When Vivienne van der Woodsen entered kindergarten, she refused to wear the official uniform. Instead, she wore what she'd been wearing all summer: her angel costume. She didn't play dress up as a princess like other girls; she dressed up as an angel with her white angel wings she had strapped to her shoulders. It made her feel like she could fly or do anything. She felt like something magical.

        When it was time for kindergarten, Vivienne was ever so stubborn. She was nervous about school and she didn't want to leave home. Her costume made her less anxious. All morning her mother, Lily, argued with her but she refused to wear the required uniform. Lily gave up and let her go to school in her costume that consisted of a long white sparkly dress that went down to the ground and her white angel wings.

     When she got there, since she was so young, Constance made an exception for it. And eventually she grew out of it. But that first day of school, what she did not know was that a boy at St. Jude's fell in love.

      Chuck Bass fell in love.

      Vivienne had clung to Serena, holding her hand tightly. Serena had said something to her that made her smile widely and that was when Chuck laid eyes on the girl a year younger than him.

       He was gobsmacked. Her fair blonde hair framed her face like a halo and the sunlight made her dress actually shine. She had a dimpled smile that was adorable. Even though it was a costume, he didn't know that at his age. Chuck was convinced she was an actual literal angel.

As soon as he saw his father after that day, he asked Bart if angels were real. Chuck even told him that he believed he saw one at school. His father said he was being ridiculous. But Chuck didn't entirely give up the notion until the third grade. And even then as the years went by, the thought of angels entered his head every time she smiled. Her smile might as well be some holy blessing every time she threw one at him.

       She was the only girl he was ever nervous to approach. The thought of being rejected by Vena, the nickname he gave her, was just too nerve-wracking. He elected to just be her friend.

           To Vivienne van der Woodsen, Chuck Bass was sweet. To Vivienne van der Woodsen, Chuck Bass didn't flirt. To Vivienne van der Woodsen, Chuck Bass wasn't a fiend. But to everyone else on the Upper East Side, Chuck Bass had a very obvious crush.

       Things had changed at the Shepherd wedding. Well, not change necessarily but Chuck had gotten to dance with Vivienne for the first time ever. And she asked him. He could hardly believe his own luck. 

       "Chuck," she called as she approached him. He had three girls around him that he had trying to convince to come upstairs with him. But then his world halted when he heard her delicate voice. "Will you dance with me?"

Whenever she came to these events, she was always around friends of Serena and Chuck was always nice. Vivienne thought of him as kind. Serena would always roll her eyes whenever Vivienne mentioned it. She didn't understand why.

Chuck stood stunned when he turned to look at Vivienne. Words got stuck in his throat as he gazed at her and her baby pink dress.

"I mean, unless you don't want to..." she fumbled with her hands nervously.

"Of course. Of course I'll dance with you," he replied as he gazed at her doe brown eyes and stepped forward. "I'd be an idiot not to."

She blushed before taking his hand and guiding him along to the dance floor. He was all too happy to follow. He played the strands of her hair from behind as they went.

        As he danced with her, the girl of his dreams, a smile that no one had ever seen on his face before took over Chuck Bass. His heart raced being so close to her and her infectious smile as he twirled her around. And one dance turned into many more.

Then she was leaving with her mother as Lily asked where Serena was. Vivienne didn't know and Lily just sighed as they exited.

"Your sister," Lily shook her head. "Let's hope she, at least, gets in at a decent hour."

"I'm sure she will, Mom," Vivienne reassured. She was always the dutiful daughter.

Vivienne looked back to give Chuck a wide dimpled grin one last time before she left which made his heart skip a beat. He was left standing there with a dazed smile that was absolutely ridiculous but that was what Vivienne van der Woodsen did to him.

After that night, he thought he had a chance with his dream girl. When Serena disappeared and she was suddenly overwhelmed with students curious about where her sister went, including Blair, Chuck defended her.

"You must know why Serena left. Tell me," Blair demanded.

"Leave her alone, Blair," Chuck swooped in. "She said she doesn't know."

"I don't believe that."

"I don't care. Leave her alone," there was an edge to his voice.

Blair huffed but nevertheless left and Vivienne let out a sigh of relief. She turned to Chuck with a grateful smile, "Thank you."

"You're always welcome, angel," he formed that lopsided smirk that made her stomach feel all fuzzy.

She blushed a deep red and Chuck gained a proud smirk before he tilted his head, "Come on. Let me take you home. Get you away from the vultures."

"Okay," she smiled as she tucked a strand of her hair behind her ear. She walked off with Chuck and he resisted the urge to wrap his arm around her shoulders. But he did open the door to his limo all too eagerly like a puppy.

After skipping school that day, despite him just taking her home, there were whispers about her and Chuck. She suddenly gained the popularity her sister had but she didn't know how to deal with it. And she didn't know how wicked some girls could be.

When her freshman year at Constance had ended, Chuck thought he'd get the chance to get closer to her during the summer in the Hamptons. But she had disappeared just like Serena. She was reportedly in Miami. In the Upper East Side, though, there were always secrets.

AN: so yeah here's a little beginning. Chuck is a literal simp for her and that's not going to change. Also Eric won't be the one in Ostroff Center. He's not lonely since Vivienne is around. And the reason Vivienne got admitted is not going to be revealed until season two