A modern gentleman pities those born between 1965 and 1979.
He based this on the fact that they were “too old to be young and too young to be old.” But Generation Y — and every other — is also
literally sandwiched between the generation that came before and that which followed.
So the distinction that makes Generation X pitiable must be figurative, which he thinks is exemplified by each generation’s usage of “whatever.”
To Generation X, the word signifies indifference: All outcomes are effectively the same, so choices don’t matter.
(A modern gentleman of Generation Y responds, “Refusing to choose is making a choice, and it’s annoying.”)
“Whatever” communicates ambivalence to Generation Y: Outcomes couldn’t be more different but will be accepted as the price of making choices.
(To which a modern gentleman of Generation X says, “Doesn’t the fact that outcomes inevitably will be accepted mean all outcomes are effectively the same?” and mutters, “… perfect example of the naivete of youth.”)