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After her resurrection, Mary struggled with her new surroundings that have changed in the last three decades which caused her to briefly leave her sons. She became aligned with the British Men of Letters who helped her sharpen her skill as a hunter and better adapt to the new world though alienated her from her sons.
Redemption: Understanding Jack\n\n Taking him for a spin in the Impala and showing him the basics of living life for a day are all sensible things Dean does to help Jack acclimate. Also, when Dean listens to Jack's soul-rejuvenating revelation of unintentionally killing Mary, he actually listens and forgives "the kid."