July 19, 2015 10:08 AM EDT

A deposition uncovered Saturday shines new light on Bill Cosby’s extramarital relationships and the accusations of sexual assault from many women.

The court documents, first published by the New York Times Saturday, come from 2005 and 2006 depositions related to accusations of molestation from Andrea Constand.

In the questioning, Cosby denies allegations of assault, but admits to the dogged pursuit of extramarital relations, often in an ethically dubious, if still legal, fashion. Here are four things we learned:

Cosby obtained seven Quaaludes prescriptions

The deposition provides new details about how Cosby obtained the drug Quaaludes, which functions as a sedative. Cosby said in the deposition that he told a Los Angeles doctor that he wanted the drug for back pain, but he assumed the doctor knew that he actually wanted to use it for other purposes. “Quaaludes happen to be the drug that kids, young people were using to party with and there were times when I wanted to have them just in case,” Cosby said.

Asked how he used Cosby used them, the comedian said he never took one himself and instead offered them “the same as a person would say have a drink.”

Cosby made light of the accusations

Even in a deposition where Cosby theoretically had something to lose, the comedian couldn’t help but make light of the situation. In one moment, Constand’s lawyer told Cosby, “I think you’re making light of a very serious situation.” Cosby agreed: “That may very well be.”

Cosby used personal details to lure women

Cosby admitted to discussing personal details of women’s lives in hopes they would sleep with him. In one case, he discussed the cancer treatment of a woman’s father. Asked if he asked “her those questions because [he] wanted to have sexual contact with her,” Cosby replied, “Yes.”

Cosby put a lot of effort into hiding his affairs from his wife

Cosby provided women with financial assistance in hopes of wining their silence. Doing that often involved a number of tactics to keep his wife from becoming suspicious. In at least one case, Cosby had his agency, the William Morris Agency, cut a check to a woman he allegedly drugged. Cosby then reimbursed the agency. Asked who he hoped to prevent from knowing about the payment, Cosby replied, “Mrs. Cosby.”

Write to Justin Worland at justin.worland@time.com.

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