drailing
pp. Composing and sending an embarassing e-mail message while inebriated. [Blend of drunk and e-mailing]. Also: d-railing.
drail, d-rail v.

Example Citations:
A male friend of mine in Victoria enjoys passionate "drailing" (emailing when drunk) with a girl he's only ever got er, fleshy with in the organic world once.
—Genevieive Read, "You've got mail madness," Hobart Mercury, May 11, 2005

Generation Y's version of drunk dialing is d-railing, a term meaning e-mailing while drunk.

"Drunk e-mailing gives me a chance to say what I want without anyone hanging up on me," said Lola, who was interviewed by The Chronicle but did not want her real name used because of sensitivity about her job. She noted that most drunk e-mails have more substance than drunken-dialing conversations, which are often used to try to hook up. Lola started d-railing eight years ago, and though she said she spell-checks her messages, most drunk e-mails can be easily identified by their grammar and punctuation errors or the time they were sent.
—Heather Maddan, "TiPsY TyPiNG," The San Francisco Chronicle, December 25, 2005

Earliest Citation:
So without further ado, we present the DailyCandy Lexicon IV:

drailing:
E-mailing when drunk — i.e., drunk e-mailing.
—"Lexicon IV," Daily Candy NYC, October 22, 2002

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