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We know what Lucanis thinks about the abuse he endured at the hands of Caterina, that it was necessary for his survival as a Crow. What do you think Illario feels about the "training" he received? Would he agree with Lucanis?
Illario and Lucanis went through the same abuse during their childhood. They were beaten and starved. It was Caterina's terrible way to train them to become perfect Crows. According to the Wigmaker Job Lucanis actually resented Caterina for years, before he succumbed to the "but this was necessary" mindset.
I imagine Illario would consider this necessary and normal just like Lucanis did, but deep down he still hates Caterina. Combined with being the non-favorite Crow, he never had a good relationship with her. He considered the training normal because he never received love or a normal childhood. He doesn't really have anything to compare his experiences to. He was surrounded by other Crows. So this is why to me it feels like his hatred towards Caterina comes from her liking Lucanis more. Maybe because of this he thinks all the things he went through when he was younger were for nothing. I always felt like Caterina succeeded making Illario into the "Crowy Crow" and when started acting like that, she didn't want it.
He didn't have any role models other than Caterina, so if it wasn't for Marcus, he would have probably become Caterina 2.0. when it comes to their own children.
Here are some questions and suggestions for the Day 4 prompt Hunger/Sustenance.
What was it like when Caterina withheld food from him? How did he cope?
What does Illario crave the most in life?
What kind of support does Illario need?
I headcanon that both Illario and Lucanis still have some eating disorders, still lingering as a consequence of being starved during their training. Illario loves to eat, he loves good food, but the other reason he eats so much is to make sure he never goes hungry again. But he also doesn't want to appear not-perfect so he takes care of his body. But as a child, he ate any crumbs he could get. I can imagine since Caterina's was goal to make the cousins as emotionless as possible, she might have introduced a cute pet to them. And when they formed an attachment she switched on the Starve days and made them hunt the pet down. That was their dinner. It must have been terrible to go hungry at night when he was a child. No food, no water for days. But he got used to it. He had to. Didn't have any other choice.
I feel like saying "he craves love <3" and "he wants POWAH and be a big bad First Talon" are both kind of....shallow and oversimplified? Because everything is the consequence of something. Caterina didn't favor him at all, he was never a first choice. So Illario always wanted to feel accepted, acknowledged and the best way to do that is if he becomes First Talon, that's like the final prize. But I also headcanon that behind him being this extrovert, social and flirty person he knew that the people who wanted to sleep with him wanted to sleep with the Crow, or the Dellamorte, not Illario. No one really wanted to get to know him. He didn't want to get to know anyone either. This was his routine. He accepted that this is the furthest he will go as the first choice in his private life. I do feel like Illario likes being a Crow, and him wanting to become First Talon is a natural process, but it's rooted in him being the ignored grandson. In my worldstates he becomes First Talon and that's something that he wanted and was good at it. But he didn't know how much he needed to find someone that really loves him, and for whom he is the first choice. The only choice.
If it was a modern world Illario would really need a good psychologist as support. But his partner is a good choice B.
"Your hair is getting grey already? Why?" Marcus: I don't know....
Meanwhile Illario with the kids:
I still wonder if Illario got creative and pulled a Hannibal on Grandkid One. Not the cannibalism part, just the creative murder method.

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Illario Week: Day 4 - Sustenance
Illario enjoying a plate of cacio e pepe at the Villa. I think he'd be so happy to be home after a contract gone awry and experiencing what passes for pasta in Tevinter.
Just thought I'd do something cute for today and for @paxvoik2 since this is something she wanted to see. :D This uses the Loumon base.
Art of Illario eating is another dream come true for me. I think he is not used to people cooking for him, people who are not doing it because it's their job. In my headcanon Illario can cook, he is average. he can make recipes he likes, but he would rather just jump to the eating stage. It's more fun to him than making the food.
I love characters who are like "I'm a terrible person" but when you look closer it's more like
"I adapted to survive something and now I don't know how to stop being that version of myself."
Illario Week 2026 Day 5
Thank you for the game @illarioappreciation and @lustaniasaxon 💜🫂
Day 5 Prompt
Week Prompt List
Chaos/Conformity
"Dellamorte the Lesser", "listens only to himself", "that idiot". Say what you want but Illario is cunning, proud, ambitions and capable of anything to achieve his goal, never afraid to make his hands bloody. For the sake of the coveted title, he is even ready to sacrifice his family.
Just as current First Talon herself.
It looks like you managed to raise true Crow of him, Caterina.
Aren't you proud of yourself?
Illario Week 2026 — Conformity
Day 1 ✦ Day 2 ✦ Day 3 ✦ Day 4 ✦ Day 5 ✦ Day 6 ✦ Day 7
"Chaos/Conformity" for Day 5 of @illarioappreciation
Bound to love chaos in a world of forced conformity. A Dellamorte never kneels. A Dellamorte never bends. Stand straight, show composure. Repeat it like a mantra. Prove your worth. One for silence. Two for surprise. Three for good measure. Four's exercise. Five for a slaughter. Six for the thrill Seven means more sovereigns. Eight marks the final kill.
Sketch & thumbnail doodle

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Marcus: You are so demonic even without being possessed, that's quite the achievement. Absolutely terrible. Maybe you have a split personality and you are talking to yourself in secret.
Illario: Is that what you think? Maybe we should get Varric's opinion, which corner is he standing at?
Marcus: Oh fuck off!
Marcus likes to have some private time to himself, resting peacefully in a quiet corner on the estate. Alone. This is why he got himself a hammock in the garden. I had a scenario in my head where he was napping in the hammock, it was so quiet and cozy. But then suddenly he felt the hammock sink lower and lower. When he opened his eyes Illario was already half way in the hammock. Marcus told him it can't hold his heavy ass and the space is too small for the both of them, but Illario didn't care. He must participate in Marcus's activities, he needs to be there. Even when there is absolutely no reason for it.
Illario would tell Marcus it's not his fault, he must have attached it wrong to the trees and that's why the hammock collapsed. 👺
Probably the most out-of-place post I'll ever make, but I'm currently watching The Expanse (it's sooooo good, omg), and one of the characters suddenly starts wearing a man bun, and ever since then, my brain has been physically incapable of not going, "OMG, ILLARIO DELLAMORTE????" every time he's on screen.
I mean, look at him:
THAT'S HIM!!!! Or I'm going crazy.
Am I going crazy?

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Lucanis and Illario through time for @datvcompanionweeks Lucanis Week Day 6: Past | Future
I drew this Lucanis and Illario through time one year ago and always thought I should do a happier one with a post-game version of them!
Oh, I adore this interpretation of the prompt! I love the progression of Lucanis and Illario as young boys into adulthood. The colors are so fun and fresh and the art style is adorable! Thank you so much for sharing!