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Ookami-san to Shichinin no Nakama-tachi

Synopsis:

Have a problem? Talk to Otogi Bank, a student aid group that helps people get what they need – for a hefty price. Led by Liszt Kiriki and staffed by tsundere Ryouko, inventor Majolica, jealous Otohime, flirtatious Tarou, serious Alice, nervous Ryoushi and maid Otsuu, Otogi Bank assists with everything from helping break into a rival school to convincing an upperclassman to not quit a sports team. Can Otogi Bank manage to make all their clients happy, and most importantly, will Ryoushi ever manage to win Ryouko’s heart?

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Working!!

Working!!

Self-professed lover of all things small and cute, Souta Takanashi finds himself dragooned into working at the Wagnaria family restaurant by the diminutive and vivacious Poplar Taneshima. Though the pay is reasonable and the clientele polite, the high school student is often at his wits' end when dealing with the quirky staff. If the indifferent and street-tough manager, katana-carrying floor chief, and terminally weak Poplar weren't enough, Souta frequently fears for his life, as every encounter with the violently androphobic Inami ends in injury. How long can he survive before the combined stress and harm do him in?

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sobeit

Both include a character which try to overcome their psycholigical issues for the person they like

Zero no Tsukaima

Zero no Tsukaima

In a world where magic is a reality, the young Louise is at the bottom of her class. Dubbed "Zero" by her classmates at Tristein Academy (due to her zero success rate for magic), Louise (along with all first year students) was charged with summoning a familiar; and instead of a cute magical creature, the familiar arrived in the form of... Saito Hiraga, a normal Japanese boy who was abruptly teleported from his own world?! Can both Louise and Saito come to terms with their new and complicated "relationship" and (more importantly) help Saito find a way home?

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Kryn

Both these anime have the same kind of day & age feeling, as if they're both made in the same generation. The main protagonist in both anime are tsundere and are generally vicious towards the main male, although there are slight differences in the way they act, such as Ookami-san showing more appreciation towards the male than Louise. If you liked one you'll like the other, mmkay?.