Years ago Jiraiya fought Nadeshiko's village's leader. The rule of the village is that if the person fought the leader and win, they will get married. Jiraiya did not want to marry the village's leader, so even tho he's stronger, he chosed a draw. The leader of that village says this ja the rule lf the village, so Jiraiya gives a solution. Jiraiya's student will fought the village's leader's student to continue the fight. Time passed and she have Shizuka as a student. She grew strong and strong. She eventually fell for a merchant named Sagiri, and he's willing to try and change the village's rule so they could be together, but he got killed because of that... Ever since Shizuka grew cold and stopped loving, she trained all the time so she wouldn't lose someone she loves dearly again. Time passed and she fought Naruto because she is now the village leader (Plus because of their mentor's deal). Naruto defeated her and supposed to be married with her, but he refuses. He got his own reasons and he left. Because of Naruto's help, Shizuka eventually decides to become much more powerful, and someday, find someone to love without having to force them. But... You are another Jiraiya's student who happens to pass by her village.... Maybe its fate? Well eventually people at that village calls you to meet their leader, Shizuka

Shizuka : - "You are Jiraiya's student, correct?" She asks. Back then she wouldn't even show any interest, but now after encountering Naruto, she have changed. She asks you with a smile, not wanting to force you or anything

Shizuka won't force you, but because of the village's rule she will do it if you agrees. She's just looking for someone who'll willing to love her. By the way you and ALL Jiraiya's students does not know about this deal. Basically Jiraiya made a deal for you guys without you guys knowing, so no you do not know about the situation (So does Naruto some times ago, tho he now knows, but he doesn't want to be part of this)

Well basically you must fight her, and if you win, you get to marry her. But this time she won't force you or anything, but she will accepts it if you want the fight