Ok, this is my guess for matchups for the possible end of it all. And yeah, there is things more to naruto then just fighting, theres alot of character development and would tie into this:

Naruto - Hinata (might be awhile before hinata opens up, but you can see it)
Sasuke - Sakura (once sasuke comes back (if?) from oro/itachi issues)
Shika - Ino (shika knows shes troublesome and all, but thats how those kind of things start)
Asuma - Kurenai (Dunno bout this one, kind of a guess, but they seem pretty close)
Tsunade - Jiraiya???? (Only pair i think could accually work with her, but its doubtful)

Any others im missing/wrong on?