A group of mostly elderly South Koreans travelled to a tourist resort in the North for the event, the first such reunion for three years.
"I've prepared for him some household medicine including digester and headache pills, nutritional supplements as well as some daily necessaries", Lee Soo-nam, a 76-year-old South Korean, told Reuters before meeting his older brother in the North separated by the war.
"When I escaped the war..." she said, unable to continue, apparently overwhelmed by regret over the fact that she had to leave her two daughters behind.
But the reunions are often also tinged with frustration, with many North Koreans determined to publicly demonstrate their allegiance to the regime, out of genuine loyalty or just fear.
The first group meeting will be followed by a dinner hosted by the North Korean side from 7-9 p.m.
Lee Geum-seom, 92, wailed as she laid eyes upon her son, Ri Sang-chol, 71, for the first time in over 60 years, pulling him to her chest as she cried, "Sang-chol!" Her son, Ri Sang-chol, shed tears of joy as he pulled out a picture of his now-deceased father.
Kim Gyong Sil and Gyong Yong (72) and (71), wearing light violet traditional dress of hanbok, stood nervously staring at the entrance before their 99-year-old mother Han Shin-ja turned up. On one hand, I'm sad that I won't see my brother.
"I remember how lovely you were", Cho Hye-do told her big sister.
"I am very glad that I have been selected this time, I'm walking on air now". "You really look exactly like me".
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Dok-yo sobbed, "I can't recognize you, either". Kim Dal-in, 92, asked his sister, Yu Dok, Reuters news agency reports. "I'm so glad that time has finally come".
The event, which is facilitated by the Red Cross, is the outcome of a historic meeting between North Korea's Kim Jong-un and South Korean President Moon Jae-in at the border in April.
But negotiations to plan the reunions were sometimes rocky.
"It is a shame for both governments in the South and the North that numerous families have passed away without knowing whether or not their lost relatives were alive", South Korean President Moon Jae-in told a meeting with presidential secretaries Monday.
The elderly and about 300 others embarked on a trip to North Korea around 8:30 a.m.in 27 buses from Hanwha Resort in the South's northeastern coastal city of Sokcho, where they had spent the previous night. The two sides have yet to resolve that issue.
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Six doctors and almost a dozen nurses will travel to attend to the elderly group during the reunion and a makeshift emergency medical centre will be on duty around the clock.
North Korea has shifted to diplomacy in recent months.
She could only say "Ah" and "When I fled." before choking up with tears.
The first face-to-face family reunions organized by the two Koreas were in 1985, though they didn't resume until 2000.
The reunions highlight the stark differences that remain between the two countries.
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South Korean Je-keun tried to explain that the Korean War took place because North Korean leader Kim Il Sung invaded on June 25, 1950.