"A couple days ago they said we would like to talk, and I said, so would we, but you have to de-nuke, you have to de-nuke. So let's see what happens," Trump said at the Renaissance Washington Hotel to more than 600 attendees, including journalists. "Maybe positive things are happening, I hope that's true ... We will be meeting and we'll see if anything positive happens."
Trump said: "I won't rule out direct talks with Kim Jong Un, I just won't. As far as the risk of dealing with a madman is concerned, that's his problem not mine."
After the 35-minute talk, the White House didn't say whether the president was joking.
In the past, Trump has said he's willing to talk to the regime's leader but the nation must commit to getting rid of its nuclear arsenal.
In October after Secretary of State Rex Tillerson revealed in Beijing that the United States had "lines of communication," but posted on Twitter: "I told Rex Tillerson, our wonderful Secretary of State, that he is wasting his time trying to negotiate with Little Rocket Man. Save your energy Rex, we'll do what has to be done!"
South Korean President Moon Jae-in announced Sunday he will send a special delegation to North Korea on Monday to discuss inter-Korean relations and possibility of dialogue between Washington and Pyongyang.
U.S. Vice President Mike Pence was planning a secret meeting with representatives of the regime at last month's Winter Olympics in South Korea, including Kim Jong Un's sister. But the North Koreans pulled out of the planned session.
"North Korea dangled a meeting in hopes of the vice president softening his message, which could have ceded the world stage for their propaganda during the Olympics," said Nick Ayers, Pence's chief of staff.
Pence attended the Gridiron Dinner, a white-tie affair, with several cabinet and family members.
Trump told the attendees that he calls Pence "the apprentice," and vice president "wakes up every morning and asks, has he been impeached yet."
Trump, returning from his resort Mar-a-Lago in South Florida on Saturday after a meeting with big Republican donors, poked fun of himself, saying "I told them not to worry, nobody does self-deprecating better than I do.
"So, who's going to be the next to leave? Steve Miller, or Melania? That's terrible," Trump said. "But you love me right, honey? She said, behave! By the way she has been an incredible first lady."
He continued: "I want to apologize for running a little late, as Jared could not get through security."
And he said he offered Attorney General Jeff Sessions a ride to the dinner, but "he recused himself."
Sessions, who was criticized by the president this past week on Twitter, was seated at the head table near Trump.
All presidents since 1885, except for Grover Cleveland, have accepted the club's invitation to attend at least one annual dinner. The entertainment includes comedy/song sketches form media members.
Last year, Trump didn't attend the Gridiron Club nor the White House Correspondents Association annual event.
In Trump's first post Sunday on Twitter, he tweeted: "The Gridiron Dinner last night was great fun. I am accomplishing a lot in Washington and have never had a better time doing something, and especially since this is for the American People!"