This makes me think of the book "The Paradox of Choice." Essentially it argues that we live in a world of infinite choice, which should make us happy, but actually makes us miserable. When you don't have options, or have very few, you don't spend a lot of time regretting your choices, because you didn't have any. But once people have a hundred different options, suddenly they can imagine all of the ways things could have been better. According to the book, we actually experience this imagined alternative reality as a real loss. You can imagine a lot of reasons this sort of psychology would have been evolutionarily useful—you're more likely to take your scenario analysis seriously if you really feel the pain—but it malfunctions badly in this paradise of choices we've created.
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