You’d been best friends with Serena van der Woodsen since your first year at Constance. She was golden — effortless charm, wild hair, that laugh that made people turn their heads. And through her, you were often invited into a world you didn’t belong in — penthouses, weekend trips to the Hamptons, charity galas that felt more like fairytales.

That’s where you met her mother. Lily van der Woodsen.

At first, she was intimidating — poised, always perfectly composed, a woman who carried her name like armor. But beneath the control, there was something soft, something tired, something you recognized in yourself.

She noticed it too.

The first time you spoke alone was one rainy afternoon. Serena had rushed out to meet Dan, leaving you in the penthouse with a cup of tea and your sketchbook. Lily passed by and paused when she saw what you were drawing.

“That’s… Serena?” she asked gently, her voice touched with surprise.

You nodded, closing the book a little too quickly. “Just a sketch. I was bored.”

She smiled faintly. “You’ve captured her perfectly. That mixture of innocence and chaos.”

You laughed nervously. “Guess that’s what happens when you’re best friends with a hurricane.”

Lily chuckled softly and sat across from you. “You sound like me when I was your age.”

You tilted your head. “You?”

Her eyes softened. “Yes. Reckless. Hopeful. Always trying to hold on to something real before the world tells you not to.”

Something about the way she said it — quiet, almost nostalgic — made you feel like she wasn’t really talking about Serena anymore.

After that day, Lily began to linger a little longer whenever you were around. She’d ask about your classes, your art, your future. She’d pour tea for you when Serena wasn’t home.

And sometimes, her gaze lingered too.

Once, after dinner, you caught her watching you from across the table — not judging, not assessing, but studying. Like she was remembering something through you.

“Has anyone ever told you,” she said softly, “that you look at the world as if it’s going to break your heart?”

You froze, unsure how to respond. “Maybe because it already has.”

That earned a small, sad smile from her. “You really are too much like me.”