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I recently made the unfortunate mistake of apologizing for having been "disingenuous" towards a friend. Luckily my friend was generous enough to assume that I had mis-spoken and ask for clarification; because somehow I had gotten the notion that disingenuous was based on the root of generous rather than genuine. While I had been sincere enough in everything I'd said, it was a lack of generosity in repeatedly assuming the worst intentions in everything they did that I needed to be apologizing for.

Since then, I've been wondering if there even is an English word that means what I wanted to say. I've come up with many individual words that apply to one degree or another, but not something that easily sums up the demeanor I was trying to describe.

Is there a single word that would carry the connotation of "always thinking/assuming the worst" in someone, not in the sense of being deliberately malicious but merely in the sense of being distrustful and bitter and hence reading the worst possible connotations into every situation?

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Cynicism: Assumption of the worst about people or the outcome of events.

There is a small difference between cynicism and pessimism. A cynic assumes the worst, but analyses to find if the worst is true. A pessimist, on the other hand, is negative right from the start to the finish, and may not necessarily delve to find if his assumption is true.

Cynicism = skeptical objectivity - Trust but verify. Pessimism = negative subjectivity - It may not be so.

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I think rather that cynicism is used to describe the basic belief that humans act solely out of self-interest without thought for others. –  Jim Mar 6 '12 at 8:29
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I'd call that pessimism.

an inclination to emphasize adverse aspects, conditions, and possibilities or to expect the worst possible outcome

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According to wiktionary, a cynic is a person "who believes that all people are motivated by selfishness" or "whose outlook is scornfully negative." This is a bit different than what you asked about, even though the previously-suggested word cynicism is right on-target because it includes among its several senses "an emotion of jaded negativity, or a general distrust of the integrity or professed motives of other people".

Also consider bloody-minded, "behaving in a way that makes things difficult for other people; refusing to be helpful" and paranoid, "exhibiting extreme and irrational fear or distrust of others".

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