The Radical Grammarian, James Lyle, is nonplussed by the following sentence: “Fortunately, this was a voyage of discovery that Slate was willing to fund, leaving me in the prelapsarian position of having mine and my friends’ inebriation underwritten by Microsoft.”
Dealing a glancing blow to the dreadful “prelapsarian,” he homes in on the collective possessive, “mine and my friends’.” Unquestionably that’s wrong. But “my and my friends'” sounds prissy, “me and my friends'” isn’t right either, “I and my friends’,” “my friends’ and my,” what to do, what to do?
The great H.W. Fowler, mentioned approvingly here before, discusses a similarly sticky matter, the proper number of a verb when a neither and a nor member disagree. Neither you nor I…is? are? am? The technically correct answer is “am,” but Fowler has a better idea:
The wise man, in writing, evades these problems by rejecting all the alternatives — any of which may set up friction between him and his reader — and putting the thing in some other shape; and in speaking, which does not allow time for paraphrase, he takes risks with equanimity and says what instinct dictates.
So had our Slate author written “having my friends’ inebriation, and mine, underwritten by Microsoft,” no one could have quarreled. This simple solution seems not to have occurred to the Grammarian. Of course if it had, we wouldn’t have been able to enjoy his perorations on the subject. Or mine. (Link from Jessa of Bookslut.)