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"You know the real reason I keep on asking, Rapunzel?" Eugene spoke, gently, as they sat on her window seat, after yet-another rejected proposal, watched by the moon outside the window. "It's not for a crown. Or even just for the beginning of my blissfully settled monogamous comfort with you which I am one hundred percent ecstatic about."
He sighed. "See, I've realized two things about your parents, since we started living here. Your mother is a kind, warm, emotionally intuitive person… and your father is a man who consistently makes his absolute worst choices and doggedly sticks by them even when they explode in his face when he tries to think about the Kingdom first."
Rapunzel opened her mouth, and closed it, initial upset turning to confusion, before she had words.
"…what does that have to do with us, Eugene?" She finally asked.
"You just got back to society, but. I just.. very frequently wonder how many chances I have to ask you, before you become one of those decisions, Rapunzel," he admitted, "For someone of your station to marry someone of no political advantage, purely for love, is rare. A luxury. And your parents love you, but sometimes I feel like your father's just waiting for me to screw this up, or for you to get tired of me."
"oh… ohh, I'd never let that happen, Eugene."
"I know. I know. I just worry about your… hand being forced, no pun intended." He held her hand.
"Gee, Eugene," came a dry voice , "maybe she should let you have her maidenhead ahead of time, as a strategic measure."
"Cassandra?!" He flushed. "How long were you standing there in the corner?"
"Long enough for you to reveal more thought than I thought you were capable of."
"Har de har har." He paused for a moment, though, his eyes narrowing as he tapped his chin with the other hand. "…that's actually not the worst idea she's had though, Blondie."
Cassandra gaped. "…Fitzherbert are you crazy?"
Rapunzel flushed. "…I'd like to hear what you mean by that, Eugene."
"Okay, so, think about it," he began, looking between the two of them. "In the dead of night, we handle it: we find the location, and sneak off together, enjoying a whirlwind night of illicit passion somewhere we're certain we won't be caught and legendary outlaw Flynn Rider steals one last time. I don't care about the whole 'saving it' thing, guys can barely tell if it's there or not—"
"You said that with a lot of confidence, Fitzherbert."
"Let me finish. To the kind of people of station we're worried about? It's not just a dealbreaker, it's an insult. King Frederick gets any ideas, we quietly let it be known and suddenly Rapunzel's hand to anyone else is no longer politically advantageous. And if he doesn't, no one ever needs to know but us. It's a perfect crime!"
There was a pause as the idea hung in the air.
"Eugene you sound so… excited about this," Rapunzel spoke with a flush, "Like it's an adventure."
"Raps you're not seriously— he's planning your first night as lovers as a heist. That's not… unromantic and degrading to you?" She spoke, incredulous. "People look at women who would rather give that up like- like they're broken, damaged goods. That's what he's counting on, if it ever has to come out."
Rapunzel frowned. "Why would I care about what someone who would reduce me to that thinks, Cassandra? I know Eugene won't. I know you won't. I don't think Father will, as angry as he might get if we have to tell him this."
Cassandra cursed internally as she felt a flush come to her cheeks seeing the princess so willfully question things she had accepted as unquestionable.
"This isn't… me 'giving up,'" Rapunzel continued. "This is me making a choice, to protect my future. Think about how you trained to fight. Isn't it better to have a defense you don't need, than to need one and not have it?"
"…if you're going to try this scheme you're going to need me," Cassandra realized. "I already know, I know the castle better than anyone and I know the guard shifts."
"I know the guard shifts too! I did successfully heist a crown out of this place."
"Uh huh. And you think my dad didn't immediately change things up because of this, mister legendary outlaw?" Cassandra pointed out with a little smirk. "Besides. You were dropped in on a rope and done in twenty seconds. I don't think that's what you have planned for your first time with Rapunzel."
Finally Eugene's turn to flush and sputter.
"Cassandra!" Rapunzel giggled.
"I'm just saying, if that's the plan there's ways to lose it yourself that would be a lot more of an experience, princess," Cassandra spoke, "But I'm your lady-in-waiting, and I know you, Rapunzel. If this is what you want you're going to find a way and I might have an idea. There's a spot above the stables that… is popular with the serving staff. Eugene still has his guard uniform, and Rapunzel, you're the right height and build to fit in one of my dresses. As long as no one gets too close, you should be able to get there with no real problems"
"Wait, wait." Eugene looked concerned. "If she's in your clothes and we're seen then-"
"Then it'll be a couple members of the help sneaking away to enjoy each other's company. No one will do anything about it," Cassandra insisted.
"But they'll talk about you," Rapunzel realized, "Cassandra, I could never."
Cassandra gave a little smile. "Let them. It's… just talk, after all, right? I know what the people who care about me think."
Rapunzel's arms were warm and tight, a sudden surprise for her lady-in-waiting to find wrapped around her. "Thank you, Cassandra."
"The night guard changeover's in 20 minutes," Cassandra said, flushing as she eased out of the hug, "That'll buy you the time to slip out unseen. But we'll need to work fast."
Rapunzel nodded. "Right."
"You can handle your part of things, Fitzherbert?"
He nodded. "Absolutely. I'll be waiting by the stairs during the changing of the guard."
It took much of the time to exchange Rapunzel's dress for the blue lady-in-waiting dress, and hide as much of the princess' golden hair as they could under the veil and down the back of the neckline. "The next changeout after this one is four," Cassandra continued, "You'll have plenty of time and be able to tell when you need to move when the-"
"I can handle telling time out there. Stable loft has a window. I charted stars and the moon in my tower. I'll know."
Cassandra chuckled. "Right. Good luck out there with your… defense."
Rapunzel smiled. "Thank you. And thank you for… being a part of the team."
"Hey, my job as princess detail's to look out for you, Rapunzel. Just doing my duty."
"I love you too, Cassandra."
Before the lady-in-waiting could process what was said, the princess was out the door, and the last heist of Flynn Rider was in swing.
Cassandra hadn't left Rapunzel's quarters. The words were in her head, circling. Had Rapunzel meant it? Had she misspoke? She felt nerves roiling inside her. And Rapunzel had gone with her blessing- with her plan- to consummate her love to the thief. Cassandra felt sick by the time 4 AM rolled around and she could start beginning to expect Rapunzel back. When the door did open and Rapunzel quietly closed it behind her, the princess was quick to note the tension in Cassandra's posture.
"Cassandra, what's wrong? Did someone see I was gone?"
Cassandra looked up. "I… Rapunzel, I need to ask you something."
"Yes?"
"Can you tell me the last thing you said to me before you left?"
"I love you too, Cassandra?" She sat down on the bed beside her.
"Why did you say that?" Cassandra asked.
"…because I do," Rapunzel spoke, flushing.
"And… and too means you think I love you. Why? I've never said that."
"You don't have to tell someone to let them know you love them, Cassandra."
Cassandra opened her mouth, and paused. Damn, she had a point.
"But you and Eugene…" she protested.
"I can't imagine what my life would be like without either of you now that you're here, and I'm not sure I ever want to find out."
Cassandra flushed.
"And.. Eugene…?"
"He's seen me around you. He knows."
The alarm bells were ringing in Cassandra's ears. "He's told you this?"
"…no, but…"
"We have to talk. The three of us."
At 4:20 AM, after the success of the Last Heist of Flynn Rider, Eugene was quite ready to embrace the few hours of sleep on the palace bed. Unluckily for him, it was not yet to be. Just as he got comfortable, having slipped out of the guard armor and into a suitable sleep attire, a knocking at his door. He groaned and stretched as he rose back up and ambled to the door- to find Cassandra and Rapunzel waiting for him.
"Are you crazy? If anyone sees you at my door at this hour-"
Cassandra pushed past in, and Rapunzel closed the door behind her.
"Hey, hey, easy, Cassandra- what's wrong?"
"Rapunzel, tell him."
"Did something go wrong? Is her dad mad at me now?" He guessed.
"Cassandra, calm down," Rapunzel spoke, taking a breath. She looked nervously between the two of them. Cassandra eased out of Eugene's space.
"Rapunzel? What's wrong?" Eugene asked gently. He cupped her chin, tilting her head up. "It's okay. Whatever it is."
"…I love you both," she spoke. Eugene was surprised, looking from Rapunzel, to Cassandra, and back, momentarily speechless.
"…I don't know why I'm surprised," he spoke after a moment. "From the day we met in the tower, I could see a few things about you. I saw that you knew exactly what you wanted. I saw that you had the drive to pursue it. And I saw… that you had a light and a kindness and love inside of you that… challenged and continues to challenge all the ways I look at the world. I… don't know how you navigate something like this. You're a princess and you'll still… kind of have to get married at some point for the continued peace of the kingdom by, you know, having a royal family tree that keeps going. But I know I meant it when I said you were my new dream."
Cassandra gaped at the level of sincerity and sensitivity Eugene managed in the face of this. For just a moment, she began to see what Rapunzel saw in this man.
"And… how do… you feel about this, Cassandra?"
"I…" she exhaled. "I think it's a lot. And it's a risk. And it's dangerous for all of us."
"I'm sensing a but," Eugene commented.
"But I'd be lying if I said I didn't want to try and make it work."
Rapunzel beamed, pulling Cassandra close as the three embraced around Rapunzel.
"We'll just have a lot more jobs to plan."