I talked a lot about understanding your characters through looking at what might work well for them in terms of romance, but as Brickwall pointed out yesterday, I never really went into much detail on explaining how. Here are a few tricks for figuring out what kind of places and what kind of forms a given character might be looking for love in.
What sorts of characters do they seem to do well with (or badly with) non-romantically? This one’s been one of my favorite ways to figure out characters; when I was doing this exercise as a game with one of my friends, both of us intuited a couple of one NPC’s tendencies from which of the existing characters he seemed to have resonated well with. This is good for picking up on qualities, personality types and behaviors that work well with the character; if he has nothing but scorn for people who act before thinking in your experience, why would he like that tendency any more in a romantic partner?
Skills they respect tend to fall into one of four categories. The first, of course, is skills they themselves have, particularly the ones that require training (shows dedication to the skill, which means the character being admired clearly values it) or qualities that they themselves find admirable. The second category is skills that they can appreciate by parallelism to the skills they have (a swordmaster admiring the control of a calligrapher, for instance). The third (somewhat less common, or at least less effective for a long-term connection because it’s just as likely to breed resentment) would be skills that the character does not have, but realizes she needs to team up with someone who does. And the last is skills that the character doesn’t necessarily need, but wishes she had. (There are other cases, but these seem in my experience to be the most common.)
Figuring out how character history relates mostly boils down to drawing parallels, and works equally well for both attraction and revulsion. And all it requires is a character who isn’t a tabula rasa! In most character backstories, there will be one or more characters whom the character has strong feelings about, whether those feelings are “I want to be her when I grow up” or “Get her away from me!” What follows, then, is a two-step process. First, figure out what traits are particularly representative of that character (for people who get inside characters’ heads easily, specifically for the character this exercise is being done for). Just having the traits can give you a skeleton of possibilities for the character’s ideal partner (or absolute dealbreakers, going the other way); applying them to other characters can help to determine which possible pairings either have a leg up on the competition or are likely to, as far as this character is concerned, fizzle before they have a chance to begin.
The impact of the social system should probably go without saying, particularly given all the missing-the-original-point retellings of Romeo and Juliet out there. They’re from different social classes! They’re from warring families! He’s predator, she’s prey (funny how it rarely seems to go in reverse)! Their union is physically impossible without shapeshifting magic! And no, this insurmountable difference does not mean that they will totally make it and their love story will be the greatest evar and…. ’scuse me a sec, I’m a bit ranty on that topic.
[Distant sounds of curses on formulaic authors with tired cliches, followed by returning footsteps] All right, better.
This isn’t all the possible ways of figuring out what would work with your characters by a long shot, but for people who can’t just jump into the minds of their characters, they make good jumping off points. Have fun!