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Originally Posted by Dareal_truth
Possibly but again they have ExE underway wouldn't it make sense to do it in a time skip scenario?
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No multi-year timeskip will happen since Ishibumi doesn't want that. Because technically, it stops being High School DxD [Devil x Dragon] if Issei is no longer a highschool student.
Doesn't make sense to do a timeskip right now with the alien invasion reaching full swing. Such a timeskip would have been better right after the Evil Dragon War.