But it wasn't until Friday (Saturday NZT) - on the fifth day of Cosby's trial - that jurors learned what was going through the comic legend's mind during those conversations.
"I'm apologizing because I'm thinking, 'This is a dirty old man with a young girl.' I said to the mother it was digital penetration".
Cosby didn't respond when The Associated Press asked if he'll take the stand in his own defence.
Prosecutors were limited to calling just two accusers to the stand: Constand and another woman who says Cosby assaulted her in similar fashion at a Los Angeles hotel bungalow in 1996.
Prosecutors have cited the 2015 ruling by a federal judge in Philadelphia to unseal excerpts of that deposition as an impetus in their decision to reopen the Constand investigation after a decade.
Assistant District Attorney Kristen Feden point out that the defense had questioned Constand's behavior, spending nearly an hour grilling her about phone calls to Cosby in the weeks after the alleged assault. Cosby said. "And I put these things in the mail and these people are in Canada. Most of us have this expectation most rapes are violent, involve strangers etc.", she said. Cosby and his lawyer wouldn't comment on that, and the defense has not disclosed its strategy or the witnesses it intends to call during its portion of the case. She also said a survivor might not remember every detail of an assault, like how long it lasted or the date, but can remember parts of it like "how someone's tongue felt in their mouth", for example.
During his testimony, Reape asked why Cosby would give pink Benadryl to authorities if he claimed to still have the blue pills.
"I don't think so", Valliere replied.
Cosby admitted in his deposition testimony why that never happened.
Before the trial began, Cosby said he didn't expect to testify in person and hasn't so far.
The jury also heard from sections of the deposition in which Mr Cosby confessed to giving Ms Constand pills, which he called "friends".
"Because when I said to her mother let's cut, let's talk about, her frequency raised".
These were not the words Cosby used, however.
Constand's sexual orientation has not been mentioned during the trial. One was white, one green and the third pink.
Cosby said before the trial that he wouldn't testify, but Wyatt said that could change now that the prosecution is nearing the end of its case.
The cross-examination ended quickly, with McMonagle pointing out that Cosby has consistently maintained since 2005 that Constand did consent.
Cosby's defense attorneys have sought to cast doubt on Constand's credibility by revealing she went back to his home after she twice rebuffed his sexual advances, and that she stayed in touch with him after the alleged sexual assault.
Instead, he said his "family" would write a personal check to cover the costs of Constand's education.
But Constand testified earlier this week the pills left her semi-conscious and unable to stop Cosby from sexually assaulting her. Cosby denied offering "educational trusts" to any other women he had sex with.