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In my experience, with such cases the best chance is to track down who added the sense using the diff function and find out what they intended to mean. If it's an IP, we're screwed as IP addresses change periodically. --Mglovesfun (talk) 15:02, 6 April 2011 (UTC)Reply
Mglovesfun kindly poked me in the direction of this discussion. I can't think of an unambiguous example of that sense, but here are the examples other dictionaries give:
Webster 1913 "To disappoint the hopes of; to deceive; to tantalize; as, to mock expectation. Thou hast mocked me, and told me lies. Judg. xvi. 13. He will not ... Mock us with his blest sight, then snatch him hence. Milton."
Webster's New Universal "to lead on and disappoint; to deceive; to tantalize; as, the weather mocked him"
John Ogilvie's old (1883) Imperial Dictionary "To fool; to tantalize; to play on in contempt; to disappoint; to deceive. 'To mock the expectations of the world.' Shak. Thou hast mocked me and told me lies. Judg. xvi. 10. Why am I mock'd with death, and lengthen'd out To deathless pain? Milton."
Writing about the line from Othello "It is the greene-ey'd Monster, which doth mocke The meate it feeds on", Heath says "'Mock' certainly never signifies to loath. Its common signification is, to disappoint."
Both lines from Milton seem like clear examples of "tantalize". The verse from Judges seems to mean "deceive". Collocation with "expectations" may be the best bet to find examples of it being "disappointing", eg 1812, The Critical Review or, Annals of Literature, page 190: The French revolution indeed is a prodigy which has mocked the expectations both of its friends and its foes. It has cruelly disappointed the fondest hopes of the first, nor has it observed that course which the last thought that it would have pursued. — Beobach06:38, 7 April 2011 (UTC)Reply
This is definitely what the word used to mean, but it's hard because many of the examples are now interpreted as the modern sense of the word. The OED says this early sense is ‘now largely merged’ into later senses – always quite difficult to deal with. They don't mark it as obsolete, but their last citation is from Hardy's Tess of the d'Urbevilles (so more than 100 years ago): ‘Swayed by the antipathetic wave which warps direct souls with such persistence when once their vision finds itself mocked by appearances.’ Ƿidsiþ07:47, 8 April 2011 (UTC)Reply