I noticed this most acutely when I reread The God of Small Things by Arundhati Roy last fall, previously one of my all-time favorite books, but no more. I still love the writing and the language - and even the story to a point. But it's an overwhelmingly tragic and sad story, jumping about through time to slowly reveal why the twins are possibly irreparably damaged, wandering aimlessly through the ruins of their lives. Are the young, or at least those fortunate enough to have never had to experience true strife up to that point, more drawn to tragedy? Do they find it more romantic, more appealing somehow? I must have, but I definitely don't anymore.
Roy paints a story in which almost all of the 'adults' during the twins' childhood have very few redeemable qualities, and the twins suffer the consequences of their actions within a prejudiced society built around the caste system. Their adult selves are basically ghosts, hollowed-out husks of what they could have been. It's still a beautiful novel and definitely worth reading, revolving around a rich, colorful culture but also a strikingly rigid society based on strict interpretations of class. Just don't expect to come away feeling all happy-gooey about humanity (not that I ever do, really, but it's nice to at least find elements of redemption, or even just the possibility of redemption).
The first time I read this, on the very strong you-have-to-read-this-Right-Now recommendation of a friend, I believe I was a fresh-faced new college graduate, newly supplanted to New York City, wandering anonymously through the bustling, gritty humdrum of the city. (Or it was my last spring break during which I visited NYC - either way, for some reason I associate my first reading with the city.) I was fairly naive and extraordinarily trusting, though also painfully shy. I'm not really many of those things anymore, at least not nearly to the degree I was then. Still fiercely introverted but not so much shy, still occasionally clueless but the awfulness of which humanity is capable no longer shocks me to the same degree. Tragedy is just tragic; it's not romantic, it's usually not enlightening, and it's always always unnecessary, and, apart from natural disasters, always completely avoidable. Perhaps that was the ultimate point of the novel, one that touched me then in a way that seems obvious to me now.
Other rereads have produced similar results, not always that I enjoy the novel less - sometimes I like it much more. Vonnegut's fatalism seems much more smack-you-in-the-face now than it did 15 years ago. And it's not just specific books but even types of stories. Forbidden love, especially when it's forbidden because one or both the parties are married, is just eye-rollingly tiresome, and not romantic. Have you had this experience? Have you noticed your tastes changing over time to the point that rereads are completely different experiences?