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When Cassandra first met Rapunzel, she hated her. She hated the princess's optimistic outlook, her belief that there was good in everyone, her persistent attempts to be her friend. And yet, Rapunzel somehow managed to win her over. Their distance became close friendship, and somewhere along the line, Cass had fallen in love with her. She kept her feelings a secret, knowing everything would be ruined if Rapunzel found out. Their friendship would be over, Rapunzel would think she was disgusting, and Cass would never see her again. Rapunzel already had a boyfriend, why would she want someone like her?
Then Rapunzel and Eugene broke up after his second proposal. They said they didn't know if they were right for each other anymore. Cass tried not to feel happy, and she focused on supporting Rapunzel through the fallout instead, but a part of her wondered if she had a chance with her.
Although Rapunzel and Eugene didn't get back together, Cass still didn't tell Rapunzel about her feelings for her. As the group neared the Dark Kingdom, her love became obscured by the same hatred she felt before she got to know the princess. Rapunzel was falling back into old habits, refusing to listen to her and overstepping her boundaries. When Cass took the moonstone, she knew she was destroying any chance she had with her, but she didn't care. She didn't care what bridges she burned if this would get Rapunzel to face her mistakes.
Despite everything Cass had done while she was under Zhan Tiri's influence, Rapunzel never gave up on her. She never gave up on anyone. She was so forgiving to Varian, to Frederic and somehow, to Cass. Her forgiving nature made Cass like her even more, but she couldn't stay in Corona with her. She had to leave to find both herself and her destiny. She knew she'd return someday, but she wanted to explore the world outside of Corona first.
When Cass returned a year later, Rapunzel and Eugene had long since realized their relationship wasn't going to work. Eugene and Lance were together, but Rapunzel wasn't dating anyone. Cass finally found the courage to confess her love for the princess, and they dated for almost a year before Cass was ready to propose. She bought a ring from a nearby shop and made her way to Rapunzel's room. She knew Rapunzel loved her, but she'd never been more terrified.
"Cassandra? Are you alright?"
Cass had been so lost in her fear that she didn't notice when Arianna approached her.
"Yes, I'm fine, Your Majesty," Cass said quickly, trying to end the conversation as soon as possible.
"Are you sure, dear? You look a bit tense."
Cass sighed softly. Of course Arianna saw right through her. She knew there would be no point in lying now, so she decided to tell Arianna what she was doing.
"Well, uhh, I'm actually going to propose to Rapunzel. That's why I was going to her room."
"I'm sure she'll say yes," Arianna said, looking into Cassandra's eyes with a gentle smile. "It's easy to see that she loves you, more than she's ever loved anyone."
"T-thank you, Your Majesty," Cass replied, "that means a lot."
"No need to thank me. As far as I'm concerned, you're already family."
Cassandra knew, as she neared Rapunzel's room, that what Arianna said was true. Rapunzel did love her deeply, and she was already a part of her family in every way that mattered.