This is a question that's been on my mind for a long time, though I do not want to claim originality for it, since Gkarlives seemed to be asking something similar. Here are the assumptions: You come home from a long day at work and you want to relax. You do not want a broken heart at the end. You do not want to have clinical depression because of a book. (You also do not want to feel like you're choking on sugar. But sugar aside, since usually sugar isn't so bad.) Another necessary assumption, so that this discussion doesn't turn into a mere rant against badly written or badly structured books, is that the books we talk about are generally high-quality (where by quality I mean things like good writing style, existence of a nice plot, character development, etc...). Here is the basic question: What factors make a not entirely happy end truly heartbreaking? Is it ever the case that though a book is wonderfully written and had a strong impact on you, it is so distressing that you wouldn't want to read a book like it again? Or at least, not when you're looking for a nice book to pass an evening after work? Is it ever the case that the book is truly heartbreaking but you would want to read another like it anyway? What distinguishes these two possibilities? I will note here that I have encountered heartbreaking books of both sorts. These question might be very personal and we may or may not find commonalities. I would gladly hear opinions. Some of my opinions: On SciFi: I find that SciFi in general is unbearably tragic, so I rarely read it. I feel I must make a list of works from which I draw this generalization: all of Ray Bradbury, Dying of the Light by George RR Martin, Ender's Game by Orson Scott Card, Dune, Nightfall by Silverberg. I feel that SciFi is the perfect genre in which to portray the failings of human nature, futility, meaninglessness etc. We see people quite like us, who because of technology do not have many of the problems we might have. You dont see SciFi heroes dying in an earthquake in general. Stripping away things like natural cataclysms and a lot of chance, we are left with pure human nature. Thus a level of technology controls for many factors like fate that might make for tragedy in other genres. On fantasy: I feel that fantasy tends to be not at all like that, and it is fantasy that I pick up after work to relax. I will also list some of the fantasy I read: ASOIAF by George RR Martin, all by Robin Hobb, all Rhapsody books by Hayden, WOT by Robert Jordan, everything by Jaqueline Carey, everything by Julliet Marillier, a lot by Guy Gavriel Kay, Lotr and the Silmarillion by Tolkien... Possibilities of what makes a book distressing: Sex and violence: I think that neither the amount of sex and violence nor how graphically they are described has any bearing on how tragic a book is. Kushiel's series has tonns of either of them, but it was not distressing. Dying of the Light didn't really have either, but it was very distressing. I could give many other examples. Writing style: I think this is one of the most important aspects. I think in a lot of fantasy the upsetting effects are buffered by the song-like epic writing style that makes sex and violence aesthetically pleasing. SciFi does not tend to have this style. It is a lot more matter of fact, and thus more depressing. Plot twists: Some things are just upsetting, though it is not at all trivial to list exactly what they are or to determine if there is any commonality between them. I would very much like to hear opinions here. I don't think death or violence in itself distresses me in fantasy or SciFi. I must have become used to it. What seems more distressing to me are things like characters never learning information that they really really should know about, lies about things of import that are never caught, betrayals of people who do not expect it, manipulation of the innocent to vile ends, destruction of the beautiful, apocalypse, futility, yet another illustration of how life is meaningless, a character walking into certain death and dying. Characters?