Saying 'Goodbye' Is the Hardest Part of an E-mail

It feels like the 18th century all over again. All that daily correspondence, all those long hours spent hunched over a desk, composing some thoughtful missive about one's dowry or the Jacobite rebellions. Signed, "Yr humble servant."

Same deal now, basically, except (obviously) we're not clutching quills; we're writing a passel of e-mails and clicking send on ye olde BlackBerry until our fingers bleed. And something else isn't quite the same: Unlike the heroes and heroines of epistolary novels, we aren't blessed with time-tested formal guidance on the correct way to sign off.

"Best"?

"Cheers"?

"Sincerely"?

For Daniel Morrison, CEO of the D.C.-based international relief nonprofit 1Well, the wrong sign-off posed an impediment to deeper romance. "I sent an e-mail to a girlfriend, and she was very put off by me signing off with 'Regards,' saying that I sounded very 'emotionally detached,' " Morrison says via e-mail. "We did break up shortly thereafter, so maybe she was right."

Will Schwalbe, co-author with David Shipley of "Send: Why People Email So Badly and How to Do It Better," warns, "You can really do a lot of damage, even with a careless closing. And one of the terrifying things about e-mail is: You may never know."

But you may well feel the chill.

"If you have been writing to someone 'Best' this and 'Best' that, and you get an e-mail that is a little colder, a little hostile, and they sign 'Sincerely,' that does mean things aren't so good," Schwalbe says. " 'Sincerely' is the one that says, 'There's a problem here.' "

And, one may well wonder, does "Cordially" ever mean anything other than "My hostility is only thinly veiled"?

And when, e-mail-wise, is it too early for "Love"? Does "Fondly" ever belong in business? Is "Cheers" too mock-Brit? Too alcoholic?