By Kylie Atwood and Kevin Liptak, CNN

(CNN) -- President Donald Trump was looking to flatter his new friend in Singapore when he struck upon an unusual compliment.

He had known plenty of people who had grown up wealthy and whose families were powerful, Trump told Kim Jong Un, the despotic North Korean dictator whose father and grandfather held the same role.

Many of them emerged messed up, Trump said. But, he added, Kim wasn't one of them.

Of course, Kim rules North Korea with an iron fist and a disregard for human rights. And his stature was gained through birth, not hard work. But Trump's choice of praise for his new negotiating partner, relayed by a person familiar with the conversation, reflects the US President's determination to flatter his way to nuclear peace in Asia.

As he embarks upon a second summit meeting with Kim in Hanoi, Trump appears poised to employ the same tactics as he seeks out a concrete road map for North Korea's denuclearization. Before the formal talks begin on Thursday, the two men will sit for a small dinner with only a select number of aides -- an intimate kick-off to a summit balanced on perhaps the world's most improbable diplomatic friendship.

"It's a very interesting thing to say, but I've developed a very, very good relationship," Trump told the nation's governors on Sunday evening before departing for Hanoi. "We'll see what that means. But he's never had a relationship with anybody from this country, and hasn't had lots of relationships anywhere."

A bond is forged

Thirty years apart in age and separated by decades of enmity between the US and North Korea, Trump and Kim have forged a bond built on mutual displays of effusive praise. In back-and-forth letters over the past seven months, each has used flowery language to describe the other and appeal to his sense of ego, a trait both men carry in spades.

The practice, which has drawn eye rolls among some of the more seasoned national security aides at the White House and the State Department, nevertheless brought the two sides to another summit meeting in Vietnam. After the two men meet for dinner on Wednesday evening, they will sit for extended talks on Thursday, including a one-on-one session with only their translators present.

Some of Trump's aides have expressed concern at what he might be willing to concede to Kim in his quest for progress on a nuclear arrangement. During last year's meeting in Singapore, Trump agreed to suspend US-South Korea war exercises, viewed as a major concession to the North that caught both Seoul and the Pentagon by surprise. North Korea experts worry that behind closed doors Trump may have promised even more, like eventually pulling US troops out of South Korea in full.

This time, however, Trump is hoping to make more tangible progress toward ridding North Korea of its nuclear weapons, explain senior administration officials. He's also competing with a narrative of scandal back home, as special counsel Robert Mueller concludes his Russia investigation and as Trump's former personal lawyer Michael Cohen testifies on Capitol Hill.

With political hostility running high in Washington, Trump will find a more favorable reception in Hanoi, where signs have been erected around the city hailing the prospects for peace. T-shirts emblazoned with the instantly recognizable silhouettes of the two bombastic leaders are for sale at shops around town. In front of the hotel where Kim is believed to be staying, a bed of roses has been fashioned into the US and North Korean flags, with two hands shaking in the middle.

That's the type of reception Trump had been hoping for in calling for a second summit, which he believes will generate the same type of wall-to-wall television coverage of the first. Some of his aides have warned him that a second go-around would capture less attention, though Trump has largely discounted that advice.

Part of the attraction, Trump believes, is the unlikely affair he's developed with Kim, particularly following a period of heightened rhetoric last year that culminated with the President boasting of the superior size of his "nuclear button."

Pen pals

After agreeing to meet, the threats cooled off, but the relationship heated up. The first sign of the budding pen-pal arrangement came when North Korea's spy chief arrived to the White House bearing a comically oversized envelope containing one of the first effusive missives.

Since then, Trump has taken to carrying around copies of his most recent letter from Kim in his coat pocket, withdrawing it to show both his friends and political adversaries. During heated talks with House Speaker Nancy Pelosi and Senate Democratic Leader Chuck Schumer during this year's government shutdown, Trump whipped out the letter and threw it on the table.

"Read this," he instructed Schumer, before flinging the document over the table in the senator's direction.

Trump has also bragged to his wealthy friends about his relationship with Kim, who is known to have adopted brutal tactics for consolidating power and who oversaw the detainment of American student Otto Warmbier, who returned to the US in a vegetative state and died soon thereafter.

"We have a terrific relationship, and we'll see where it goes. Who knows where it goes. But we'll see," Trump said in a video recorded this weekend and played at an event held for the "Trumpettes," a group of supporters at Mar-a-Lago, his private Florida club.

"The personal relationship between the leaders is important in sort of setting an overall tenor to the negotiations," said Victor Cha, a veteran North Korea adviser who was once considered to be Trump's ambassador in Seoul and is now senior adviser at the Center for Strategic and International Studies in Washington. "But having said that, when that really works is when you have two sides that are tough -- you know, negotiating very hard, and trying to align their positions."

"The gap between the US and the North Korean positions is so wide between the two sides. I mean, we can't even agree on what denuclearization is," Cha added, citing administration officials who last week told reporters there did not yet exist a common definition of the key negotiating goal. "The gap is so wide that simply having a good relationship is not going to do it."

No rush on a deal

Trump has countered that he is in no rush to execute a nuclear deal with North Korea, and the absence of missile and nuclear testing means his diplomatic gambit is working. He's attributed the pause to his personal wooing of Kim, which in Singapore included warm moments like placing his hand on Kim's back and later showing him the interior of his heavily armored limousine (to some consternation from the US Secret Service).

It was in that meeting that Trump first gauged his ability to deal with Kim in person. He had told reporters on his way there he was likely to appraise his interpersonal chemistry with Kim within the first minute of their encounter.

Asked how, Trump pointed to "just my touch, my feel."

Kim, who had caught wind of the President's comment as he made his own way to Singapore, raised the comment with Trump about an hour into their talks, according to the person familiar with the conversation.

Trump quipped back that it really only takes a few seconds to estimate a person. So what did he think of him, Kim asked. Trump offered his thoughts, including his determination that Kim was sort of sneaky -- but not too sneaky.

"But do you trust me?" Kim asked. The President said he did, and that he must trust him if they were ever to forge a deal.

Displaying a quick wit, Kim turned to Trump's national security adviser John Bolton -- a hawkish skeptic of diplomacy with Pyongyang -- and asked if he trusted him, too.

Bolton said if Trump did, then he did, too.