Before the announcement, U.S. Secretary of State Mike Pompeo seemed to hint that the outcome of the talks might not be what Trump has promised in the past. "We just need the doors to be opened so we can start fresh", he said, telling Cuomo, "it's a great day" and exclaiming: "I'm so happy!"
After Trump's stern speech about North Korea's nuclear weapon program last November, Kim's government responded by calling the US president an "old lunatic" - to which Trump responded by passively calling the North Korean leader "short and fat".
The two men are expected to meet on their own for the better part of an hour, with only a pair of interpreters in the room.
The two delegations then held a working lunch where press secretary Sarah Huckabee Sanders, U.S. Ambassador to the Pilippines Sung Kim and national security council senior director for Asia Matt Pottinger joined the U.S. team.
"The senior officials of the party and government sincerely wished Kim Jong Un good successes in the first summit meeting and talks between the DPRK and the USA and his safe return", the KCNA said.
"It's wonderful, when I said those things, when I said those damn things, when I went back home I got so many death threats", a tearful Rodman told CNN's Chris Cuomo while wearing a "Make America Great Again" hat. It's aimed at settling a standoff over Pyongyang's nuclear arsenal.
After greeting each other, the two leaders planned to sit for a one-on-one meeting that a U.S. official, speaking on condition of anonymity, said could last up to two hours, with only translators joining them.
"This is Trump's natural setting - he's used to being in front of TV cameras while this might not be so natural for Kim", he said.
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"It was not an easy journey", Kim said earlier.
"It's going great", Trump said, with Kim at his side.
As the two leaders met, Singapore navy vessels, and air force Apache helicopters patrolled, while fighter jets and an Gulfstream 550 early warning aircraft circled.
However, Leong said both found it hard to hide their nervousness once they were seated, with Trump displaying a slanted smile, and fidgeting with his hands and Kim leaning and staring at the ground.
Trump has said that he would be willing to stay longer and potentially stretch the summit out over two days depending on how talks were proceeding.
He said this was again a "subtle gesture" from Trump to gain sympathy, with gentle touches to the North Korean's shoulder and back. His public statements and state-run media indicate he wants a deal to ease sanctions, but that he won't give up his nuclear weapons until he feels safe enough to retain power without them.
"Sanctions will remain until North Korea completely and verifiably eliminates its weapons of mass destruction programs".
There will not be a repeat of "flimsy agreements" made between previous US administrations and North Korea, Secretary Pompeo told reporters in Singapore on Monday.
President Donald Trump and North Korean leader Kim Jong Un are chatting over a lunch of beef short ribs, sweet and sour crispy pork, and braised codfish.