1. Orochimaru and Tsunade: Orochimaru and Tsunade were childhood friends who studied ninjutsu under the guidance of the Third Hokage. Orochimaru was once handsome and not obsessed with forbidden jutsu. Tsunade was initially attracted to Orochimaru's looks and talent, but his lack of romantic interest caused her to lose interest over time.

2. Jiraiya: Jiraiya became Tsunade's lover as they grew up. Jiraiya deeply loved Tsunade and shared the dream of becoming Hokage with her younger brother.

Sadly, Jiraiya died in battle during the war, which sent Tsunade into despair. It wasn't until Naruto entered her life that Tsunade found a new purpose and eventually became the Fifth Hokage.

3. Fourth Raikage: The Fourth Raikage had a strong connection with Tsunade and sought her help when one of his subordinates was injured. They fought together against Kabuto and Naruto. Their straightforward and bold personalities made them a great match.

However, their positions prevented them from pursuing a romantic relationship, which might have preserved the Senju clan bloodline.

4. Jiraiya's unrequited love: Jiraiya loved Tsunade his whole life, but she rejected his advances. Despite his carefree lifestyle, Jiraiya's heart belonged only to Tsunade. He never married or had children. Tsunade had planned to accept his confession, but Jiraiya tragically never returned.