According to Osho, there is no real boredom in repeating stories because boredom belongs to the ego. When the 'I' relaxes, each telling is fresh: the context, the listeners, and your inner climate have shifted, so new nuances appear. Living in the present (not clinging to memory), you meet the 'same' joke newly every time, finding laughter and discovery.
When you stop clinging to your ego and just stay present, the same joke feels new each time.