USA and North Korean officials are meeting Monday at the Ritz Carlton in this island city-state to negotiate before a sit-down meant to settle a standoff over Pyongyang's nuclear arsenal.
For the North, Kim Jong Un has already won a huge propaganda bonus by merely having the summit and sitting down as an equal with the US president, an accomplishment his father and grandfather sought but could never realize.
President Trump and North Korean leader Kim Jong Un arrived in Singapore Sunday ahead of a highly anticipated summit.
U.S. and North Korean negotiators met in a Singapore hotel on Monday, seeking to clarify the shape of Tuesday's summit, where Trump has said he intends to guided by instinct. Some experts, including CBS News' Bob Carlin, have said it could take as long as 15 years for North Korea to completely wind down its nuclear and missile program, which is estimated to include enough material for 25 to 30 nuclear weapons.
Kim later met Singapore Prime Minister Lee Hsien Loong and was seen to be smiling broadly during the encounter.
Authorities have beefed up security around the hotels where Trump and Kim (Saint Regis) will be staying.
Trump has said he hopes to win a legacy-making deal with North Korea to give up its nuclear weapons, though he has recently sought to manage expectations, saying that it may take more than one meeting.
Massachusetts Sen. Ed Markey, the ranking Democrat on the Senate Foreign Relations' subcommittee dealing with North Korea policy, said on "Face the Nation" Sunday that there's a "vast gulf" between the USA and North Korea's definition of what "denuclearization" actually means. He told Lee: "We've got very interesting meeting in particular tomorrow, and I just think it's going to work out very nicely".
Aboard Air Force One en route to Singapore, Trump tweeted, "I look forward to meeting [Kim] and have a feeling that this one-time opportunity will not be wasted!"
Later, Kim met with Prime Minister Lee Hsien Loong at Lee's office in the sprawling palace known as the Istana.
Like the real-life leaders, fake Kim and Trump are no strangers to controversies of their own. "If diplomacy fails, will you support my efforts to authorize the use of military force as a last resort to convince North Korea and China things will be different this time?" This has included backing away from an original demand for North Korea's swift denuclearisation.
Such a meeting was unthinkable just months ago when Trump and Kim were exchanging insults and threats that raised fears of war in the region.
Earlier in the week, Trump also said he has done little preparation for the meeting, noting that the meeting would be all about "attitude".