If you liked
Otome Game no Hametsu Flag shika Nai Akuyaku Reijou ni Tensei shiteshimatta...
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...then you might like
Ore no Shibou Flag ga Todomaru Tokoro wo Shiranai
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I would say these are similar. I would say they are, but if I had to state something they aren't similar in is how Hamehura did it better. I won't get into detail but Ore no Shibou Flag follows a male protagonist while Hamehura follows a female one. They have around the same setting, but with a different cast and major events. I think Ore no Shibou Flag has a good concept, but something went wrong in production *cough* where's the introduction *cough* it was only one speach bubble long *cough*. But if you happened to like it maybe Hamehura will pique your interest. I'm personally not the biggest fan of this villain/villainess fad but to whoever you are I hope you like a school setting, because for some reason Harold (or at least that's what I think his name is, MAL doesn't have a profile for the Ore no Death Flag MC while I'm writing this) doesn't need it. Happy reading :P
If you liked
Kagerou Daze
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...then you might like
Shuuen no Shiori
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I'm not sure actually. It's gives the same vibe, and in general the art looks similar. They both have this "mystery" attached to them.
If you liked
Bungou Stray Dogs
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...then you might like
Sugar Dog
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Both have organizations that can defend themselves and defeat their enemies. They have a chaotic but cool atmosphere. Their charm basically.
If you liked
Fate/stay night: Unlimited Blade Works
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...then you might like
Lostorage Incited WIXOSS
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Holy Grail War Styled Theme minus the trading cards for one and the magic (mostly) for the other
If you liked
Rokudenashi Majutsu Koushi to Akashic Records
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...then you might like
Maou Gakuin no Futekigousha: Shijou Saikyou no Maou no Shiso, Tensei shite Shison-tachi no Gakkou e Kayou
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Both series carry a likeable cast and give the option to either take seriously or not. Both are packed with laugh (you could say that) moments and have good character designs. I go back and look at them sometimes, though the series' ended a while ago.
If you liked
Rokudenashi Majutsu Koushi to Akashic Records
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...then you might like
Arifureta Shokugyou de Sekai Saikyou
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I think the main similarity is the fact that they're stories give you an option to take it seriously or to simply not. They both do a pretty good job regarding character likeability and designs but Arifureta is behind on backstories. Neither MC has gone all out on screen, so I guess we could say they are similar in that way. Both are a good watch, depending if you can handle some ecchi and strange writing choices. I'd say the writing choices are good if you enjoy drags (sometimes) and character interactions.