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A night to remember

Summary:

Eugene is determined to make this friendship work, Cassandra... slightly less so. But Eugene's finally happened across an idea that might just be crazy enough to work.

After all, what's a few drinks, games, and confessions among friends?

Chapter 1: The setup

Chapter Text

“I’m sorry. You want to what?”

“Oh, come on, Cass. You heard me.”

“No, no. I heard you, I just wanted to make sure you heard what you were saying, and to who. Because I’m starting to think there’s something actually wrong with you.”

It was odd enough for Cassandra that she found Eugene not only wilfully coming down to her room in the castle, but acting polite about it? At first, she believed it was a trick; it could have been some kind of ploy to lower her guard for a prank, or something. She didn’t expect Eugene Fitzherbert to just walk right in.

Especially not with a request.

“Seriously, Cass. Even scary, knife-wielding glaciers like you move around every once in a while.” Eugene retorted. He poked gently at one of the knives set out on a tray before the handmaiden. At least until Cassandra swatted his hand away.

Weapon maintenance was usually a calming time for her.

This... was not one of those times.

“Ow! Even you have to have fun sometimes, right?”

“I was doing just fine, Fitzherbert. At least until you blundered in.” Cassandra pointed out, running a cleaning cloth against the blade of one of her daggers. As if to prove the point, she showed it off once she was done; it was clean as a whistle.

Eugene mustered his ‘unimpressed’ face. “Yeah, I can tell. It’s like the world’s sharpest stamp collection in here.”

Cassandra groaned, of course he would insult her hard work. She set her things down and finally allowed Eugene her full attention. “Look, I don’t even understand why you’d think coming down here is a good idea, let alone trying to pull me into whatever stupid little plan you have cooking in that little head of yours.”

“First of all, it’s not stupid Cassandra, it’s genius. A purely original thought from the mind of Corona’s greatest former thief!”

A wry smile graced Cassandra’s lips that time. There was skepticism in her eyes. “You came up with that all on your own?”

“…Okay, it started as a suggestion from Rapunzel, but I’ve made it my own, and you know what? I think both she, and myself, are onto something here!”

Cassandra frowned.

“Raps... wants us to spend time together,” she asked. “Again?”

“Yup.”

“Doesn’t she remember how that went the last time?”

“Yup!”

Both of them needed no urging to recall the day the two of them had spent locked in a prison cell, only to end up almost at the mercy of a couple of old acquaintances. All in a slightly misguided, but goodnatured, attempt by a certain princess to build a foundation to their friendship.

Cassandra had thought her vast repertoire of colourful descriptors for Eugene and his looks, skills, and personality were enough for that alone.

Eugene disagreed.

“So we’re in agreement then? Ugh,” She feigned disgust, as if the mere thought brought her no joy. “Besides, she knows we like different things; I enjoy keeping things orderly and getting my chores done, and you like to...?”

She trailed away, looking at him for an answer. Or not, really.

“I enjoy many, many things. So many things, in fact, that you would not believe it. And that is why I want to extend this formal offer.”

Cassandra’s rolling eyes answered him. “Raps doesn’t count as a ‘thing’.”

Eugene huffed. It was the sound of someone nearing defeat. Music to Cassandra’s ears.

“Will you at least consider this offer?”

She scoffed. “I don’t believe this, you’re really trying, huh?”

“You will see that I try at many things, yes.” Eugene nodded.

She couldn’t believe him. And she couldn’t really believe herself when she felt the odd twang of curiosity. “And what, pray tell, is it that you want to spend time with me doing?”

“I’m so glad you asked! See, there’s this tavern down near the bridge that serves the best-”

“Pass.”

Eugene raised a perfectly tweezed eyebrow. “Seriously? Not even a regular, old tavern trip? Lady, you’re making it really hard to pick out a friendly activity.”

“It’s just...” Cassandra paused as she searched for the right words. “Let’s just say if anyone recognized me out there, it would probably end poorly.”

“Ohh, what?” He eyed her, digging for something, anything to hold her to. “Were you banned from all the taverns in the kingdom? Under guard law?”

Teeth grit. A glare was levelled at him.

“The answer is no, Fitzherbert. I’m not going.”

Eugene threw up his hands. He was becoming exasperated at Cassandra’s exasperation. “Of course! I mean, here I am trying to extend the grape branch of goodwill-” He watched Cassandra roll her eyes.

“Olive branch.”

“-And you manage to turn it into yet another thing about work.”

Cassandra finally stood up, her expression unchanged since the moment the “dashing” “rogue” pushed in her door – Which, now that she thought about it, was still hanging open. That nearly drew her attention away from the matter at hand, but she snapped back.

“Maybe because some of us actually value that hard work, and the respect we get from it,” she moved across her room to the ‘war’ cabinet-- the one so overstuffed with weaponry of every dangerous persuasion that Eugene had to wonder just what all of it could ever be for –and started to place the cleaned blades back where they belonged. “Sorry, Fitzherbert. Your idea might have, possibly, potentially, actually have been interesting... maybe. But I still can’t go.”

Eugene’s brow knit. There was an itch on the back of his head, but not one of those regular ones that he could simply scratch away. No, this one went deeper than that.

It was a mystery – scratch that. Cassandra was a mystery. Everything about her was some shade of enigma, with secrets held tighter to her chest than a duchess’s corset. But that was fine. He’d undone his fair share of those.

“Can’t or won’t?”

“..Both.” Cassandra stated as blunt as the sound of her cabinet doors being slammed shut.

Too bad she couldn’t end this conversation so easily. Because she was immediately retorted with something that made her spin around.

Just five words.

“...Wait, you’re not scared, are you?”

Cassandra immediately balked at that, eyes widening. “Wh- Oh come on! Of course not!”

“Because, if you are- and I’m just saying if -then that’s totally fine! I’m not gonna drag Cassandra the Iron Handmaiden out to anything she can’t handle. Like a little excursion into town in the evening.” He admitted.

There was a subtle shift in the room. A shift in the light, the temperature, whatever it was Eugene could feel it, and he could read it across Cassandra’s face. She scowled at him, but there was thinking going on behind those piercing eyes that made him almost immediately regret his words.

Almost.

If there was anything Cass couldn’t back down from, or himself for that matter, it was a challenge.

He held his breath for a reply, and hopefully not a knife in his gut. He’d already had more than enough of those in his lifetime.

He wasn’t expecting her to drag that handmaiden headdress off her head and slump back onto her bed

“You really want to know why I can’t go out?”

Eugene didn’t answer, but he didn’t need to. His eyes were imploring enough.

Cassandra sighed, not for the first time in this conversation. “After that little... ‘you know’ with Raps-”

She knew he knew. About the girls’ excursion outside the castle walls; the reason why Blondie was blonde again, and that she had told him after all his prying. Picked up on it with just a few, slightly off mannerisms one day. He would never be used to the fact that Cassandra, of all people, could read him like an open book, while he was left to skim the dust cover.

Eugene swallowed and nodded for her to continue.

“People are... suspicious. If anyone figures out that I’ve been shirking my duties, and connects me to what happened, I’ll be sent to a con-”

“Convent. Yeah, I know. You’ll never be able to follow my girlfriend around again.” He’d gotten the talk from Rapunzel on their ride out of Old Corona. Nobody deserved to have their life ruined for the sole fact that they wanted Rapunzel to be happy.

Not even Cass.

“So, that’s it?” Eugene asked, as though it really was.

“That’s it,” Cassandra concluded with a sense of finality. “Unless you can somehow make it so nobody in the kingdom knows who I am.”

“What, like you actually talk to people outside the-?”

Eugene’s eyes widened. Oh. Oh, that was it. This was even better than any of the snappy comebacks he’d been cooking up for her. This was going to be even more brilliant and helpful.

“Wait- that is it! Another brilliant idea from the mind of Eugene Fitzherbert!”

Not even her long-suffering groan could get him down now. He was on a roll. “Really? You’ve already solved it?” She asked.

“Yup! Trust me, Cass, you are not going to regret this!” Eugene fixed the sullen Cassandra with his best grin and a thumbs up.

“Don’t say that. Please.” But nothing was going to stop Eugene’s mood now, and Cass was simply along for the ride. “How exactly do you intend on getting me in and out of the castle without anyone finding out I’m gone?”

Crossing his arms before him, he looked like the picture of brilliance. At least, he thought so. Ah, Eugene Fitzherbert, you’ve done it again.

“Simple. It won’t be ‘Cassandra’ leaving the castle tonight.”