Matthew Hanley — whose interests include winking emoticons, awkward conversation killers and the “let’s do this in 7 emails or less” rule — was pressured to resign after a someone hacked into his email account and discovered the pervy exchange below. In a good-bye letter to the school, Hanley states that he had separated from his wife months before after realizing that he was gay.

His would-be fuckbuddy, Michael Hulshof-Schmidt — himself a headmaster of another Oregon high school — has managed to hold on to his position thus far. As far as the email exchange goes, we admire Hulshof-Schmidt’s hardball flirtation tactic of calling Hanley “trash.” But Hanley’s closing statement (“I am already ruined”) confuses us.

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The Most Hilariously Emo Conclusion to an E-mail Flirtation (Manhunt Daily)
“Not Safe For Work” (Willamette Week)