At one point, Fallon admitted he was surprised when Trump backed the authenticity of President Barack Obama's tears last week. Obama announced new executive actions on gun-control policy and cried while discussing the 2012 Sandy Hook Elementary School mass shooting, in which 20 young children were slaughtered.
A number of conservative critics suggested that Obama had either faked or exaggerated his emotions, but Trump said Obama was likely "sincere." The Republican presidential front-runner repeated that belief to Fallon on Monday.
"No, I thought it was real. I disagree with what he's doing. I disagree with many of the things he's done. But I thought that was heartfelt. I thought that was real. And it's a tough situation. We're in a tough situation. But we have to protect our Second Amendment. Very important," he said.
Fallon then asked Trump: "Do you cry ever?"
Trump replied: "Yeah, when I was one [years old.] I cried."
Fallon and Trump also conducted a mock job interview, in which the comedian asked Trump questions about his strengths and weaknesses.
"I'm an extraordinarily handsome person. I have a beautiful head of hair. I was always a good student and I always worked hard," Trump said.
"This is a high-profile position. Is media attention something that you would be comfortable with?" Fallon asked.