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Diane dreamt twice   

Has it occurred to anyone besides me that Dan is speaking to Diane when he says "It's the second one I've had, but they're both the same."?

I think he means that Diane has this same dream twice. The central questions, then, are: When in relation to the incidents recalled in flashback, did she dream? When, in relation to the dreams did she have the flashbacks? Did she have all of those flashbacks between the two dreams? … after the first dream? … or some between the dreams and some after the second dream? I suspect that the lights out in the Adam/Camilla makeout in the front seat, indicates the passing of a night between that flashback and the next; that could mean that she slept and dreamt the second time between those two flashbacks. The events recalled in flashbacks after the second dream could have occurred before or after the first dream, but she definitely went to the party before the first dream and paid Joe after the first dream.

Diane had at least one initial face-to-face (or perhaps doggie style) meeting concerning the contract with Joe. At that meeting, which isn't shown in the movie, he described the blue key but didn't show it to her. That is when he deposited eight butts in her ashtray; he probably smoked a couple of cig's after each roll in the sack with her. This meeting may have been either before or after the engagement party at Adam's.

Then she dreamt for the first time. Like Dan, the Cowboy also was talking directly to Diane. If she did good, by not paying Joe for the hit, she would not have the dream again; so the Cowboy would not look in on her twice. When she got up from the first dream, the key was not yet on the coffee table. All the flashback events precede the first dream, but Diane has the flashbacks after the second dream, because they all happen after we see the blue key on the table.

Some time after the first dream, Joe dialed Diane's extension on an in-house phone system, connected to that big answer machine beside the bed; Sierra Bonita is probably a hive of call girls, each with one of those big answer machines; Joe may have been Diane's pimp. The ringer on the answer machine is turned off, but the phone by the red lamp rings. Joe tells Diane to meet him at Winkie's in five minutes (so the cops won't have time to set up surveillance, in case she's setting him up). If this is the hairy-arm call to #4, then Diane must have anticipated it the first time she dreamt. That is possible, since it's not the first time Joe has called her, and there were eight butts in the ashtray when she went to bed before the first dream. However, I believe the fact that the butts are precisely the same and even the window light is the same in dream and flashback is DL telling us the call happened before the first dream. If the hairy-arm call preceded the first dream, it must have been Joe calling about an additional meeting at her place. It could not have been her first contact with Joe, unless the butts belong to someone else; but no one else is shown in the movie with brown-filter cigarettes.

Diane does bad by paying Joe to kill Camilla; days later, she finds the blue key in the arranged place, brings it home, sets it on the coffee table, goes to bed and dreams again. She is awakened by the neighbor coming for her dishes and the red lamp. The shade of the lamp is packed with the dishes; we see her wrap up the cord, with a socked attached, a bulb in the socket protected by a paper thing. The lamp base is very small; I couldn't see it on my TV; perhaps it is also packed with the dishes. The red lamp was in #17 before the switch; but I don't believe we see it before the switch.

Diane hallucinates that Camilla has come back from the dead and has a series of flashbacks. The knock on the door panics Diane, and she kills herself. Actually, it was not detectives at the door, but Ed McMahan and the prize patrol. 

I don't believe Diane dreamt after she shot herself. The blue key, indicating she did bad, was on the table when she got up from the second dream. If she did bad before the first dream, the Cowboy's warning would be pointless. The only thing that comes after she shoots herself is Silencio.

When the Cowboy looks in the second time, the corpse is rotting and the mattress is ripped. Maybe somebody, like Joe, though Diane had more cash hidden in the mattress.