Growing up on a farm, I always considered harrowing with a positive connotation since it was the process making the rough ground smooth. But, I used it today with the negative connotation when mentioning a harrowing experience.
I checked out the OED and confirmed that the denotation of lacerating or cutting was operative in both cases. And, I realized my positive connotation came about because I did not care that the soil was cut or lacerated; who would? But, I had associated it with the positive result of smoother ground. (I also realized that if I fell off the tractor and was the one being harrowed, I would consider that very negative).
Other than positive or negative connotations dependent on a particular person's point of view (i.e. the death of Osama bin Laden, Barack Obama is a good president, etc.), do other WayWorders have pet words which have a particular sense of denotation but can then have both connotation senses due their own shifting point of view?
Emmett
The word special comes to my mind. I can use it in the traditional positive way, or ironically, as did the Church Lady, or euphemistically, as in Special Education or Special Needs.
My wife watches a lot of cooking, designing, and fashion shows. Quite often, when a judge is asked for an opinion, they'll say something like "That's an interesting [whatever]."
My impression has always been that's just a polite way to say "I don't like it, but I don't want to be negative or actually criticize it."
So if we're starting a list here, "interesting" fits in just like Glenn's "special" and EmmettRedd's "harrowing." I'm sure there are MANY more examples. Very interested to hear some other examples. It is a curious type of usage that definitely depends on context.
Heimhenge said:
My wife watches a lot of cooking, designing, and fashion shows. Quite often, when a judge is asked for an opinion, they'll say something like "That's an interesting [whatever]."
My impression has always been that's just a polite way to say "I don't like it, but I don't want to be negative or actually criticize it."
Churchill supposedly came up with a standard response whenever someone showed him a baby and expected him to gush over how adorable it was. Beautiful, ugly, or just plain funny-looking, he'd say "My, that is a baby!"
Just to show what a dweeb I am, instead of thinking of other words like this I was thinking, when I read the opening post, that even a harrowing experience can be a positive one. The Bible talks about God putting us to the harrow, and it clearly means an agricultural implement—but the intent is to break up hard ground (that is, myself), and the outcome, regardless of how it feels at the time, is a better me.
(In Proverbs it says "reprove a wise man, and afterward he will thank you". It doesn't say anything about his response at the time 
.)