Why is it the best canon romances are the doomed ones?

Because then the writer tries harder? Because sad is easier to write well than happy? Beats me.

That's true. But you don't say it. I know it's Jiraiya and he would, but then again, he never gets the girl, so his being blunt is a bit of a give and take.

*nods* Honestly, though, Tsunade had him in so clearly 'not an option' catagory, that... well, he needed to make a move sometime after she came back to Konoha. That might've worked.