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Sipherd reportedly told a jury in Los Angles on October 31 that the first time Weinstein assaulted her, she was 24 years old and attending TIFF as an aspiring actress and the second time, she was a 41-year-old woman looking to confront her abuser.
Weinstein has not been charged with the alleged assault, Sipherd detailed in her testimony
Sipherd and three other women are testifying against Weinstein, who is already serving 23 years, so prosecutors can prove he has a penchant for sexual assault, according to CP24.
Weinstein is facing 11 counts of rape and sexual assault against five women and is retaining that he did not have nonconsensual sex in his second criminal trial, as reported by The New York Times .
In 1991, Sipherd said she met Weinstein at a party during TIFF, and while she didn't know who he was, her friends recognized him as someone of importance in the industry.
"We got along very well," said Sipherd. "He was very intelligent. We had a wonderful conversation."
The news outlet reports that Sipherd said she found him charming as they spoke about books and films.
The first assault
The pair then went back to Weinstein's hotel room at the Four Seasons after they had left the party for a glass of wine at a café, where he told her he had a script in his hotel room that would suit her, according to Sipherd.
Once they got to his hotel room, Sipherd said, "It all happened very, very very quickly."
Sipherd said that Weinstein appeared out of the hotel bathroom holding a hot washcloth with his shirt unbuttoned and pulled her skirt off, according to CP24.
She claims Weinstein placed the cloth on her before saying, "my wife loves this," and held her down while he assaulted her with his hands and mouth and then started to rape her.
Sipherd reportedly told the jury she was "nauseous, scared, [and] terrified" and that she asked him what he was doing and repeatedly told him to stop.
She said she was able to get away during the assault and escape the room, but for weeks after, she claims Weinstein called her home, and after hanging up on his calls, she answered.
During their conversation, she says Weinstein convinced her to come to New York to meet a casting person who worked for him, and she decided to go with a friend who she planned to stick with her the entire trip, per CP24.
Weinstein's attorney Alan Jackson questioned Sipherd as to why she would take Weinstein's calls after the interaction she described and that he seemed like someone you'd cross the street to avoid.
"But you didn't walk the other way, or cross the street, or spit on him, you actually took his phone calls," said Jackson.
"Your rapist was persuasive in trying to get you to come with him to see him in New York?"
CP24 reports that Sipherd responded, "Yes."
Sipherd said she went to New York but didn't see Weinstein after he called her hotel room and asked to see her without her friend present.
The second assault
Seventeen years later, in 2008, Sipherd said she was living at the Four Seasons Hotel with her family when she ran into Weinstein in the hotel lobby during TIFF.
Sipherd said her blood "kind of stopped" and that she was "very angry."
Weinstein's assistant later came to her room asking to arrange a meeting between them, according to Sipherd.
"I wanted to confront him," said Sipherd, per CP24. "I felt like I was ready to give it to him."
Sipherd said she agreed to the meeting him and went to Weinstein's room, where she asked him, "How does it feel to be in front of the one woman who said no to you?"
She claimed he asked his assistant to leave the room and led her to her door, which she realized was a bathroom once Weinstein was blocking the path out.
According to CP24, Sipherd said Weinstein sexually assaulted her for the second time, groping her breasts and masturbating in front of her.
She said after the assault, he let her leave.
Jackson questioned why she went into the bathroom with Weinstein and described him escorting her in as "polite."
Sipherd said she didn't know the room was a bathroom because it was dark.
CP24 reports that Jackson went on to question why she didn't try harder to leave the situation or alert someone.
"You find yourself for the second time alone with this rapist and you didn't scream?"
Sipherd said she was "mortified" and "in shock" and that she didn't come forward about what had happened to her because of "sheer embarrassment."
If you or someone you know has been the victim of sexual assault, call the Assaulted Women's Helpline at 1-866-863-0511. You can also contact support services for male survivors of sexual assault at 1-866-887-0015. If you need immediate assistance, please call 911 or go to your nearest hospital. Support is available.