How Gilmore Girls Do Money: Dean Forester

Gilmore Girls

“What’s this?” Caleb asked, holding up the notebook.

“Put that back,” Dean said. “That’s a Daddy thing.”

A year ago, Caleb might have done it; but now he was eight, and empowered by his status as swaggering second-grader, burping out Disney Channel catchphrases. He opened it.

“Stars Hollow, Labor Day Weekend,” Caleb read aloud. “The sunlight high over Doose’s Market—”

“Do-seys,” Dean corrected, automatically.

“As I sink into my saddle and leave both the sun and the stars behind me.”

Caleb paused, then laughed. “You wrote the F word!”

“Give me that,” Dean said, standing over his son and snatching the notebook out of his hands.

“I’m telling mom you wrote the F word,” Caleb said.

“Stop messing around and put those boxes in the corner like I told you,” Dean said. He could have put away the Christmas decorations five times faster than Caleb, but this was part of what it meant to be a family. To ask your child to do a chore and then watch as your child did everything he could to procrastinate.

After Caleb reluctantly moved the boxes from the top of the attic stairs to their corner, and after he ran down, free at last, to play games on the iPad, Dean sat on the top of the stairs with the notebook that he had shoved into his back pocket. It was crumpled, the same way he had crumpled it when he shoved it into his pocket a decade ago, the year he sold everything he owned except for his motorcycle and hit the road.

I lost the two great loves of my life in the same year, he had written. That was on the first night out of town, in some diner off the highway. He had tried to feel like Hunter S. Thompson, but instead he sat at a counter that looked too much like Luke’s. At least at this diner nobody turned their face when he walked in the room.

He read the Hell’s Angels book after Rory mentioned it once, when she was dating someone else who wasn’t him. It’s funny how he could hardly remember who, at this point. They all blur together into That Guy, the cool rebel guy, and Dean had once felt like that guy, so he got on his motorcycle and tried to feel it again.

He aimed for California and got as far as Illinois. He didn’t feel like the cool rebel guy, but he didn’t feel like the guy everyone hated, either; the guy who had broken two great hearts in the same year.

Every midwestern stop felt like another Stars Hollow; every diner and grocery store reminded him of what he had said to Luke before he left: “This town, it’s all you are, and it’s not enough.” He was talking about himself, of course, so he turned north, towards the one place in the state that wasn’t a small town.

The highway into Chicago was the most terrifying motorcycle ride of Dean’s life, so after he arrived he sold the motorcycle and got down to the business of finding a job. That Guy would have moved into a hostel or made a zine or started a business, but Dean had never not had a job, so he found one.

Dean had never not had a girlfriend, either—not even when he was married. He started dating Kirsten, who was both his boss’s daughter and the contracting company’s receptionist, but nobody minded. Dean was likeable. He had forgotten that when he lived in Stars Hollow. He wasn’t used to people smiling when he walked in the room, on time and ready to work.

He was married in a year, they put the down payment on a suburban fixer-upper in two, and Dean finished renovating the house just in time for Caleb to be born. In a few minutes his wife and his daughter would come back from the grocery store, and Kirsten would put a frozen pizza in the oven, and it would probably be one of those pizzas that came with cookies. Everyone would be happy.

Dean closed his notebook and thought he would put it back where Caleb had found it—or maybe in another box so Caleb wouldn’t find it again. Then he opened it and added one more sentence:

I found the great love of my life in 2006, he wrote. Her name is Kirsten Forester.

Previously, in How Gilmore Girls Do Money: Richard Gilmore.

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