Hyon Song-wol was feared dead after her on-again-off-again relationship with the dictator broke down, first during the mid-2000s and then again in 2012 or 2013.
But despite claims she had been killed by firing squad, Hyon has re-appeared this week in the border peace village of Panmunjom, located in the demilitarised zone separating the rowing states.
She was the only female official present at the high-profile talks discussing the possibility of North Korean athletes, supporters and officials visiting the South during next month’s Winter Olympics.
She was pictured sitting with South Korean chief delegate Lee Woo-sung, along with other officials from both sides of the border.
Like many high-profile characters in North Korea, details of her background are shrouded in secrecy.
She achieved fame in the hermit state as a singer for a North Korean pop group – along with Kim’s eventual wife Ri Sol-ju.
She then began dating Kim during the mid-2000s although disapproval from his father Kim Jong-il ended the relationship.
When Kim Jong-il died his son re-started the relationship, although it once again ground to a halt soon later.
Rumours then began to swirl Hyon had been killed by firing squad, with state-run newspaper Chosun Ilbo even appearing to confirm her death in August 2013.
A source told the newspaper she was killed along with a group of other musicians.
He said: “They were executed with machine guns while the key members of the Unhasu Orchestra, the Wangjaesan Light Music Band and the Moranbong Band as well as the families of the victims looked on.”
Some members of the group were accused of making pornographic videos although this was disputed by experts including Professor Toshimitsu Shigemura of Tokyo’s Waseda University.
He said: “If these people had only made pornographic videos, then it is simply not believable that their punishment was execution.
“As Kim’s wife once belonged to the same group, it is possible that these executions are more about Kim’s wife.”
Hyon had been spotted several times since then but the veracity of these sightings are almost impossible to confirm.
However this week’s photographs of the Winter Olympics negotiations leaves little doubt Hyon is alive, well and in a position of power within Kim’s inner circle.