While both sides had a lot to say, the Republican particularly had a tough time with toning down his vicious attacks that have made headlines during the presidential debates as he struggled with the self deprecating humor that are a common occurrence at the dinner.
That joke got a big laugh, but Trump was also jeered for several lines that began with calling Clinton "corrupt", then saying she was "pretending not to hate Catholics" and another joke about the Clinton Foundation's work in Haiti. "The audience more or less accurately, I think, reflects the sentiments that are going on".
Ms. Clinton roasted Mr. Trump for his tendency to grade the physical appearance of women.
During a debate with Clinton on Wednesday night, the NY businessman reiterated his assertion that the election is being rigged against him and refused to commit to accepting the outcome of the election if he loses.
Trump planned to lay out his closing arguments for support with a speech Saturday in Gettysburg, Pennsylvania, focusing on the priorities for the first 100 days of his presidency. "I don't know why", he quipped.
The private moment at an annual Catholic fundraiser in NY was a rare departure from the unsympathetic tone both candidates have struck toward each other in a campaign that has been dominated by deeply personal, no-holds-barred attacks. "After listening to your speech I will also enjoy listening to Mike Pence deny you ever gave it".
"If it's a fair outcome, he will absolutely accept it".
Trump and Clinton sat one seat apart for the evening, with New York's Cardinal Timothy Dolan the only buffer.
She said that America knows "the difference between leadership and dictatorship".
Dolan said he was "very moved by the obvious attempt on behalf of both Secretary Clinton and Mr. Trump to kind of be courteous, to get along, to say nice things privately to one another".
Trump, who has been lagging in opinion polls, has offered no widely accepted evidence to back up his claims of vote-rigging.
Fanning those flames, Russia's government has asked Oklahoma and two other states to allow Russian officials to be present at polling stations on Election Day, to study the "US experience in organisation of voting process".
Trump told an earlier rally in Fletcher, North Carolina, that he wanted to have no regrets about whether he worked hard enough to win the election, and urged followers to get out to vote.
"So, we've adjusted our schedules to make sure that our girls are first, so while he's traveling around, I do day trips".