Let's say that Jiraiya gives Naruto a full explanation for just why he is such a dirty old man early on in his training. Rather than it being for purely practical ninja reasons, it instead reflects Jiraiya's very philosophy on life:
And thus, hilarity ensues. Discuss!
Naruto: Geez Ero Sennin, do you have to stare at every pretty woman around?
Jiraiya: OF COURSE I DO! To not do so would be an insult!
Naruto: What?
Jiraiya: Really Naruto, think about it! All these pretty girls are pretty for a reason. They put an enormous amount of effort into being pretty, by working out, training, taking care of their skin and hair, and dressing right! They WANT you to look, to appreciate them! To not look makes you look like a total coward, or that you have something on your mind other than them! It's an insult!
Naruto: Well... I guess... But-But it still wrong!
Jiraiya: Says who?
Naruto: ... Says... Says everybody!
Jiraiya: Well, not everybody is me. Did you know, all the best ninjas are dirty old men or women at heart?
Naruto: Really?
Jiraiya: Of course! You knew old Sarutobi! He was one of the dirtiest old men in the history of Konoha! And he lived well into his eighties for the simple reason that he didn't let those naysayers and killjoys prevent him from appreciating pretty girls! All this stress over not being able to look or compliment a girl can be killer!
Naruto: Seriously?
Jiraiya: Seriously! Look at me: I'm in my sixties but I'm no pushover! It is because I don't let the stress of some fuddy duddies too cowardly to appreciate the beauty around them get to me! I look and all are enriched by my looking because they know I have nothing to hide!
Naruto: Wait... Don't you?
Jiraiya: Yes, but as it usually doesn't concern them it doesn't make them worry, and that makes it easier to accomplish a mission when the people around you are not on their guard.
Naruto: Wow... Wait, what about Baa-chan?
Jiraiya: *smirks* Oh, don't let her fool you. She's tried to be a fuddy duddy herself, but she eyes the male eye candy just as often as I do the female-And even other females.
Naruto: *blush* S-Seriously?
Jiraiya: Seriously! Why do you think she has Shizune go around without underwear?
Naruto: What?! Nee-chan doesn't wear underwear?!
Jiraiya: Not the slightest bit of cloth between her nethers and the air.
Naruto: Woah... So... Orochimaru?
Jiraiya: HA! He tried to be a dirty old man but he could never quite manage! Got too locked up in immortality and binding shadows in the dark. *sighs* It is the saddest thing in the world when a man becomes so obsessed with not dying, or some other goal that he can't take a moment to look around and appreciate the beauty in every day life. If you stop doing it, you just start turning more and more to bad things.
Naruto: Oh man...
Jiraiya: Trust me Naruto, it's far better to be a dirty old man or woman at heart! Far less stressful, and far more honest! And as ninjas, honesty is at a premium. And with all the benefits, like making a girl feel special, making the people around you feel at ease, and making yourself less stressed out, it's a shame those old fuddy duddies can't just let go! But you shouldn't let them spoil it for you!
Naruto: All right! Then I swear to become the great dirty old man in the world! Dattebayo!
Jiraiya: That's the spirit!
Jiraiya: OF COURSE I DO! To not do so would be an insult!
Naruto: What?
Jiraiya: Really Naruto, think about it! All these pretty girls are pretty for a reason. They put an enormous amount of effort into being pretty, by working out, training, taking care of their skin and hair, and dressing right! They WANT you to look, to appreciate them! To not look makes you look like a total coward, or that you have something on your mind other than them! It's an insult!
Naruto: Well... I guess... But-But it still wrong!
Jiraiya: Says who?
Naruto: ... Says... Says everybody!
Jiraiya: Well, not everybody is me. Did you know, all the best ninjas are dirty old men or women at heart?
Naruto: Really?
Jiraiya: Of course! You knew old Sarutobi! He was one of the dirtiest old men in the history of Konoha! And he lived well into his eighties for the simple reason that he didn't let those naysayers and killjoys prevent him from appreciating pretty girls! All this stress over not being able to look or compliment a girl can be killer!
Naruto: Seriously?
Jiraiya: Seriously! Look at me: I'm in my sixties but I'm no pushover! It is because I don't let the stress of some fuddy duddies too cowardly to appreciate the beauty around them get to me! I look and all are enriched by my looking because they know I have nothing to hide!
Naruto: Wait... Don't you?
Jiraiya: Yes, but as it usually doesn't concern them it doesn't make them worry, and that makes it easier to accomplish a mission when the people around you are not on their guard.
Naruto: Wow... Wait, what about Baa-chan?
Jiraiya: *smirks* Oh, don't let her fool you. She's tried to be a fuddy duddy herself, but she eyes the male eye candy just as often as I do the female-And even other females.
Naruto: *blush* S-Seriously?
Jiraiya: Seriously! Why do you think she has Shizune go around without underwear?
Naruto: What?! Nee-chan doesn't wear underwear?!
Jiraiya: Not the slightest bit of cloth between her nethers and the air.
Naruto: Woah... So... Orochimaru?
Jiraiya: HA! He tried to be a dirty old man but he could never quite manage! Got too locked up in immortality and binding shadows in the dark. *sighs* It is the saddest thing in the world when a man becomes so obsessed with not dying, or some other goal that he can't take a moment to look around and appreciate the beauty in every day life. If you stop doing it, you just start turning more and more to bad things.
Naruto: Oh man...
Jiraiya: Trust me Naruto, it's far better to be a dirty old man or woman at heart! Far less stressful, and far more honest! And as ninjas, honesty is at a premium. And with all the benefits, like making a girl feel special, making the people around you feel at ease, and making yourself less stressed out, it's a shame those old fuddy duddies can't just let go! But you shouldn't let them spoil it for you!
Naruto: All right! Then I swear to become the great dirty old man in the world! Dattebayo!
Jiraiya: That's the spirit!
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