"I have three friends for you to make you relax", Cosby said he told Constand, according to a deposition transcript re-read to the jury Monday night.
The fate of Bill Cosby lay in the hands of a USA jury who deliberated over dinner and into the night on whether or not the disgraced entertainer sexually assaulted a woman at his home more than 13 years ago.
The fast-moving case went to the jury of seven men and five women on day six of the trial after closing arguments gave differing portrayals of what happened between Cosby and Andrea Constand at his suburban Philadelphia estate.
Steele described Cosby as a calculating sexual predator who not only drugged and assaulted Constand more than a decade ago, but also cruelly recast the attack as consensual and romantic.
McMonagle said that while the comedian had been unfaithful to his wife, he did not commit a crime.
Prosecutors countered by saying "fancy lawyering" can't save Cosby from his own words - namely, his admission about groping Constand after giving her pills he knew could put her to sleep.
"Drugging somebody and putting them in a position where you can do what you want with them is not romantic", he added. "It's criminal", Montgomery County District Attorney Kevin Steele said.
Earlier in the day, Brian McMonagle, one of Cosby's lawyers, highlighted Constand's alleged inconsistencies and those of Kelly Johnson, another accuser who testified on Constand's behalf.
Instead Cosby's lawyer used a 90-minute closing statement to accuse Constand of hiding the true nature of their emotional relationship from the police and concocted the allegations to take advantage of the wealthy, older star. Cosby has pleaded not guilty to three charges of aggravated indecent assault.
The case has sparked debate over celebrity, race, power and gender. They complained that prosecutors were improperly striking blacks from the jury chosen in Pittsburgh.
The defence offered its closing argument after presenting a single witness: a detective who reminded jurors that police wondered why Constand had visited with Cosby at a casino.More news: 18 injured after Massachusetts ferry crash
The big-money mouthpiece said Constand, 44, a Toronto massage therapist, called Cosby dozens of times after the alleged assault. Constand said she had to return calls from the Temple University trustee because he was an important booster and she worked for the women's basketball team.
"This isn't talking to a trustee, this is talking to a lover", he said.
"Just tell the truth - what are we doing here?" he continued, one of many exclamations he made in a fiery and at times histrionic closing that lasted almost two hours. "And he danced and she deserved better", he said pointing to Camille, who had joined her husband in court for the first time this trial. She says they left her semi-conscious.
In his two-hour final pitch to jurors, McMonagle painted Constand as a liar who badly damaged her credibility with conflicting statements to police when she first came forward in 2005. He says he gives her drugs.
McMonagle defended the good faith of his client, saying Cosby had agreed to speak at length to investigators in 2005 when he could have kept silent, and rounded on the press. She testified the pills left her semi-conscious and unable to tell Cosby to stop. His deposition was sealed for years until a judge released parts in 2015 at the request of The Associated Press, prompting a new set of prosecutors to take a fresh look at the case.
In his argument, McMonagle emphasized that Cosby consistently portrayed the encounter as consensual. The implication is that she was after money from Cosby, one of America's wealthier stars. "We're talking about all the man's tomorrows", he said.
In his two-hour closing remarks to the jury, Steele made repeated reference to Cosby's 2005 and 2006 deposition testimony from a civil lawsuit filed by Constand, who was in the courtroom, as well as Cosby's January 2005 statement to Cheltenham and Montgomery County detectives.
"Andrea Constand's own words, just what she told you, should sustain a conviction in this case", Mr Steele said.
The defence case consisted of a six-minute appearance by a detective, seemingly created to remind jurors that Andrea Constand had visited with Cosby at an out-of-state casino and that police knew he had vision problems even then.
"There are some things in this case that should be fuzzy. Why?" That's unusual, said former prosecutor Dennis McAndrews.
He also said he gave Ms Constand three half-tablets of the cold and allergy medicine Benadryl before the "petting" began.