The phrase “legendary naïveté” is something I first used years ago to describe my uncanny inability to recognize when a woman was interested in getting to know me better or, in rare cases, actively trying to seduce me. The classic example of this happened when I was 23 and taking a walk on a country road with a woman I’d just been fixed up with that night. We raced to a stop sign in the dark and when we got there she said “My bra came unhooked.” She generously offered to let me hook it, so I reached under her sweater and did exactly that.

There are other examples that would make this quite an entertaining and revealing blog entry, but for now I want to talk about how my legendary naïveté affected my initial efforts to publish a novel way back when.

In the summer of 1983 I wrote the first draft of my first novel, and a few years later I finished a much-improved new draft. Bob Smith wasn’t a bad little first effort. It was a literary fantasy that dealt with an assuming college student getting pulled into an adventure involving parallel universes and the search for an immortality potion. Rounding out the cast were five great 19th-century American writers—Poe, Hawthorne, Melville, Whitman, and Twain—who, in this book, were literally immortal.

Here’s where my legendary naïveté comes in. As I was crafting my query letter, I was absolutely certain that I had the hook that would make a publisher say “Heck yes, please send me your entire manuscript post-haste.” The hook, in my mind, was the fact that some of the great names in literature were characters in the novel.

I mean, if you work in publishing, you hold these guys in high regard, right? You’re thinking “I’ve got to at take a look at a novel that has Mark Twain as a character,” right?

Alas, nobody thought that.

Did I expect anyone to call me with a multi-book deal just because Mark Twain was a character in my first novel? Nah. But I kind of hoped my query would be opened by an old English major with fond memories of Huck Finn and Moby Dick, one who might think “Now this sounds like a fun read.”

I have a collection of about 50 rejection slips confirming that I kept missing that particular English major’s desk.

Bob Smith is still around and is due for another rewrite soon. I don’t think I’m naïve enough anymore to waste any more query letters on it, though, so look for it on this site by and by.