"Well I think you have what it takes too," Trump replies. "And I think everyone in this room thinks you have what it takes also."
Bridget Marks, one of the models Trump interviewed, said in a phone interview with CNN that she had a positive experience with Trump that day and whenever she has seen him since.
"I thought he was thoughtful. I thought he was respectful. I had a very good time," said Marks, a registered Democrat who said she is remaining neutral in the presidential election. "He has remembered my name and been very nice to me and my family whenever I've seen him."
Jeff Cohen, a senior photo editor for Playboy who was at the event, said that the magazine knew that Trump would create more publicity for its special edition.
"We sat around and decided, 'Let's launch the search in New York City,'" he told CNN. "Obviously, the media capital. We'll get a lot of press, we'll get TV, we'll get radio. What's the best way to do that?
"'Aha, I know, we're gonna ask Donald Trump whether he would come and photograph, do the test pictures, of the first girl that comes in.'
"And that's basically what we did."
Trump also appeared briefly in a 2001 Playboy video, which featured a Betsey Johnson fashion show. He appears backstage, alongside two Playmates and his current wife and then-girlfriend, Melania Knauss.
The Trump campaign did not respond to a request for comment from CNN.
Trump has long struggled to win support from female voters - something seized upon by Democrats.
Hillary Clinton, his Democrat rival, brought up comments about Alicia Machado - a former Miss Universe - in the first debate, reminding him how he demeaned her by referring to her as "Miss Piggy" and "Miss Housekeeping" - for her Latina roots.
He later launched into a bizarre tirade against her. Clinton said it showed he was "unhinged".
The latest CNN/ORC poll, conducted after the first debate, found that 62 per cent of women viewed Trump unfavourably.