Donald Trump has spent days this week broadcasting his desire to meet with North Korea’s Kim Jong Un as early as this year. But rekindling their “bromance” and turning these hopes into an actual return to talks will prove a daunting task for the U.S. president.

Trump’s recent order to curtail an annual large-scale joint military drill with South Korea— which he labeled “totally inappropriate and hostile” to North Korea — was a clear sign of his determination to restart dialogue with Pyongyang, according to longtime observers.

“He is most definitely keen on reengaging with the North Korean leader,” said Evans Revere, a former U.S. State Department official who has extensive experience negotiating with the North. “But the decision is also the latest manifestation of Trump’s tendency to make risky, even dangerous, unilateral concessions to North Korea as he seeks to create the illusion of progress with Pyongyang.”