Asked how long it would take for him to work out if Kim was serious about striking some kind of peace deal, Trump replied: "I think within the first minute I'll know".
By giving Kim the respect that comes with interaction on an "equal footing", Trump has front-loaded symbolic expressions of his intent to improve relations, end the Korean war, and reduce military tensions on the peninsula - presumably in return for North Korea to indicate their intent to denuclearize.
"That takes a great deal of work, a great big commitment on the part of North Korea as well, and there'll be a parallel set of security assurances that are also big and bold and different", the top USA diplomat said. And if I think it won't happen, I'm not gonna waste my time - I don't want to waste his time.
Questions remain about what a deal on the North's nuclear weapons would look like.
His administration had previously suggested its goal is for Kim to immediately denuclearize, but Trump in recent weeks has appeared to scale back his expectations for the meeting. "It will never be there again", the president said.
The incident came just days before the city-state hosts high stakes talks between United States and North Korea's leaders.
Tuesday will mark the first time a sitting USA president and a North Korean leader meet, though it's unclear what a nuclear deal with the isolated country will look like.
"I think it would be an asset to have Russian Federation back in, it would be good for the world".
"For Koreans, this is a very historic moment", said politics teacher Lee Deok-hyoung, who works at the Singapore Korean International School.
Plainclothes police and the Singapore Army's Explosives and Ordnance Disposal unit were seen working to prepare for a high-security event.
"The situation was much more shocking than I had expected", he said. "There's probably an even better chance it will take a period of time".
His father was born in North Korea and escaped as a young child and the pair are hopeful the meeting could pave the way for reunification between the two Koreas. Trump said what matters more is the "attitude" he and Kim have going into the meeting.
Howard X, who declined to give his real name, told Reuters he was detained for two hours and questioned for around 30 minutes when he arrived in the early morning hours at Singapore's Changi Airport. "But certainly if it goes well", Trump told reporters during a joint press conference with Japanese Prime Minister Shinzo Abe.
"We would win that war thousand times out of a thousand", he said. Libyan leader Muammar Gaddafi was later driven out of power and killed in 2011 during the Arab Spring revolution, a fate not lost on the North Koreans.
The Dow Jones Industrial Average extended its winning streak Friday, as investors shrugged off trade worries at the start of the G-7 summit between the USA and allies.