No. Absolutely not. I love same-sex pairings, but this is one of those that could never work in a million years.
Yes, they were best friends at two points in time, but throughout their teenage years and much into their adulthood, Obito regarded Kakashi as an enemy whereas the latter believed that Obito had been dead for nearly twenty years.
Kakashi was blamed by Obito for so many wrong-doings, but he held the bitterest grudge towards him in terms of their teammate Rin's accidental death. Obito was unaware for many years that Rin sacrificed herself to protect the village and her friends in case anyone came after her to steal the three-tails while Obito believed she had been killed in cold blood.
It was very much a repeat of Sasuke and Itachi, and on top of all of this bad blood between them, a romantic relationship would never work out. No hate towards any who likes this ship, but that's just how I feel about it.
Overall, 3/10 (points for some mild cuteness)
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Rating Naruto Ships
De TodoSend in a Naruto ship, whether it be cannon or not, and I'll give you my honest opinion of it.
