1. Fuuko Shizuka: The village chief of Fuuko Village, Fuuko Shizuka, had a happy life despite not being from one of the five major ninja villages. She once sparred with the powerful Jiraiya to test her skills, but realized she couldn't match his strength. She agreed to marry him on the condition that he lived in her village, but Jiraiya declined due to his responsibilities in Konoha Village.

2. Shiguma: Shiguma worked as a waitress in a hotel in Amegakure Village. When Jiraiya visited the village, he met Shiguma and found her name interesting as it was similar to his old friend Tsunade.

However, he didn't have time to stay and left quickly.

3. Mei Terumi: Mei Terumi, the Fifth Mizukage of Kirigakure Village, is known as the "number one anime sister" among Naruto fans. Despite her stunning appearance, Mei is constantly pressured by her family to marry. While she is attracted to handsome Uchiha clan members, someone like Jiraiya might be what she truly needs.

4. Orochimaru: Orochimaru, once a close friend of Jiraiya, became a rogue ninja due to his obsession with forbidden jutsu. Jiraiya couldn't prevent him from choosing this path and it tormented him.

It remains uncertain if Jiraiya would have teamed up with the repentant Orochimaru.

5. Tsunade: Jiraiya's true love was Tsunade. He never married and rejected Fuuko Shizuka because of his feelings for Tsunade. Their final conversation implied that Tsunade had accepted his feelings, and they might have married upon his return. However, Tsunade was devastated when she received news of Jiraiya's death.