It will certainly be an exciting day and I know that Kim Jong-un will work very hard to do something that has rarely been done before.
Few people expect Kim to commit to what some Trump administration officials call "CVID:" Complete, verifiable, and irreversible dismantlement of nuclear weapons programs - certainly not at this meeting, and perhaps not ever.
Kim Jong Un will undoubtedly get a sense of all that as he arrives.
The short answer is nobody knows for sure.
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White House spokeswoman Sarah Sanders said United States and North Korean officials would hold working-level talks on Monday. The Canadian, Michael Spavor, ended up serving as the pair's personal interpreter.
"North Korea's increased dialogue with other countries is a positive step, but before the world gets too excited they should remember that Kim Jong Un still presides over perhaps the most repressive system in the world", he said.
Spavor did not return TIME's request for comment on the trip.
Despite this emphasis on first impressions, Trump began the Singapore summit by signaling to Kim that he's the kind of guy who refuses to put his phone down during dinner, and can't stop talking about his ex.
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Sen. Lindsey Graham said on Sunday that military force should be the "last resort" to ending the nuclear threat in North Korea, if diplomatic measures fail to make progress. "The haters, they say, 'Oh, you're giving him a meeting, '" Trump said.
Close US ally Japan has urged Trump to bring up the decades-old issue of its citizens abducted in 1970s and 1980s to train Pyongyang's spies in Japanese language and customs. "It's never going to be there again".
As anticipation for his historic summit with North Korea has ratcheted up, salesman in chief Donald Trump has done something out of character: ratcheted expectations down.
In his public statements, Mr. Trump has shown gradually greater flexibility toward North Korea, saying he viewed its disarmament as a "process", rather than something to be done all at once, and disavowing the phrase "maximum pressure", after making it the centerpiece of his policy.
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And no wonder, as it appeared to depict the defining confrontation of the weekend's Group of Seven summit, the divide between U.S. Other G7 partners also seemed stunned by Mr Trump's reaction, and pledged to support the communique.
In response to a question from VOA News just before heading to Asia from the Group of Seven summit in Canada, Trump said "I really feel confident" about the unprecedented encounter between a sitting American president and a member of the family dynasty which has maintained iron-fist control over one of the world's most reclusive countries for three generations.
Yet Trump and Kim have yet to agree even on how to define denuclearization of the Korean peninsula - the stated goal of the meeting. "Of course, the message is being delivered but in a more formal way".
The North, many experts believe, stands on the brink of being able to target the entire United States mainland with its nuclear-armed missiles, and while there's deep scepticism that Mr Kim will quickly give up those hard-won nukes, there is also some hope that diplomacy can replace the animosity between the United States and the North.
Kim's unexpected charisma - his impromptu invitation for Moon to hop across the border, and his jokey apologies about waking the President up with early morning missile tests - was so successful in rehabilitating his image in South Korea it even inspired memes and tweets comparing the dictator to a cute teddy bear. He could be seen speeding through Singapore on Sunday in a black limousine adorned with large North Korean flags. On Tuesday, both leaders will converge on Sentosa Island for their historic summit.
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