick Wolfthe film is about a recently orphaned millionairess who falls in love with a young yacht racing captain who isn't completely truthful with her about his past. Set in the upscale town of SouthamptonLong Island, young yachting captain Tim Whalen is having an affair with Brooke, who is married to Granger Morrison, Tim's boss. Tim is the new captain of Granger's racing sailboat Obsession. She meets Tim at a party, and agrees to go sailing with him. Olivia's alcoholic stepfather, Tony Gateworth, and his new live-in girlfriend, Anne Briscoe, reside in Olivia's house. Olivia is unable to evict him because her mother's will provided him access to the family's eight properties and grants him a one million dollar a year allowance, which barely covers his gambling debts. Olivia despises her stepfather, who married her mother for money. Olivia and Tim go sailing on Olivia's late father's sail boat, Masquerade. Later, at Olivia's mansion, a drunken Gateworth insults Tim, his former sailing competitor. Olivia and Tim begin dating and eventually fall in love. However, Olivia's newfound happiness is soon offset by another ugly confrontation with Gateworth who, claiming to be acting as her "guardian," wants Tim out of her life. Olivia confides to her aunt that Tim is the first man she has felt comfortable with and that he is uninterested in her money. Gateworth and Tim are actually conspiring to murder Olivia for her money. When Tim hesitates, Gateworth threatens to expose his shady past. He says the next step is for Tim to gain Olivia's confidence by protecting her. That weekend, Olivia and Tim sleep together. A drunken Gateworth barges into Olivia's bedroom as planned, but Tim double-crosses him and kills Gateworth with his own gun. Believing the police will accuse Tim of murder, Olivia claims she killed Gateworth in self-defense. Tim establishes an alibi with an unsuspecting Brooke. During the investigation, Officer Mike McGill — a childhood friend with a romantic interest in Olivia — finds evidence that Tim may have been involved in the killing but does not report it, presumably because of his feelings for Olivia. Anne begins questioning the investigation's findings, and tells the authorities about Olivia and Tim. Meanwhile, Tim ends his relationship with Brooke, who later confirms Tim's alibi to the police. Not long after, Anne informs McGill that her friend saw Gateworth at a diner with Tim; she is found hanged in an apparent suicide. McGill requests an autopsy. While sailing aboard MasqueradeOlivia proposes to Tim, but he is reluctant, saying he was previously convicted for writing bad checks. He also admits his affair with Brooke. His "honesty" impresses Olivia, and the couple marry. Olivia becomes pregnant soon after. That night, Tim drives to the marina where Meg Tilly Sex Scene secretly meets McGill, who in fact has planned everything. Tim is reluctant about murdering Olivia, but McGill insists she die in a staged accident. He threatens to put Tim away for Gateworth's murder if he fails to cooperate. When McGill learns Tim will not kill Olivia and they are sailing to Florida on Masquerade the next day, he sabotages the sailboat and plants incriminating evidence in Tim's dresser drawer. Tim discovers McGill's treachery and races to the marina to save Olivia, but the gas explosion kills him. In the marina office immediately after, Meg Tilly Sex Scene discovers a newspaper clipping with a photo of Tim, Gateworth and McGill, just as McGill enters the office.
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