I had a French teacher who used to like to proclaim that all teachers are really frustrated actors. Sometimes, I wonder if all romance novelists are really frustrated matchmakers. There’s a reason one of my college friends nicknamed me “Emma”. In real life, one’s set-ups have an irritating habit of fizzling, due to pesky little things like geographic constraints, timing, and the infinite variability of human character. One of the joys of being an author is that you can put your characters exactly where you want them, when you want them there, and watch them go.

The basic principle, however, is the same. Part of what I love about matchmaking is the psychological challenge it presents. It’s like sorting out an LSAT logic problem. You try to puzzle out exactly which aspects of a person’s character will make him mesh with the confusing kaleidoscope of attributes inherent to another human being. This was particularly true of the hero of my last book, The Seduction of the Crimson Rose, the ubiquitous Lord Vaughn.

Ever have those friends you keep trying to set up but keep failing? That was Lord Vaughn for me. When Lord Vaughn first plunged onto the page in The Masque of the Black Tulip, he was dallying with the idea of espousing the youngest child of the Marquess of Uppington, Lady Henrietta Dorrington. He was really dallying with the idea rather than the lady. It was clear that while he was intrigued, his affections weren’t strongly engaged. It struck me, though, that some of the aspects that drew him to Lady Henrietta—her plain speaking, her refusal to be intimidated by either his title or his supercilious manner—might also lead him to take an interest in her friend, Miss Penelope Deveraux, an outspoken redhead with a complete contempt for all the rules of decorum.

Ah, yes. I had great plans for Lord Vaughn and Penelope.

Wrong, wrong, all wrong. All my plot ideas for a Penelope-Lord Vaughn book stalled out after about the third chapter. The two, quite simply, had nothing to say to one another. Lord Vaughn might appreciate Penelope’s looks, but he had no respect for her—well, her anything else. His feelings towards Penelope began and ended with casual contempt.

It made me realize two important things about Lord Vaughn. First, while he himself might have deliberately flirted with the bounds of society, he still played by its rules, even as he transgressed them. He might toy with the illicit, but he had no interest in the unconventional. Second, everything about him, from his carefully coordinated attire to his double and triple entendres was rigorously controlled. Even his hedonism was played to a pattern and planned to perfection. Penelope’s complete lack of discipline would arouse Vaughn’s contempt, not his affection.

By then, I had moved on to the third book in the Pink Carnation series, The Deception of the Emerald Ring, where Lord Vaughn delighted my matchmaking soul by striking sparks with the equally rigorously self-possessed Miss Jane Wooliston. It seemed so perfect. Until it wasn’t. I had ignored one crucial factor. Jane might be as self-controlled, as clever, as calculating as Vaughn, but she had one crucial attribute that would never, ever mesh with Vaughn: a conscience.

In the end, I did find the perfect heroine for Vaughn (at least, I think I did—if you’ve read Seduction of the Crimson Rose, you can tell me whether or not you agree) but it took me three books to do it, three books of trial and error and process of elimination. The marvelous thing about it, though, was that it taught me so much, not only about Vaughn, but about the various characters with whom I tried to set him up.

Are you a matchmaker? Do you try to set up your friends? Do you speculate about pairing off the side characters in the books you read? Which characters would you pair off if you had the chance?