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SFW Reader-Insert Headcanon Scenarios ; Octavinelle
Summary:
An updating collection of all the headcanon-format posts I’ve made that involve one or several of the characters from Octavinelle being paired with a reader insert character.
Unless explicitly stated in the title of a chapter, please assume that the reader insert is gender neutral.
Tags and pairings will be updated as necessary to account for new requests.
The lowercase text is intentional.
Chapter 1: what it’s like to date azul ashengrotto
Summary:
originally posted in march 2026.
Chapter Text
- azul ashengrotto: aspiring entrepreneur, manager of a thriving business, former head of an underground study guide trading ring, a true businessman in the making if ever there was one. a man so charismatic and manipulative that he could probably sell ice to snowmen and still manage to turn a sizeable profit. one would assume that such a character would enter a romantic relationship with nothing short of complete and utter confidence, but alas when azul is with you its like he becomes a completely different person — or, rather, that he drops the act and shows you the sides of himself he was previously too terrified to acknowledge or accept (much to the unending amusement of the leech twins who have seemingly made it their collective life mission to never let him live down how soft you’ve made him… but they will be dealt with in due time…)
- he tries so so very hard to be the perfect boyfriend for you — studies every dating advice column and online guide and romance novel he can get his tentacles on, spends hours in front of the mirror in his dorm room practicing his smile to make sure its just right, devotes his free time (between shifts and studying and classes and club time) to planning out the perfect dates for you both, and so on — and he looks so proud of himself whenever he nails an expression or flirty remark or romantic gesture that you usually just let him get away with it. but inevitably the pressure will get to him and he’ll end up stressing himself out so much he’ll end up messing up and retreating into his octopot out of shame… so… be sure to let him know that you want him as he is, not for who he thinks he has to be for you, before he goes prematurely grey and has a breakdown… please
- it doesn’t matter if you’re the love of his life, he will keep on trying to get you to sign contracts with him. the only real difference is that the contracts he offers you are far more lenient and forgiving than those he offers to the other poor unfortunate souls at night raven college — and the price he asks for is pretty much always either something to do with affection (e.g. x amount of kisses for him to help you study for this exam, you staying overnight at his dorm for the whole weekend if he lends you his class notes, etc.) or something more symbolic and cute (e.g. signing this contract means that azul will have sole ownership over your heart for the rest of your days, or some other such thing), though the latter is never used as a payment for actual contracts and is more so something he’ll tag onto the end of a verbal agreement to make you smile
- when it comes to the things you tell him about yourself, or that he learns on his own just by being around you and those you’re close to so often, azul makes an effort to commit everything to memory. after all, you’re the person he intends to spend the rest of his life with and he wants to put his best foot (tentacle?) forward with you every step of the way — and if that means meticulously cataloguing everything from the big things (like allergies, preferred fabrics, favourite foods) to the most minute details about your person (like what mood that specific scrunching up of your nose corresponds to) in enough notebooks to fill a modestly sized bookshelf to make sure he always knows how to take care of you in ways that you’re sure to appreciate, then so be it… besides, its not like he’ll ever be short on ink to write with
- no matter how much he adores you and trusts you (which is a great deal), azul’s insecurities have plagued him for most of his life and his fears are not going to suddenly vanish overnight now that he has a loving and supportive partner. all that to say, it will take a long while before he feels comfortable even just discussing letting you see him in his octomer form, and longer still before he can work up the courage to actually show himself to you. just know that its nothing to do with you, not really, and he knows that you won’t hurt or belittle him… its just that he can’t help but be terrified of disgusting or scaring you off after being treated as poorly as he was during his formative years. just be patient with him and let him go at his own pace, okay?
- he has an awful jealous streak, and while he will never lash out at you or make a scene around others (as he has a certain image to uphold as the manager of the mostro lounge and as a housewarden), he will use every underhanded method at his disposal (blackmail included) to make the person who he’s jealous of have an absolutely horrible time until they back off on their own or sign a contract to better their circumstances that comes at the cost of distancing themselves from you. though he will only go to such extremes if that person is actually flirting with you or coming close enough to doing so for him to get upset about it — he’s jealous, not irrational
- a lot of your dates will take place at the lounge — its where he feels the most comfortable, its where he is in complete control, and its somewhere that he can guarentee you’ll always receive the best quality service anyone can provide, so its the most logical choice. but if there’s another cafe you want to visit with him, or if you want to go on a date that’s a bit more active than just dinner and conversation, he’s always up for suggestions… just give him some heads up so he can plan ahead as needed
- having such a keen sense of taste means that all azul needs is a decent sample of any particular food items or drinks that you’re especially fond of to be able to note down their ingredients and, down the line after some experimentation and troubleshooting, recreate them for your enjoyment. all for the measly price of your undivided attention and some kisses, of course
- if you ever find yourself in hot water with another student, or most anyone else on sage island or in the coral sea for that matter, he’s more than happy to send one of the leech twins to help settle the matter on your behalf. and whether its jade or floyd who pays the other party a visit you can bet that you won’t be dealing with them ever again
- do not ask for his help for any sort of physical activity, not unless you want him to send the twins on his behalf or collapse a shameful number of seconds into the activity at hand, completely and utterly exhausted and dearly wishing for the floor to open up and swallow him whole. academic stuff is his strong suit, not physical education… for both of your sakes do try to remember that
- he knows all too well how eager his family are to meet you because they ask about you near-constantly whenever he makes the journey back home to the coral sea. his mother and step father both are happy that he seems to have found his person the first time around, and his grandmother is delighted by how much more confident and happy he’s become since the two of you became an item. needless to say, when you finally make the journey down you will be getting the warmest welcome a family of mers can offer and you will be spoiled rotten — just make sure to clear your plates!
- this is more of a general octomer thing than an azul-specific thing, but he is exceptionally tactile — especially in private, even more so when he’s sleeping, and even more so when he’s relaxed in his mer-form. his grip is tight and unyielding but not uncomfortable or suffocating, his head is usually pressed into your neck or resting on your chest/stomach, and its the most at ease you’ll ever see him. bonus points if you hold him back just as tightly as it scratches a certain itch he didn’t realise he had before you — but please never bring up his clinginess in front of the twins because they will never let him live it down
- with how much work he puts in to making his own looks appear entirely natural to the eye, its easy to forget just how much azul knows about skincare and makeup — which is by design, of course. but if you, as his partner, ever came to him seeking insight about how to improve your own routines or about how to find a product and shade and style that works for you, he’d be more than happy to offer his services
- not counting the lips, his favourite places to kiss you are on your hands (specifically your knuckles, fingertips, and the insides of your wrists) and your cheeks, and his favourite places to be kissed are over his beauty mark and his palms
- his default pet name for you is ‘my pearl’, but he is also quite partial to some more land dweller leaning terms of endearment like ‘sweetheart’ or ‘darling’ or ‘my dear’, and will use them every now and again when the mood strikes him
- this man is stubborn enough to try and meticulously train the chance out of a game of chance after losing to idia at it once, but he’s willing to set aside his pride and stubbornness if it means earning your approval or making you happy. it’s not easy for him by any stretch of the imagination, mind you, but you’re well worth it in his eyes so the occasional minor blow to his pride is negligible
- if you asked to join in a session at board game club azul would both welcome you with open arms and jump at the chance to show off for you by either teaching you how to play a specific strategy game and presenting himself as the paragon of patience and good teaching, or by challenging his fellow club members to games that he knows he’s going to win and absolutely destroying them in order to earn your praise for his skills as a strategist and player (which idia will 100% mock him for under his breath because it is so painfully obvious to him how whipped the octomer is for you that it borders on comical… cringe too, for sure, but comical nonetheless).
- he’s just as uncompromising when it comes to selecting the best and most personal gifts for you as he is when it comes to stocking up the mostro lounge with the best tablewear he can afford. after all, he knows that he doesn’t have to worry about being in debt to you because you’re his partner (contrary to what his finely honed business instincts may try to tell him whenever he goes out shopping for you), and as a result he truly spares no expense if it means making you smile
- you’re his first partner and while he does try to cover his inexperience through research and adapting to the things he observes that you like during your time together, there’s really no hiding how nervous he gets once you really know him. and, as such, he does try and take on your advice and assurances and requests whenever you make them to be able to properly reflect and better himself as your boyfriend… even if it does hurt his pride a bit whenever you (gently) call him out for overcompensating or being performative with you
- this is especially true if you’re a land dweller, but azul frets so very much whenever you’re unwell. his usual overpreparedness gives way to intense negative spirals of thought as he goes into overdrive trying to figure out what’s wrong and what he can do to help… which involves doing his own research, coming across something awful that kind of fits the symptoms you’re showing, and then convincing himself that you’re on death’s door and it’s all his fault for not properly accounting for how fragile land dwellers can be. it’s not fun for him to experience and it’s stressful for you to watch him spiral so much, but thankfully for both of you he does get better about rationalising his way out of these negative spirals the longer you’re together (he never stops fussing over you though, he’s just not catastrophising about your illness while he does it)
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