My Dying Mother Wanted to See Me Engaged Before Christmas. So I Asked My Best Friend’s Sister to Pretend

My name is Theo Lancaster. I’m 51 years old, I’m a venture capital investor, and according to a business magazine, I’m worth about 2.3 billion dollars.

I have never been engaged.

I’m not proud of that, and I’m not ashamed of it either. I’ve had relationships. I’ve had a prenup drafted three times and never signed one. Every time, I’d get to the edge and step back.

My mother, Eleanor, has never understood it.

She lives on our family’s old apple farm in the Hudson Valley, ninety minutes north of Manhattan. Sixty acres of orchard, a stone farmhouse from 1790 and the best cider donuts in Dutchess County.

Last November, her doctor called me.

Pancreatic cancer. Stage four. She had until spring, maybe.

I drove up that night. She was sitting by the fire in her favorite chair, wrapped in a blanket, completely calm.

“Theo,” she said. “I have one wish.”

I sat down next to her.

“I want to see you engaged,” she said. “Just engaged. Before Christmas. I want to know you won’t be alone.”

I couldn’t say anything.

“Promise me you’ll try,” she said.

I promised.

Then I drove back to Manhattan and called the only person I could think of.