Weinstein is charged with raping the woman in a New York City hotel in March 2013 and performing a forcible sex act on another woman, Mimi Haleyi, in 2006.
The witness acknowledged under cross-examination that after the alleged 2013 attack she had breakfast with Weinstein and two of her friends that morning, then went to a meeting with one of his staffers and ended the day by meeting him at a movie premiere.
The next day, she met with Weinstein and his daughter in another hotel lobby on his birthday, according to her testimony.
Last week, under direct examination, the woman testified that she had engaged in consensual sexual relationship with Weinstein both before and after the March 2013 alleged attack -- as well as a subsequent attack she detailed nine months later at the Peninsula Hotel in Los Angeles, for which Weinstein is not charged.
In that incident, she testified that Weinstein violently raped her after she told him she was dating an actor, demanding the sex by telling her beforehand "you owe me one more time" and afterward telling her, "Now you can go and have your relationship and what you can do is bring me other girls."
Weinstein is charged with a total of five felony counts. He has pleaded not guilty to all charges and denied ever engaging in nonconsensual sex.
During a daylong cross-examination, defense attorney Donna Rotunno zeroed in on the witness' previous testimony that she was never romantically or sexually interested in Weinstein -- who was more than twice her age when he allegedly raped her.
"Every time you reached out to Mr. Weinstein and made it sound like you wanted to see him, you were acting?" Rotunno asked.
"I wanted him to believe I wasn't a threat," the witness replied.
At times the witness' responses to direct questions were vague or inchoate.
Noting that the witness only got one substantial audition -- in 2013 -- from her connection to Weinstein, Rotunno asked, "So you stuck around for the rest of 2013 [and through] 2016, because you thought he was grotesque and you didn't want to have sexual relations with him?"
"I engaged with my abuser because of what I believed in my mind and the perception of the society I lived in and the things and the ways he did threaten me, and it was always in my best interest to feel that the temperature gauges between us, I wanted to know that we were okay and something was not going to happen to me," she responded.
At another point, Rotunno asked her, "You manipulated Mr. Weinstein every single time, isn't that correct?"
"I felt there was an aspect to the way I felt I needed to protect myself that had an element of manipulation," the witness responded.
At another point, the witness explained that "to understand what I say, you have to understand my perspective and my beliefs and that's not something I've really been allowed to dive into." She testified last week that she was raised in what she described as a Christian "cult."
It wasn't until 4 p.m, as her fifth hour of cross-examination was beginning, that she finally got the chance to expand upon that part of her thinking.
Throughout her testimony, the witness described a complicated relationship with Weinstein in which she said initially consented to mutual oral sex because she felt sorry for him, but ultimately felt degraded and abused and ultimately ended the relationship in 2016.
She testified on Monday that "oftentimes before we engaged in something sexual, there was a negotiation. … The more I realized I was feeling like I was just being used, I tried not to have sexual encounters with him and we'd get into this back and forth … I wanted to reduce what he wanted from me."
At another point during Rotunno's cross-examination, the witness acknowledged that she arranged with Weinstein to meet her mother.
"This is after you claim Mr. Weinstein raped you in New York, and after [the incident at the] Peninsula?"
The witness acknowledged that it was, saying that her mother was badgering her to meet Weinstein, but had no idea of either their consensual sexual relationship or the witness' claim that Weinstein raped her.
"You made a choice to have sexual encounters with Harvey Weinstein when you weren't attracted to him," Rotunno charged at another point. "You liked going to parties, you liked the power and you liked the opportunities."
"That's your version," the witness replied.
In a dramatic May 2014 note to a boyfriend she had been dating during some of the time she said she was also with Weinstein, the witness explained to the boyfriend that, like Weinstein, her father had dated "women younger than me."
As part of her cross-examination, Rotunno asked the witness to read the note aloud to the court.
"Harvey validated me in ways my parents never did," she said, reading from the email. "My parents would never invest in me like that. …Harvey was my father's age and he gave me all the validation I needed."
She said she continued to engage in consensual sexual relations with Weinstein after she claims he raped her because she had been sexually assaulted in the past.
“I remembered the day I realized I was controlling my world because I was sexually assaulted, and that story played out where I played into sexual dynamics with people to feel like I would never be taken advantage of again."
She began to sob, and struggled without success to compose herself.
A break was called, and the judge ended her testimony for the day. It will resume Tuesday morning.