The talks in Panmunjom, the truce village in the Demilitarized Zone that divides the peninsula, came after the North's leader Kim Jong-Un indicated in his New Year's speech that he could send a delegation to next month's Games in Pyeongchang in the South.
Seoul responded with an offer of a high-level dialogue, and last week the hotline between the neighbours was restored after being suspended for almost two years.
Seoul's five-member delegation, led by unification minister Cho Myoung-Gyon, travelled to Panmunjom in a convoy of vehicles, passing a group of well-wishers holding a banner at a checkpoint leading towards the DMZ.
Looking businesslike, Cho and Ri shook hands at the entrance to the Peace House, the building on the southern side where the discussions were being held, and again across the table.
In accordance with standard practice in the North, Ri wore a badge on his left lapel bearing an image of the country's founding father Kim Il-Sung and his son and successor Kim Jong-Il. Cho also wore a lapel badge, depicting the South Korean flag.
Cho told him that Seoul believed the Pyeongchang Games "will become a peace Olympics as most valuable guests from the North are going to join many others from all around the world".
"The people have a strong desire to see the North and South move toward peace and reconciliation," he added.
It was a radically different tone from the rhetoric of recent months, which have seen Kim and US President Donald Trump trade personal insults and bellicose threats of war, while Pyongyang has launched missiles capable of reaching the US mainland and carried out its sixth and most powerful nuclear test to date.
If the North agrees, one of the top agenda items will be whether the two Koreas' sportspeople make joint entrances to the opening and closing ceremonies, as they did for Sydney 2000, Athens 2004 and the 2006 Winter Games in Turin.
The size and membership of the North Korean delegation and their accommodation -- widely expected to be paid for by Seoul -- will also be discussed.
With only two winter sports athletes qualified, North Korea is likely to bolster its presence by sending significant numbers of cheerleaders to the Pyeongchang Games, which run from February 9 to 25, analysts say.
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