and rory's writing is perfect

If Rory had told Dean the truth about the bracelet

DEAN: Hey, where… where’s your bracelet?

RORY: What?

DEAN: You’re not wearing your bracelet.

RORY: Oh.

DEAN: Where is it?

RORY: Don’t get mad.

DEAN: Why, where is it?

RORY: I…Dean, don’t get mad but I lost it.

DEAN: WHAT?

RORY: It was an accident.

DEAN: When?

RORY: What?

DEAN: When did you lose it?

RORY: I’m not sure.

DEAN: You don’t KNOW?

RORY: Please, Dean.  I’m going to turn the house upside down, it’s got be around somewhere.  You know I never take it off.

DEAN: You lost it and you didn’t even notice it was gone.  Just forget it.

RORY: Come on, Dean - I didn’t mean to lose it. I am so sorry.  

DEAN: Yeah, you’re not sorry enough.  You never are.

RORY: Dean, that is not fair! You know what that bracelet means to me.  I’d never hurt you.

DEAN: You’re hurting me right now.  I made that bracelet for you and you don’t even care that it’s gone!

RORY: Dean, you know I care!

DEAN: Yeah, the same way you cared about spending time with me when you want to build houses for Harvard or go to a bookstore.  You know, I’m not even surprised.  Forget it, Rory.  Go home and make a pro con list, or I know, go talk it over with your mother, or Jess, as you seem so chatty with him lately!

RORY: Dean, it is not about that! You know I didn’t lose it on purpose!

DEAN: You still lost it though.  You lost it.

Literati Headcanon Scene

Scene: Jess had just finished reading the part of Rory’s novel that was about him…

“So?”

Jess set the last piece of paper down and tried to swallow but his throat was dry. Without answering, he pushed away from the table and went to the fridge. “Want a drink? Beer or water?” he asked, turning his back on Rory while he gathered his thoughts.

“Water please.”

He grabbed a bottle of water and a beer and took them over to the table, setting the former in front of her. Then he opened his beer and sat down.

“You’re being eerily quiet,” Rory said with a nervous catch in her voice. “If I were a cartoon character, I’d be chewing on my nails right about now.”

Jess stared at his drink, his mind still racing with everything he’d just read. The writing itself was technically perfect—this was Rory after all—but it was what she’d revealed that had him so troubled. “I’m… processing.”

“If it’s too personal, I’ll change it,” Rory said. “Or if you want, I can omit—”

“No,” he said, his head snapping up. He blew out a breath, trying to remain calm. “Don’t take me out of your story.”

She nodded. “I didn’t mean take you out entirely. I meant just omit the part about your parents.”

“Oh.” He wasn’t that insecure boy anymore; at least, he didn’t think so. Still, a part of him had been so sure she’d have no qualms about erasing him from the book and, in turn, from history.

She flashed him a sad sort of smile. “Jess, if I took you out, my story would be woefully incomplete.”

— “Time After Time” by June Gray (available on wattpad).

I think Rory writing in Richard’s office was the perfect way for her to deal with her grief. In my opinion, she and Richard were always paralleled in a way that she wasn’t with Lorelai. Richard would have loved that she was using her grief productively to write about the family they were both so proud of.