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Illarook Week 2026

Summary:

What if Isabella fell in love Illario instead of keeping their relationship platonic and professional? We're gonna explore that here!

Day 1 - First
Day 2 - Jealousy/Envy
Day 3 - Date Night
Day 4 - Conflict/Regret
Day 5 - Whispers/Secrets
Day 6 - Forgiveness/Comfort
Day 7 - Past/Present/Future

Chapter 1: The First of Firsts

Summary:

Day 1 - First

Several years before Veilguard, Isabella has a contract that will make her a full Crow. However, when the person who was supposed to supervise the contract falls ill, Illario volunteers to impress his date at the time.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Isabella exhaled softly as she did her best to calm her nerves. This was going to be the contract that was going to let her join the Crows. She had been training for years for it, proving herself over and over to Viago to show that she was ready. Viago even spent weeks searching for the appropriate contract for her to have a perfect balance to showcase her skills and hard work.

Viago nearly had a coronary when the Crow didn’t show at the Diamond that was supposed to guide her through it. The Crow contracted the stomach flu overnight.

Most, like Isabella, would have called it bad luck.

Viago said that it was the gods laughing at him.

Illario often called it Fate.

Isabella expected the contract to be called off for a more experienced Crow to handle it only for another Crow from an entirely different House to step in. The surprise silenced the room as Illario Dellamorte stepped forward to offer his services instead. Isabella half expected her brother’s head to explode from the quiet fury he possessed. 

Illario had stepped forward to impress another pretty Crow from a lesser House who dared him to speak up. They had been spending the day at the Diamond, and the little display happened not too far from where they were drinking. He had expected Illario to turn him down, and he could start the breakup process. Instead, Illario valiantly stepped forward to play the hero of the hour. 

Without another option that didn’t involve another month of planning and rearranging, Viago accepted Illario to substitute for the absent Crow. Isabella clenched her jaw, knowing that this was her best chance of becoming a Crow. She also knew that her job just got a whole lot harder than before. 

She had heard rumors of the younger Dellamorte and while he got his contracts done, he wasn’t as dedicated as he should have been to them. So, when she heard that he had stepped in to impress a pretty Crow who dumped him later that day, she had to go find him. She expected that he would be at the Dellamorte villa, but she ran into him in the streets, passed out from drinking and staying out late. He had stayed in the nicer part of town and tucked himself away in an abandoned alleyway away from prying eyes. 

Isabella practically dragged him into the nearby cafe where she bought him a coffee and waited for him to wake up. His hangover had been a nasty one, but she wasn’t about to let him ruin her best chance of becoming a full Crow. Not when she was this close. She was already too old to be a Fledgling. Viago didn’t want her in the line of duty before he was sure that she was prepared fully. Still, she felt like being in her mid to late twenties was too old to still be a Fledgling. 

That had been a few days ago, and now they were well on their way to Seleny for her assassination contract. Illario had offered to hire horses or a carriage for them, but she refused. They needed as much stealth as they could muster for this deal, which meant that they were going to be walking there. Which meant it was going to be a difference of a week instead of two to three days to get there, and that was if Illario kept her pace. It would take longer if they slowed down, which meant that Isabella was constantly on him during the journey.

They were about two days outside the city when the sun was starting to set again. Isabella wandered off the path to make sure that they could camp in a more secluded place away from bandits and opportunists. She started to roll out her bedroll from her pack as Illario started a fire, as usual. While the light was visible from the road, it was far enough away to be an easy target. 

“Two more days until we reach the city,” Isabella mentioned with a sigh, sitting on the fabric she set out. Illario smirked, glancing up at her. 

“Then we should get our story straight,” he commented as she raised a brow at him. 

“Our story? We’re supposed to be blending in the with the shadows, not playacting through a story,” she reminded with a scoff. Illario chuckled as the fire burned bright. He leaned back on his heels before smiling at her with a roguish charm. Isabella narrowed her eyes at him, getting the feeling that he was teasing her. 

“That was when you were with a stealth expert and a de Riva Crow. You are now with a seductionist and a Dellamorte, and I don’t blend well with the shadows,” he informed plainly. She clenched her jaw, realizing that he was still going to be difficult about this. 

“Unfortunately, stealth is still one of my strong points, and I am still a de Riva Crow. You should have known what you were signing up for before you volunteered,” Isabella remarked almost bitterly. Illario chuckled, moving to sit more comfortably with one of his knees bent to let him rest his arm in the air. 

“And Viago should have told you that sometimes you need to be flexible when plans change,” he countered. Isabella exhaled in a huff, irritated that he was correct. She needed to learn to be able to be flexible when plans changed, otherwise she could find herself in a dangerous situation with no way to think creatively. 

“Fine,” she relented, folding her arms. “What did you have in mind? Did you want to infiltrate while acting as a nobleman or something? I doubt your pride would let you be anything less.”

“Something like that,” Illario admitted, ignoring her jab about his pride. “I was thinking you and I could pose as a married couple touring the city, and we can enter the lord’s good graces. When he has his guard down, you simply strike, and we sneak out like nothing ever happened.”

“You want to pose as a married couple?” 

“It’s the most innocuous way to travel together and gather intel.”

Isabella could barely believe what she was hearing. She had met the man a week before, and now he was suggesting this. Isabella scoffed under her breath as she shook her head.

“We barely know each other,” she pointed out, gesturing at the distance between them. Illario shrugged, leaning forward with a seductive smirk. 

“It seems like a wonderful time to start, don’t you think?” he suggested. Isabella stared at him, realizing that he wasn’t teasing her. He was serious. He seriously wanted to do it this way. “We could ask each other questions, yes? I could start. I enjoy drinking wine to unwind after a contract or after a long day. Do you drink?”

“I don’t drink unless a contract asks me to,” Isabella commented, glancing to the side. Illario noted a pink tinge to her cheeks, finding it rather interesting. 

“So, you don’t drink for fun?”

“No, I don’t. I... don’t like to lose control.”

“Ah,” Illario whispered, his tone a little softer. It was almost more comforting than she expected. “Then I don’t think it will be required on this contract.”

“You don’t know that. We haven’t even scoped the place out yet,” Isabella pointed out before he shrugged.

“Then I will do the drinking,” he answered. Isabella blinked at him in surprise before he leaned back and propped up himself on his arms. He sat in thought for a moment. “Let’s try a better question to start... ah, what is your favorite food, mi querida (my dear).”

Querida (Dear)?” She chuckled before he smirked.

“That is not a dish I’m familiar with,” Illario teased, earning a laugh from her. She smiled softly despite herself. 

“Cacio e pepe. I like more western Antivan dishes,” Isabella answered honestly. Illario sat up again, his seductive smile turning into something sweeter and more genuine. “What about you? What is your favorite food?”

“No term of endearment for me, cariño (sweetheart)?”

“We aren’t married yet. Ari,” she teased with a playful tone. Illario blinked at her, not hearing that nickname in a long, long time. It stirred something deep in his heart that he thought was long gone by now. “So, tell me your favorite food.”

“Fideuà with shrimp,” Illario answered with an appreciative hum. He wished he had some now rather than the dried meat and fruit that they had brought along with them. Maybe they could find something similar in Seleny. Although, they were more likely to find cacio e pepe than fideuà out there. 

“I do love seafood,” Isabella nodded with a chuckle. “I don’t know what other questions to ask. I guess what do you like to drink other than wine?”

“Well, coffee is always nice,” Illario replied, thinking back to when he woke up a few mornings ago in a strange cafe with an angry Fledgling in his face. Isabella smirked as she nodded. “But I think I would have to say a nice lemonade with a hint of strawberry and lime.”

“That does sound very refreshing,” Isabella agreed. “I think mine is coffee with a bit of sugar added. I’m not opposed to cream if the taste is super bitter.”

“I should have known when I woke up in the cafe,” he teased.

“I’ve heard black coffee is a great hangover helper,” she argued. Illario laughed gently as he stared at her for a second. Even though she was angry with him, she got him something that could have helped him. Strange, especially for a de Riva. A good strange, though. 

“What did you mean you don’t know what questions to ask, though?” he wondered, realizing that he had only really asked two to her. Isabella lifted her shoulders. “Am I not intriguing? Do you not want to know more about me?”

“I suppose, but I’m not sure what to ask,” Isabella answered honestly. “What questions would you ask me? You seem to already have an arsenal of prompts in your head.”

“Not sure what to ask?” he pressed before moving closer to her. Isabella threw her walls up nearly immediately as he looked at her. “You could ask me anything, and I would give you an honest answer.”

“That doesn’t mean I would know what to ask you.”

“Well, we are kind of treating this like a first date, aren’t we? What kind of questions would you ask on a first date?”

Isabella turned her head to the side as it burned red in the firelight. Illario thinned his lips, realizing that he had pressed too far, even if he didn’t realize he was heading towards a line. He leaned back again, hoping to give her some space. 

If this was to be her very first first date, then he would at least make it memorable. Even if it was for a contract, it would make good practice for the future. He thought to himself for a moment before thinking again. 

“If you were to go anywhere in the world, where would you go?” Illario asked, startling her. Isabella turned towards him with her brows furrowed.

“What?”

“If you could go anywhere, where would you go?”

“I... I’m not sure,” Isabella replied as if the question was strange. Illario tilted his head, wondering what went on in that head of hers. “I suppose I’ve always thought Rivain would be an interesting place to go to.”

“Anywhere in Rivain?” he wondered, pressing her.

“To the cliffs along the coast. Or maybe along the beaches? Somewhere nice and warm,” Isabella thought as she stared into the fire. Illario really looked at her as she was lost in thought.

There was a vulnerability in her eyes that he never saw in any de Riva. He watched her as her mind likely danced with the idea of going to the beaches and playing in the water and sand. Illario found that he wanted to give her that, even after all the issues along the road they had so far. 

This had actually been the first conversation that hadn’t gone up in flames with her angry, irritated, or exasperated with him. He found it... almost addictive. That look in her eyes gave him a sense that he was getting through to the real person behind the walls she constantly held up, and he wanted to know that person. 

“What about you? Where would you go?” she wondered, looking at him now. Illario met her gaze, surprised to see that the walls were still down. Her eyes were curious rather than skeptical for the first time he had known her. 

“I was going to say Orlais or something, but I think Rivain sounds much more fun,” he sighed as she hummed, tucking her knees under chin as she wrapped her arms around her legs. 

“Have you been to Orlais or Rivain before?” 

“Only Orlais, but I’ve seen paintings of Rivain. I’ve been to Tevinter more often, and it’s better to stay in Antiva over Tevinter.”

“I hear a lot of contracts go out that way,” Isabella mentioned. Illario shrugged and smirked.

“It’s the only reason to go there, in my opinion. It has its own rich history, but the Venatori made a mess out there. It’s good for business, but bad for tourism,” Illario answered as she listened intently. It seemed that she didn’t hear much about the ins and outs outside of Antiva. “Where have you been?”

“I go down to Salle once in a while with Viago when he needs to deal with de Riva business,” she answered quickly. Honestly. “Most of my life has been spent in Treviso. It was one of the reasons I was excited to get to Seleny.”

“I suppose we’re not that different. I was born and raised there as well,” he commented as she chuckled, glancing to the side.

“We’re not sure if I was born in Treviso, but I was certainly raised here,” she admitted. Illario leaned forward, silently offering an ear if she needed one. “Long story short, before you expect a sob story, Ignacio found me on the street trying to pick pocket him. I was successful, but it’s hard for an eight-year-old to outrun a grown man, especially a Talon. But he thought I had potential, so he inducted me into the Crows instead of whatever else would have happened.”

“But you don’t know what happened beforehand?”

“Not a clue. I remember the children on the streets I stuck close to in order to keep safe, but that’s it. Ignacio would often call me a miracle since it seemed that I was born on the streets.”

“He sounded like an asshole.”

“Oh, he was, and I hope he’s burning, wherever he is. Regardless, he never took me anywhere, and Viago wasn’t exactly in the position to travel much once he became Talon. Before then, I was too young to go anywhere on my own,” Isabella explained before smirking. “Regardless, everything worked out in the end, right? I’m on my way to becoming a Crow, even if it isn’t what I expected.”

“The unofficial motto of the Crows,” he chuckled as she nodded once. 

“So, what other questions did you have in mind for this fake first date we’re on,” Isabella wondered as Illario faltered a little. It was his idea, but the idea that this was for a job now made him feel disappointed. “I suppose we should know more about each other than what foods we like and where we want to visit.”

“Well, we know a bit about each other’s pasts now,” he offered. She shrugged, supposing that was true. “If you could mold a perfect spouse, who would they be?”

“Spouse?” Isabella chuckled. She wanted to tell Illario that she would never get married unless it was necessary. She had long ruled out romance as an option for her life. But that wasn’t part of the game they were playing. She tilted her head. “Someone who is caring and sweet. Maybe someone who will stick by me, even when I’m being stubborn or irritating.”

“That’s an easy list there, cariño (sweetheart).”

“What about you then, Signor So-Tutto-Io (Mister Hot-Shot)?”

“Well, she needs to be able to keep up with my antics. My teasing. You know, willing to joke around a little,” Illario answered, lifting one shoulder. “And she would have to be a Crow. That much is a given.”

“Of course,” Isabella chuckled, shaking her head. “I don’t think I can go around town, showing off my Crow leathers if we’re meant to blend in.”

“I meant in real life, Bella. Not for our make-believe plan,” Illario sighed, throwing his head back. She smirked. 

“I’m teasing you, signor, or trying to,” she informed. He whipped his head upright again as she rolled her eyes. “It seems that I need more practice.”

“Or I need to get better at reading you,” he suggested playfully. Isabella huffed in amusement before she grabbed her pack for their evening meal. 

If he didn’t know any better, he could have sworn that had been her attempt with flirting with him. It had been so subtle that it passed him by, and he missed it. He certainly didn’t want to miss it a second time. 

“And I’d be happy to let you practice whatever you wished with me, preciosa (precious),” he mentioned, sitting closer to her. She looked up at him before he held out his hand. She raised an eyebrow before handing him his portion, wary still of his words, but her walls weren’t up either. 

Illario waited a moment as he looked over the horizon at the fading sunset. It was a gorgeous purple color with a faint orange glow near the ground. The stars would be out soon, and he did enjoy looking at them before he fell asleep. 

“What was the name of the first person you kissed?” Illario wondered, turning towards her just to watch her choke on a piece of food. He tried to hide his smile, pleased that he could catch her off guard with simple questions he could ask anyone else. They might find him odd or strange, but they wouldn’t react the same way.

Isabella recovered quickly and took a deep breath as the blush returned to her cheeks. The tips of her ears started to burn again as she glared at the man for both the question and her reaction to it. As if he knew she would react that way. 

“Why do you want to know?” she asked snidely. 

“Because of that reaction right there,” he replied with a wide grin. She frowned and turned away from him. “Was it that embarrassing, cariño (sweetheart)? I can’t imagine I would know their name.”

“You wouldn’t know the name because there isn’t one,” she hissed, shooting him a scathing look. Illario paused before furrowing his brow. 

“No one?”

“No one.”

“Are you telling me...” Illario started as he sat closer to her. He gently used his hand to guide her chin so she would face him again. Her face was still a bright shade of red, and he could see a slight fear in her eyes. “That no one has kissed your beautiful face, not even once?”

“Oh, knock it off, Illario,” Isabella whispered, closing her eyes. She went to yank her head away, but Illario moved so he could cup her head with both of his hands. 

“It is a sin that no one has ever shown you proper affection, cariño (sweetheart),” Illario murmured, seeing tears start to well in her eyes. “You should be painted on Chantry walls to preserve your beauty. Poets and bards should write you into legend for your wit and dedication. What I wouldn’t give to feel your lips on mine.”

“If you kiss me, Illario. It can’t mean nothing. It must mean something,” Isabella whispered through narrowed eyes, but Illario saw a flicker of something more behind them. A flutter of hope. A glimmer of interest. 

For all their fighting, Illario should have guessed it was projection and deflection fueling her words. The gift of the coffee wasn’t just because she was a kind soul. It was more than that. Isabella was kinder than most Crows, but she had grown affection for him, which he had missed until now.

“Do you want me to kiss you?” he asked in a quiet voice, leaning in gently. Her eyes widened a little with his question, and the question seemed to scare her the most as her breath stopped. 

Illario waited with bated breath as her mind weighed her options. He hadn’t given her a lot to go on, but she gave him the ultimatum. If he kissed her, then he would treat her as a romantic companion with her setting the pace as she needed to. He wasn’t sure he had been anyone’s first before. 

After what seemed like an eternity, Isabella nodded her head three times as she watched him, almost bracing for him to release her to laugh at her. Illario only smiled before leaning in to meet her lips with his. 

Her eyes widened in surprise before they fluttered closed, and her gloved hands covered with his. 

Illario noted that she was inexperienced, as he expected her to be. Usually that would bore him, but the idea that he would be the one to teach her thrilled him. Illario found that he wanted to be her first in everything she would let him be, and he grew eager as he deepened the kiss, showing her through action. 

Isabella pulled away to breathe as Illario grinned at her. Her cheeks were flushed, but she wasn’t embarrassed any longer. She caught her breath as he played with one of her gloved hands, careful not to remove the glove. He had heard enough of Viago’s lectures to understand why the de Rivas were keen on their skin coverings. 

“So, was it worth the wait, preciosa (precious)?” Illario asked as she gave him a genuine, unguarded smile. Illario stared as his heart skipped a beat. It was the closest thing to staring at sunlight he had ever come close to. If he could see that smile every day from now on, he was sure he could do anything.

“More than worth the wait, cuore mio (my heart),” she answered with a certainty that would have made the strongest man fall to his knees. “Or is that too much?”

Cariño (Sweetheart), you can call me anything you want,” he repeated before leaning in to kiss her again. Isabella rolled her eyes before accepting the kiss, thinking that she could get used to this.

Notes:

mi querida - my dear
querida - dear
cariño - sweetheart
Signor So-Tutto-Io - Mister Hot-Shot
preciosa - precious
cuore mio - my heart