The fact that when people think about “the next generation surpassing the previous one”, they immediately relate it to a nice guy getting into the pants of a girl who isn’t romantically interested in him is kinda scary. I mean:
“Obito should have gotten Rin!” Rin loved Kakashi and while she treasured Obito as a dear friend, there was no implication she loved him romantically.
“It’s so sad! Jiraiya loved Tsunade until he died!” You know what’s truly sad? The fact that you forgot Tsunade had her own love who died and she still loves him long after his death. No one spares a thought for Tsunade, it’s all about poor Jiraiya and his poor, poor unrequited twu wuv.
“It’s so sad that Naruto didn’t surpass his predecessors and get the girl!” Because that was totally his goal at the beginning of the manga. I vaguely seem to recall it as something that has to do with becoming Hokage and being acknowledged… Both of which he achieved.
Let me tell you something: Just because a guy is nice to a girl, doesn’t mean she owes him her love. Being nice to someone else is called being a decent human being. Being nice to someone is not okay when it’s only used as a ploy to get into someone’s pants.