Jiraiya kniws naruto but not really in his family no.
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not sure yet..... sorrily...........):
25
yes,in episode 168 of shippuden
I may be possible. Why? Because Masashi Kishimoto, the creator of Naruto, based Jiraiya, Tsunade, and Orochimaru off of a tale called The Tale of the Gallant Jiraiya. In that tale, the character Jiraiya is married to a woman called Tsunade. Orochimaru is Jiraiya's enemy, and attacks the couple. So, it may be possible that Jiraiya and Tsunade like each other in a maritial way.
yes