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  • Anvilicious: The story really isn't shy about pushing the importance of honesty, considering how almost every conflict comes from characters lying or keeping secrets in a situation where they didn't have to.
  • Base-Breaking Character: While plenty of the cast can be divisive due to a few of the tropes below, Joro and Pansy are particularly standout examples.
    • People love Joro due to how he tries to invoke himself as a Manipulative Bastard who, unlike many other harem protagonists, is perfectly willing to call out the girls on their manipulative and selfish attitudes and his constant 4th wall breaks, with many comparing him to the likes of Kazuma and Hikigaya, who are also very well liked for similar reasons. Others, however, hate him for objectifying the girls, especially Pansy, and casually calling them bitches (at least in his mind). It doesn't help that in the later half of the series, his supposedly different personality compared to most harem protagonists starts resembling them, even when compared to a character that embodies the stereotype entirely.
    • Pansy is loved for her quick witted thinking and snarky humor, being Genre Savvy on many of the harem tropes that can potentially play out, and for being the first person to not only love Joro unconditionally, but also for sticking by his side after he gets ostracized by Sun-chan. Others, however, hate her for being manipulative to Joro and blackmailing him to spend time with her (a trait that she continues to use and is rarely called out for, though it is downplayed) and for being rather cryptic when it comes to what she wants from him, the most notable case being in the 4th novel with Hose.
  • Designated Villain: Invoked with Hose. While the atmosphere he gives off is suffocating due to everyone bending over backwards to let him fulfill his love life while he doesn't want to break his harem's hearts, the only real crime Hose himself has committed is being too agreeable and a bit of an orbiter. He's seemingly not aware of how his harem is trying to set him and Pansy up. Pansy admits he’s not really at fault for how things turned out, and him being too much of a designated villain to justify calling him out is part of the conflict. Then it’s subverted when it turns out that he’s a Bitch in Sheep's Clothing who’s fully aware of Cherry and Tsukimi’s crushes on him and that Pansy isn’t interested, but doesn’t care.
  • Ensemble Dark Horse: Despite being less prominent than the other girls, Sasanqua is considerably popular, owing to her being voiced by Shuka Saitō and her tsundere act being surprisingly endearing.
  • Fan Nickname: “Bench-kun” or “Darth Bench” for the Bench.
  • Hollywood Homely: Pansy’s disguised appearance really isn’t as wretched as Joro claims. To be fair, the only one who actually calls her ugly is Joro, who believes in the Buxom Beauty Standard and makes it clear that he has shallow taste in women’s appearances.
  • Ho Yay: A lot between Joro and Sun-chan. From the overtones of the Bench confession between them to The Reveal that Joro’s Shipper with an Agenda actions were really motivated by I Want My Beloved to Be Happy for him, it’s not hard to see Sun-chan as part of Joro’s harem. The Beach Episode plays it up for all it’s worth.
    • In the OVA, one of the girls in Sasanqua’s group gets heart eyes upon seeing Pansy’s hidden beauty.
  • Memetic Mutation: Bench-kun is the best anime villain of 2019.note 
  • Never Live It Down: A good chunk of the fanbase will never let Sun-chan forget the fact that he implied that he was going to rape Pansy no matter what. Some also think that he, Himawari, and Cosmos were all too Easily Forgiven for their actions in the first arc and think Joro shouldn’t even try to stay their friend.
  • Signature Scene: The part where Joro calls out Himawari and Cosmos for using him as a thankless wingman has left quite the impression on viewers.
  • Spiritual Antithesis: The fanbase is quick to see similarities with School Days, which has a very similar premise. The main difference is that the cast of Oresuki, who all start out as assholes with ulterior motives, become better people as the series goes on, whereas the cast of School Days appear moderately likable upon introduction before slowly becoming horrible dirtbags who will stoop to rape and murder.
  • Suspiciously Similar Song: The leitmotif for the Bench—simply titled “Bench” on the soundtrack—blatantly rips off cues from the Imperial March.
  • They Changed It, Now It Sucks!: Some fans who were drawn in by the ruthless Take That! on the harem genre in the first arc consider the subsequent arcs’ Satire and Switch to be a disappointment, feeling that Joro taking a level in kindness and having girls besides Pansy actually attracted to him takes away what made the initial premise so unique.
  • Too Bleak, Stopped Caring: The first three episode arc really hammers in the Dysfunction Junction perpetuated by a World of Jerkass, which some found too off-putting to enjoy even when it’s played for Black Comedy. Later arcs dial it down on the cynicism and have more genuine heartwarming moments to lighten things up, but there’s still a lot of twisted nastiness in the first arc to get through before that point is reached.
  • Unintentionally Unsympathetic: Cherry and Tsukimi's unrequited crushes on Hose are meant to make the reader pity them and show how he unintentionally makes the lives of everyone around him miserable. However, it's really hard to feel much sympathy for the girls considering how their hell is entirely self-inflicted and they'd rather whine and wallow in their misery out of fear of being rejected instead of being honest with their feelings and confessing.
  • Why Would Anyone Take Him Back?: For a certain portion of the audience, Himawari, Cosmos, and Sun-chan’s actions in the first arc were too heinous and too Easily Forgiven for Joro to even want to be their friend anymore, much less want the girls in his harem.

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