1. Why was Clive not surprised that Jennifer didn't look very beat up when the multiple rapes were over?
As others have stated, Jennifer wouldn't have to be beaten to be raped. The emotional toll of the event would not make Charles question that.
2. Are we to believe that Jennifer trolls the commuter trains looking for frustrated, horny married men with $100K that they can spare?
Yes, we are. She's looking for marks no matter where she is. She's working as a temp/assistant to Lucinda Harris, so, she's headed to her temp job when she sees an opportunity to make a connection with a man who may/may not be wealthy. But, her primary job is to find marks. If it's on the way to work on the train...great! Lunch hour...great! Commute home...great! I'm guessing when she's on lunch hour from her temp job she's sitting in the bars near the financial center...looking for marks.
3. How did Clive get into the prison with a weapon...presumably on multiple days?
As stated by others...clearly a non-metallic weapon, familiarity with the guards after teaching the course for several days.
4. Why is the blackmail money being kept in the sleazy hotel safe?
The hotel is a
huge part of the scam. The clerk is in on it, the security guard is in on it. They can control who is in what rooms on what floors when they're getting close to day of the rape. They can stage the hotel whenever & however they want. The fact that it's sleazy makes it even more believable. Anniston just has to make sure they are driving near the hotel, say "I can't do this", tell the cabbie to stop (so it totally looks random), and then say "ok, let's do it...hey look...a hotel!"
So they kept all the money there as it's an integral part of the scam. This is certainly not out of the realm of possibility.
5. What downtown hotel Chicago hotel -- not blatantly overrun with rats, pimps and crackheads -- only charges $46 a night?
Again, the hotel is a huge part of the scam. So what that it's $46 dollars.
6. And why are audiences always expected to believe that an otherwise intelligent man would pay blackmail in the vain hope that THIS payment will be the LAST?
To me, it's not a stretch that Charles will do almost anything to keep this away from the wife. They've got enough problems in the marriage and with the daughter's health that he would not want this to be known. I also think he's very naive that paying the blackmail will work.
Others have stated:
There is an issue of why go through with the complicated scam.
A scam with much less liability would be one where they simply tape Aniston banging the mark and then blackmail him into giving them money.
I believe LaRoche
likes to beat people and he & Anniston get off on having sex in front of other people. They do it for the money
and the excitement.
What if someone else in the hotel hears the commotion?
The sleazy hotel likely is not full all the time. The hotel clerk has a lot of control as to when the perfect time to stage the rape will occur.
Why did the clerk at the hotel not recognize Charles and warn Dexter, when Charles went back to the hotel alone?
If I recall correctly, he's able to get in the lobby and get to the stairs without getting too close to the front desk. On this point, it's more likely that he would run into Dexter.
And why didn't the cops that night place Charles in the area of the scene where Winstons body was found?
I'll concede one point on Winston's death. Blood clearly leaked from the car where Charles was interacting with the prostitute and the two cops. This would connect the car in the river and this incident. While this would give them a description of a "person of interest" in the case it wouldn't lead them to Charles.
On a side note, I put Vincent Cassels performance up there with Alan Rickman as Hans Gruber. I fully bought into the sadistic, yet charming Cassel being able to overpower and intimidate the timid executive who "cons housewives".
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