Macmillan Dictionary, which hyphenates the expression, says hail-fellow-well-met is an adjective that means ‘behaving actually in an extremely friendly method that is annoying or does not seem sincere’. So it packs rather many nuance right into a couple of familiar, if unpredictably arranged, words, generally indicating not so much a details amount of social intimacy as an assumption or screen of also a lot of it. It might be an expansion of the shorter expression hail-fellow (likewise Hail, fellow!, etc.), which the OED notes was both a greeting and also a descriptive expression offered in a range of constructions. The second component, Well met, was also a greeting: around ‘it’s excellent that we’ve met’, according to World Wide Words.
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If the expression sounds archaic or old-fashioned to you, you’d be ideal – it dates to the sixteenth century at leastern. Thomas Hardy used the shorter expression in The Mayor of Casterbridge (1886): ‘He crossed the room to her with a hefty tread of some awkwardness <…> and also with somepoint of a hail-fellow bearing’. The adjective’s definition is more transparent in Lord Delamere’s advice to the well-heeled in the late seventeenth century: ‘Let not your Servants be over-familiar or haile fellow through you.’
Sometimes, though, it’s not supposed negatively, and hail-fellow or hail-fellow-well-met conveys simple friendly familiarity, not an excess of it. This is possibly what James Joyce intfinished in Ulysses, once he defines newspaper men as charging at one an additional one moment and also ‘Hail fellow well met the following moment’.
Hail is an extremely old word which over the centuries has amassed multiple meanings in various grammatical categories: verb, noun, adjective, interjection. This last usage – where Hail! itself is a greeting or exclamation – goes back to roughly 1200, and also is hardly ever encountered this particular day. At least not in everyday discourse; Hail Mary is a devotional salutation used in a prayer of the exact same name.
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The connected verb hail, initially interpretation to salute someone or greet them with a Hail!, is roughly the exact same age, and survives in a method – we still hail a taxi, interpretation speak to it or entice its attention. And if we’re lucky the driver isn’t also hail-fellow-well-met.