1) Jiraiya did not set out to be a legendary ninja and a famous author, but he would not have said no to either if you'd asked him.
2) In actuality, all Jiraiya wanted when he was a small child and studying to be a ninja was to be More Than Normal or at least Better Than Average.
3) For a few days when he was nine, Jiraiya wanted to be Hokage. This dream ended when he told Tsunade about it and she smirked and explained to him what hard work it was. Nobody in their right mind, she said, would want to be Hokage. Neither of them caught the unconscious fondness in her voice when she said that she wasn't all that sure he was in his right mind after all, though.
4) Jiraiya loved his parents very much, even though his snake-eyed orphan teammate taunted him for it.
5) When Jiraiya was ten, his parents died in a battle, prompting him to fumble with ink and a scroll until a rambling, disorganized poem about grief and loss came out through his fingers. He showed the poem to his teammates and teacher the next day, and they cared enough not to laugh.
6) He can't remember a time when he didn't think Tsunade was pretty (even if at age seven he'd have never admitted it, because she was a girl) and Orochimaru was annoying (but the smartest in the class and somehow it was an honor to wind up on his team).
7) Jiraiya was the first of his team to train genin students. When he rushed to his teammates with the news of his new assignment, Tsunade rolled her eyes but smiled a little, and Orochimaru deigned to look up from his studies long enough to remind Jiraiya that he'd only make a mess of it anyway.
8) When two of his three students died in combat, Jiraiya spent the next two weeks locked up in his house. His teammates visited to bring him food and remind him that he still had companions in this world, but they had little effect. Orochimaru was sorely disappointed that Jiraiya did not notice the effort that had gone into the meal he'd made.
9) Jiraiya had written a short story before, after Tsunade's brother died, but he hadn't shown that one to anyone. It wasn't until after his students died that he wrote a full book. He did it in those two weeks that he spent pent up inside, scrawling so swiftly and passionately that when he reread it, he sometimes had to guess at what characters he'd written. He meant it to be a great work of literature, but after the first few attempts to begin such a daunting task, he gave up and wrote a feel-good story about a down-trodden young man who rose from rags to riches and had plenty of fun with many blond ladies along the way.
10) When he finally emerged from his self-imposed imprisonment, his remaining student smiled at him and promised to make things better. Jiraiya had the decency not to laugh.
11) When Orochimaru first left, Tsunade had to pick Jiraiya up and carry him over her shoulder to prevent him from running off after his teammate immediately. After that, when he went to retrieve Orochimaru, it was in an orderly fashion, and he went home empty-handed with equal parts resignation and bitterness.
12) Jiraiya was the last of his team to leave the village. When Orochimaru and Tsunade left, he felt he'd been set adrift, like a freed kite. Kites, he noted in an overwrought metaphor in one book, were not meant to be freed. He was quite detached and calm when he wrote this. It wasn't about him.
13) He had been writing for a while by that time, but he did not start actually publishing until he was on the road.
14) There was a period of a few years during his wanderings when Jiraiya found himself forgetting every name but his own and his teammates'. He even forgot his own pseudonyms unless he kept a list handy.
15) Jiraiya did not meet his student's students, his own grand-students if you want to take the relationship that far, until the Fourth's funeral, and by that time there was only one left, a boy who reminded him too much of a silver-haired version of Orochimaru. Jiraiya left early.
16) At one point, he met Orochimaru's student. She reminded him too much of himself, Orochimaru, and Tsunade combined for him to be comfortable hitting on her (although he did consider it), but somehow she managed to charm his wallet away from him anyway. And his pants. He still isn't sure how that happened.
17) In all the years he wandered, Jiraiya only ran into Tsunade three times. Two of those times were fairly early on. Afterwards, he learned to avoid towns with sizable gambling halls, and he rarely even saw her, much less spoke with her. The third time, they both wound up in a pissant northern border town during a heavy snow, and they were trapped in the same inn for three days. They had tea in weary, uncomfortable silence.
18) When he first met Naruto, Jiraiya refused to be reminded of himself. It took some effort. Fortunately he was familiar with the state of denial. For instance, by the time he met Naruto, Jiraiya had convinced himself that he didn't love Tsunade and that he'd never cared for Orochimaru. On his good days, anyway. Sometimes it didn't work.
19) It took him a while to remember that what he felt sometimes around Naruto was pride.
20) Some days Jiraiya doesn't know whether to smack Naruto or thank him.
Coming Soon: Team 7, Temari and Shikamaru, Hatake Kakashi, and Rock Lee.