1. Well, the gist of Wormwood's letter appears to be some examples of 'feeble' sins, and some complaints to Screwtape about how hard it is. I'm pretty sure Wormwood is trying to push the blame off and say it's not his fault if it all goes wrong.

2. I think the dual definitions are definitely in use today, but they're contradictory ones. The truth can't contradict itself, though, so there's definitely something wrong with Screwtape's definitions.

3. I think Screwtape means that the sorrow and horror is considered real, while all the joy and wonder of the world is to be considered a false construction.

1. What do you think Wormwood wrote his uncle in his last letter?
Based on Screwtape's statement about wondering if Wormwood thought he'd been sent into the world for his own amusement, I think Wormwood wrote about somethings that are pleasurable for demons but not really related to his work with the patient (something about the general evil of the times). Wormwood clearly didn't tell Screwtape exactly what was going on. I think he complained a lot about how hard it was and probably talked about trying his best. I wouldn't be surprised if he complained that the Enemy was blocking him or complained about how his education hadn't prepared him.
2. Do you agree with the dual definitions of "real"?
I agree that the word can be and is used in both senses. The sense of the word that makes the most sense to me is the one about sky diving because that encompasses the whole experience - the facts and emotions that go with it. I don't see the other definition going away anytime soon. How often do we hear things like "Wait until you get into the real world"? Real (and forms of the word) need to be assessed based on their context and we must remind ourselves not to put too much value into the word. We must remember that we experience pleasures and pains. Any experience can be broken down into facts (what happened, what was seen, etc. ) and what was felt. This reminded me of part of the lyrics for the Facts of Life TV show:
You take the good, you take the bad,
you take them both and there you have
The Facts of Life, the Facts of Life.

source: http://www.lyricsondemand.com/tvthemes/ ... yrics.html

3. What does Screwtape mean by "they are more often in the predicament of paying for the cake and not eating it?"
I'm not really sure. I think it might have to do with working for something and then not enjoying it - like buying house and working extra hours to pay for it. On the other hand, Valia's definition makes a lot of sense too and seems to fit better with the context. People are "paying" for anything positive in their lives by all the pains that they are going through but are too focused on the hardships to spend anytime focusing on the pleasures. I'm still not sure what Screwtape means but it doesn't sound pleasant in any case.

1. What do you think Wormwood wrote his uncle in his last letter?
He seems to have complained about his problems with the Patient and then listed off a number of things that he was trying to achieve.

2. Do you agree with the dual definitions of "real"?
Yeah, it seems to make sense, I have heard it used in both contexts.
In fact, I think most people use real as in the emotional definition most of the time.

2. Do you agree with the dual definitions of "real"?

Yes, people do use the word "real" a bit hypocritically, don't they?

3. What does Screwtape mean by "they are more often in the predicament of paying for the cake and not eating it?"

The opposite of eating the cake and having it too. Screwtape says that people accuse one another of wanting this. In context it might go like this: "You always think of children at play being real life but bodies splattered on the pavement as being less real somehow!"

As Screwtape points out, people are actually more likely to believe that the horrible things in life are real, but the pleasant things are not.

4. The following reminded me of The Silver Chair:

Keep him comforting himself with the thought of how much he will enjoy his bed next night.

Sounds a bit like Jill and Eustace, right?

5. Also, Lewis said something that is very nearly like what I said in response to a previous letter and I'd like to share it:

Whatever men expect they soon come to think they have a right to: the sense of disappointment can, with very little skill on our part, be turned into a sense of injury.