In his appearance on Fox Business Network, Schilling went back and forth with Regan about Trump's comments.
'The conversation you're having about the things he said about the 10-year-old girl, to me, is at the very heart of why this is a problem,' Schilling said.
'How many times - and I have three boys and a daughter - how many times have you looked at a young man and said, "Wow, is he going to be, he's a beautiful young man.
Wow, he's a gorgeous young man," and that man was 12, 13, 14, 15?'
Regan replied: 'I'll be honest, Curt: zero.'
'Now, see, that's a lie,' the former pitcher said. 'There's no way you haven't seen someone else's son and said, 'Wow, he's beautiful'.'
'You're alone on this one,' the news anchor replied.
'I don't look at a young boy and say in 10 years I'm going to date him,' she said. 'I just don't. I think that would be pretty sad if I did.'
Regan asked Schilling if he has ever looked at young girls and said he would date them in 10 years.
'No, no. I have a daughter, my daughter has friends. I've seen my daughter's friends, I'm a man. 'Wow, she's a beautiful young lady.' I don't immediately jump to molesting her.
But that's where the left has gotten...'
When Schilling commented to Regan that she may have said things in her life that she later regretted, the anchor replied that it's a recurring theme with Trump.
In the last 24 hours, six women have come forward to accuse Trump of touching or kissing them inappropriately, just days after the Republican nominee told Anderson Cooper that he had never kissed or groped a woman without their consent.
The allegations were made just days after Trump was overheard on a hot mic talking about making unwanted advances toward women.
In a 2005 interview with Access Hollywood, Trump was captured on audio saying to host Billy Bush: 'I'm automatically attracted to beautiful women - I just start kissing them. It's like a magnet.'
'Just kiss. I don't even wait. And when you're a star, they let you do it. You can do anything.'
He said in the wake of the tape's release that his comments were nothing more than 'locker room talk.'
In May, Schilling announced that he's endorsing Trump.
In an essay that he published on his blog 38 Pitches, Schilling wrote that he trusts the billionaire businessman, noting: 'I don't agree with him on many things, that's cool.'
'I also know that there is and never will be a candidate anywhere that I will agree with on everything. That candidate doesn't exist.'