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I was thinking about it in the context of romance, both as a genre and as a real-life event. For starters, as I mentioned before, I've made a new OKCupid account, and I like reading through profiles there and writing to interesting people. Profiles tend to fall into a few categories:
1. People I know I'd love to go out with, or at least be friends with.
2. People whose profiles indicate that they're totally not my type, but I can certainly imagine that they'll meet someone great for them. Not all of these people are perfect, by any means; some have physical or mental problems, or parts of their past they're trying to fix, but you can see that for someone out there, they'd be great.
3. People whose profiles don't have enough to figure out anything about them. (Might I mention, guys, that "ask me if you're curious" with no other info is a total deal-breaker. If you aren't willing to put any information about yourself on the profile at all, I don't want to talk to you and I don't care what you look like.) I assume some of these folks are new and they'll eventually start putting more in there, or give up.
4. This is the real heartbreaking category. These are folks who put up lots of stuff about themselves, but there's so little that indicates they'd be good to date, and so much bad stuff, that I can't imagine anything but them spending their life totally dateless. (This especially means you, Mr. "I HAVE A HEAD INJURY" profile, who can't seem to take no for an answer.)
So, why exactly is that heartbreaking? Possibly because I've gotten used to that old romantic cliche, "You thought no one would ever love you, BUT I DO." It's a cliche because people like a happy ending. "There's someone for everyone" is a saying-- but is it true? Are there people who are happier single, or would be happier single than in a relationship warped by their personal issues, if only they could manage not to make themselves miserable longing for something that wouldn't work?
One of the books I've seen that handles an un-romance very well is Mercedes Lackey's Four and Twenty Blackbirds. Set in her "Bardic Voices" universe (a pseudo-medieval society with magic), the main character is a constable tracking down a murderer, with the help of a bishop who employs him. In this world, Church officials can be women, but they're still sworn to chastity, poverty, and obedience. When the constable developed inappropriately warm feelings about his boss, he realized that she was the first woman he'd ever met who was extremely bright and shared his interest in history (in other words, that he'd be attracted to any woman similar to her), and that since she'd have to either break her vows and lie, or give up her position, to pursue a romance with him (and he wouldn't like her nearly as much either way), he decided that he wouldn't ever approach her about his feelings.
So, are there more books like this out there? The obvious sort of plot device for this would be the clergyperson tempted to break vows who doesn't, but it seems like there are a lot more reasons two people shouldn't get into a relationship even if they like each other. Any recommendations, folks?