What is it in life that will push you to the point of doing something even when you aware the consequences will likely be? Raymond knew when he jumped that he would likely get hurt or die. What causes him to choose to do it?
With Rex, Raymond presenting an even more bizarre choice. A man kidnaps your wife/girlfriend/whatever and likely kills her. Even though Rex does not know she is dead, he knows it is likely the case. Rex's obsession was already apparent long before Raymond decided to do what he did. Rex was apparently willing to forgo revenge or anything else just to know what happened. Rex had to know.
So, I think the only thing that Raymond wanted to know was where the line was. How far would Rex's obsession take him? As he learned more and more information, at what point would Rex stop coming along?
Look at is this way. First, why would Rex even get in the car with someone who was likely a murderer? But he did, because he had to know. Would Rex try to turn Raymond in at the toll booth or would his need to know take him furter? After Raymond reveals himself as a sociopath, would Rex's obsession cause him to continue to try and find out? Think about it, after each possible out that Rex is giving, he learns more information about what happened. He had plenty of opportunities to stop. So, the situation builds until Raymond offers the most ludicrous offer he could offer. He had given Rex every indication that his wife was dead without coming right out and saying it. Then, with all of that information, he gives Rex a choice to find out what will happen even though everything indicated that going any further would result in Rex's death.
I think the entire ride was to take a measurement and to try to see if the obsession would carry Rex all the way to the end. And it did. Because there was no reason for Rex to believe that if he drank the coffee that he would live through the ordeal.
Fate plays into this as well. If Rex was fated to die, if it was unavoidable, then he would agree to everything Raymond wanted even if he knew he would likely die. So why not tell him everything? Anyone in their right mind wouldn't have drank the coffee, unless they were possibly predestined to do it. What better way to test that then giving someone every possible reason to turn away from that fate? If the still didn't, then no matter what either of them did or knew, Rex would die.
I am very tired and i might not be explaining myself correctly. But I think there are a lot of complicated things at play here. I don't think Raymond's goal was to kill Rex. The death was an incidental part of the larger questions. Raymond was testing fate and obsession, those were the things he wanted to know about.
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