A/N: Wrote this as a request, so this little oneshot is dedicated to that person. All dialogue was taken directly from the manga. Hope it's enjoyable!
Disclaimer: Naruto (c) Kishimoto, not me.

Theirs was a relationship of rituals. When, at the age of ten, Jiraiya had first asked his flat-chested teammate out on a date, neither of them could have imagined that that question would become the mould that shaped their relationship.

He had spent his youth chasing after Tsunade like a love-sick puppy, foolish and innocent enough that his feelings pushed him like a leaf in the wind - and she would invariably refuse. He figured that if he tried hard enough, long enough and kept asking until he was either out of breath or out of bones for her to break, then she would have to come around and accept him as more than a teammate.

Friendship did grow between them, eventually. As always, he had asked her out and she had declined - all their interactions started the same way then -, but had somehow found himself sharing a cup of tea with her afterwards anyway. That had been a turning point, and it became the first of many encounters that brought them closer throughout adolescence.

Jiraiya's hopes had swelled and his heart fluttered at the thought that she was finally warming up to him. Their teamwork was better than ever and the occasional afternoons they spent sitting together and supporting each other after a rough mission, talking about any and everything, were among some of his fondest memories. He still asked her out, but she wasn't as vehement - or violent - in her refusals anymore.

And then she had met Dan.

Jiraiya remembered smiling when she had introduced them to one another. He had smiled so hard that his cheeks had permanently creased. He took to traveling at that point, and if at the time he excused himself with his restless spirit, now that he was older he could say with nothing more than a tinge of regret that it had been his inability to see Tsunade happy with another man that had drove him away from Konoha. The crowds of women he drowned his sorrow in did not heal his broken heart, but they did numb it enough that when Tsunade announced her engagement, he could smile and mean it again. He kept asking her out, but only when Dan was present - and if Tsunade realised that there was more in it than just an affectionate joke between old friends, she never said anything.

Ironically, it wasn't until Dan was gone that Jiraiya stopped asking the question. Tsunade had been so devastated that he could not in good conscience keep doing it, knowing all the memories he would be evoking. He buried all the feelings he had for her once more - they were so deep in now that even he could not extricate them -, and became the epitome of the good friend as she gambled away her sake-drenched grief. Then it finally became too much for her and she walked away from the village and him. Over a decade passed until he saw her again.

Their reunion was neither awkward nor remarkable, circumstances aside. Their relationship had picked up where they had left off, as two good friends - one of whom had made a life-long promise to look after her whenever allowed.

He didn't always ask the question now, but Tsunade still let him know that he would have to be the last man on earth before she even considered going out with him.

That day, Jiraiya crossed the threshold of the door into Tsunade's office, nonchalant as ever, and asked her out. He had sensitive information for her and, while the Hokage Tower with its tight security was frankly the better place in which to deliver it, he was feeling selfish. For once, he wanted her to accept and maybe that slight manipulation would do the trick.

She didn't, but they ended up drinking and talking and reminiscing anyway, and it wasn't until the time came for him to leave, that he realised that he had failed. They had yet to break their cycle.

Selfishness roared inside him then, but he clamped it down, thinking there would always be a next time. If neither he nor Tsunade were going to break their routine, then no one - Akatsuki leader or not - was going to do it for them. He almost had his fears subdued, when something in the script of their unwritten play changed.

Jiraiya looked up, surprised and unsure whether he had heard her correctly. Tsunade continued speaking, though, confirming it for him.

"If I lose you on top of everything... I..."

And never had she looked so exposed, so frail, as she did then, sitting on that bench in the middle of the street with her cheeks flushed from too much sake and her sleeve dirty with bile.

Her open concern was a decisive change to the pre-established order of their relationship, but change could always work both ways - for better or for worse. Caught unprepared, Jiraiya gave the only response he could to ensure that she would be there for his next round of rejection.

"You'd cry for me? That's nice to know," he laughed. "But I doubt you'd cry as much as you did for Dan..."

"You fool!" she grumbled, glaring at the concrete floor in annoyance.

The insult barely registered with the old Toad Summoner. Instead, he was beginning to wonder if perhaps the right time for Tsunade to quit on her end of the game had indeed come. She had finally gotten over her grief for Dan and given up on her attempts to lose herself in the flashy world of gambling. At the same time, due to her position as Hokage, she was learning once again how to rely on others, including Jiraiya, who was Konoha's number one intelligence gatherer when it came to Akatsuki.

"Then how about we make a gamble of it," he proposed, intending to test how serious she was. She glanced at him from the corner of her eye then. "You can bet that I'll die, since there's no way you'd ever win a bet."

She looked so shocked, so horrified by his indirect admission that he was feeling uncertain about his mission too, that Jiraiya had to close his eyes and look the other way.

"And in return, when I make it back alive..."

Before he could say another word, the sheer selfishness of that statement hit him and he cut himself short. He should have kept to his usual lines and not have said that. He should not have opened that door now, when he had no idea of what would happen to him. Despite all his boasting, he was not as young anymore and he would hate himself if he broke the silent promise he had made to her all that time ago, if he fed her hopes that were doomed to be dashed.

No, his Slug Summoner was right. She had lost too much, seen too many people she cared about die. It would not do to add one more to that list. He would talk to her when he returned safe and sound. He would ask her on a date again and they would have a chance to open this door then without the possibility that he might leave her alone hanging over him.

So he laughed it off again and steered the conversation back towards safe grounds. Time had tempered their relationship enough that a few weeks' difference would not matter - they could always break their routine next time.