It seems like you're trying to use SENT in sentences 1 - 3. I'm not positive it's incorrect in all of them, but it's definitely awkward and unnatural. I think the problem is that using a fairly complicated clause after SENT doesn't work. There's always going a better/clearer way to say it. Using SENT this way tends to work better when something simpler after it. Often it's something metaphorical. Scrolling social media endless nearly sent me to the madhouse. Buying a Ferrari nearly sent her to the poorhouse. NOTE: 'madhouse' and 'poorhouse' are antiquated terms, only used in expressions, not literally. If I heard that song one more time, it's going to send me over the edge. Sentence 4. basically seems okay, but you should probably omit AND before ESPECIALLY.

I would correct them like this, to make them sound more natural: 1. Tom's talk nearly reduced me to tears. 2. Tom's way of speaking was almost offensive. 3. The way Tom spoke made me think he was launching a charm offensive. 4. We can't bear the agony of not know what Tom did, especially when he was all alone.

Sentences can have many kinds of flaws: 1. they can be grammatically wrong 2. they can be grammatically correct but have no clear meaning 3. they can be grammatically correct, have a useful meaning, but use words that are poorly chosen. 4. none of the above, but they just don't sound good to native speakers. 1. Your sentences have two true grammatical errors: "an offensive person", not "a offensive" "a charm offensive", not "charm offensive" 2. The meaning of #4 is not clear. What does "when he was all alone" refer to. Is it the time when Tom did things? Is it the time when we cannot bear the agony? 3. In three of your sentences, "sent" is a poor word: a better word is "caused" 4. "That way of Tom's to speak" is correct, but does not sound good. Instead, say "Tom's way of speaking"

1. "What Tom said nearly reduced me to tears." 2. "Tom's way of speaking seemed offensive." / "I was offended by Tom's way of speaking." 3. ? 4. This one depends on what you mean. "We cannot bear the agony of not knowing the things Tom did, especially when he was all alone" implies that we are especially considering, out of all the things Tom did, the things Tom did all alone. OR "We cannot bear the agony of not knowing the things Tom did, especially considering he was all alone" implies we should especially consider that Tom was all alone. “Tom's talk" 聽起來有點奇怪。 "Tom 說的話" = "What Tom said" 3號 我不懂你的意思。