 If you liked
Gabriel DropOut
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 ...then you might like
Fantasy Bishoujo Juniku Ojisan to
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Not only does the main character Gabriel and Tachibana from each anime look extremely similar, the side characters also have a similar vibe to them depending on their intelligence and knowledge level. Although two completely different plots, the characters appear almost the same in each anime.
By watching these two, it is almost like looking at a mirror at how the characters would continue to play out the story line due to their similar nature and both feature good character development for their characters. Thus, if you like one, you should also like the other.
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