I am feeling a bit distraught. I just finished reading One Story Issue #136, "Number Stations" by Smith Henderson. It was beautiful and compelling but also devastating. A lot of bad, sad things happen to people in that story, even if the author leaves room for a little hope and kindness. (I do recommend reading it, if you can stomach some despair. See Henderson's interview with One Story for some background.) "Number Stations" got me thinking about endings. And author holds a lot of power in an ending. If the reader is still with the story by that point, the reader probably cares about something. The author most likely has some emotional grip on the reader - which means that the reader is vulnerable.
When I was a child and I dreamed of some day being a writer, I promised myself I would always write happy endings. I remember feeling like the world owed us happy endings, like readers who opened their hearts to love characters deserved to be rewarded. In practice, this has turned out to be pretty difficult. After all, it's easy to write a story with a sad ending. Stories are about conflict and conflict has inertia; it is a boulder rolling through the lives of the characters. The easiest course is to let that boulder plow through the characters, knocking them over like bowling pins. Far more difficult is to craft a realistic diversion, a way out. But that's what happy endings are.
I think it's very stylish now (and it has been for decades) to have sad endings. After all, irony is ascendent and maudlin cheerfulness seems too earnest for people who aspire to the intelligensia. But as a reader, I hope for a skillful exit from the conflict that a writer as set up. And as a writer, I aspire to manage that escape. Especially as I hope to fulfill the oath I made as a child and the implicit promise to please an important reader of mine. It is a difficult promise to hold to.