“I get it now, she’s everything I’m not.” She says as a few tears slip out from beneath her lashes.  His subconscious realizes at this moment that she’s unconsciously mimicking a line from the Royal Tenenbaums, one of their joint favorite films. When he replays this conversation in his mind later, this will break his heart.

Pam experiences heart break over and over again.

She looked over the boxes with wide eyes, overwhelmed by all the choices. Words like clear and easy were jumping out at her and she had no idea what to do because this was the furthest thing from clear or easy that she had ever done.

Title Courtesy of a Muse song.

Pam’s hands grip his shirt, and he looks up the ceiling. He hears Pam let out a sigh as she continues to cry, the tears sliding down her cheeks. He thinks for a minute she had fallen asleep, the bags under her eyes suddenly obvious, but no, she stays awake.
(Isn't as angst-y as the summary, I promise) 

A now-AU post-Cocktails story. I went back and did some retouching. Angsty Pam and Jim.