A night after they delivered broadsides galore against each other in a final debate, Hillary Clinton and Donald Trump had the opportunity to deliver some good natured campaign barbs at each other at a historic New York dinner, but instead after a few funny lines, their speeches veered off course, resulting in some awkward moments, broadcast live on television.
Trump started off his remarks at this Catholic charity event in New York by poking some fun at himself, telling the audience that "modesty is my best quality" - then he moved on to Clinton, noting that the 1,000 people in attendance was unusual for her.
"Hillary calls it her largest crowd of the season," as the crowd at the historic Alfred E. Smith dinner laughed.
But after a few more lines that drew applause, Trump's speech turned abrasive, as he called Clinton corrupt, and was then met with boos, hissing and catcalls as his jokes turned into real jabs.
When Clinton's turn came, she also began with some funny lines about herself - "Usually I charge a lot for speeches like this," as well as one that made fun of her campaign schedule.
"This is such a special event - I took a break from my rigorous nap schedule to be here," Clinton said with a smile to more laughter.
But as Clinton kept going, some of her later lines about Trump began to take on more of a negative tone, as she was then met with near silence in the room, along with some open grumbling from the audience - as this night of laughter could not escape the realities of the 2016 campaign.
"She blew a chance to look more Presidential," said one of my followers on Twitter.
Maybe it should not have been a surprise, but it would have been nice to see an evening like this - historic in many ways in American political history - rise above the tenor of the 2016 race.
Both Trump and Clinton would probably have been well advised to speak for a few minutes, make a few jokes at their own expense, and then move on.
But it didn't happen that way.
Only 18 days left.