An Impossible Choice: The Pain Within Tsunade's Heart

is episode 89 of the original Naruto anime.

Synopsis
Naruto is tasked with combining the spinning and the power developed in the previous steps, something that Jiraiya cannot help him with. As he attempts to do both, Orochimaru asks Tsunade to heal his arms, the Third Hokage's sealing of them bringing him excruciating pain and making them unusable, leaving him unable to use techniques. Although she has no intentions of helping Orochimaru due to his killing the Third, Tsunade decides to consider the matter when he offers to revive her dead brother, Nawaki, and lover, Dan. Orochimaru gives her a week to think about it, and he leaves.