Naruto Villain: Orochimaru

Although Orochimaru was another teammate of Tsunade's, the two didn't appear to have strong bonds. When they met years later, after Orochimaru had tracked her down, their relationship had grown even more strained. He sought out his former comrade primarily for her medical prowess; Orochimaru wished to have Tsunade heal his arms after a seal had been set on them by the third hokage, and in exchange, he offered her the revivals of both her brother and her boyfriend. Though it was a large dilemma for Tsunade, she eventually chose to decline which resulted in a physical beatdown for Orochimaru.