You weren’t supposed to like her.

You were supposed to expose her.

The magazine had given you one assignment — a feature on the “hidden rot” beneath Manhattan’s wealthiest zip codes. The Upper East Side, all polished façades and photo-ready perfection, was your target.

And no one embodied that better than Lily van der Woodsen — socialite, art patron, philanthropist, and mother of the infamous Serena.

Your editor called her “the crown jewel of hypocrisy.” You just called her your next story.

When you first met her at a charity event, she was everything the tabloids promised. Graceful. Controlled. The kind of woman who smiled with her lips but not her eyes.

She recognized you almost instantly. “You’re with The Manhattan Review, aren’t you?”

You nodded. “Just covering the event.”

“Of course you are,” she said, with a polite half-smile that said she didn’t believe you.

Still, when you asked for an interview, she agreed.

“Everyone wants to write about me,” she said, her tone dry. “Very few want to understand me.”

You took it as a challenge.

The first interview was supposed to last an hour. It went on for three.

You sat across from her in her penthouse, the skyline reflected in the glass walls behind her. She spoke carefully — every word chosen like a brushstroke. But the longer you talked, the more the edges softened.

You asked about her gallery, her past, her children. She asked about you.

“You seem too sincere for a journalist,” she teased.

“And you seem too human for the headlines,” you shot back.

Her laughter filled the room — low and unexpected. “Touché.”

That night, as you packed your notes, she said, “Be kind in your writing. Not just to me — to anyone. Truth doesn’t have to destroy.”

You should have known right then you were in trouble.

Weeks passed. You spent more time with her than you should have. Lunches at her gallery. Coffee at The Palace. Late-night calls “for one more question.”

Somewhere between interviews and confessions, the line blurred.

She told you things off record — about her mistakes, her regrets, her loneliness. And you started seeing her not as a headline… but as a person.

Then, one evening in her townhouse, as you scrolled through your notes, she said softly: “Do you ever feel guilty?”

“For what?”

“For digging into people’s lives.”

You hesitated. “It’s part of the job.”

Her gaze was steady. “And what if you find something worth protecting instead of publishing?”