Macmillan Thesaurus, which hyphenates the expression, says hail-fellow-well-met is an adjective that implies ‘behaving actually in an extremely friendly means that is annoying or does not seem sincere’. So it packs fairly a lot of nuance right into a couple of familiar, if unpredictably arranged, words, normally indicating not so much a specific amount of social intimacy as an assumption or display of as well a lot of it. It may be an extension of the shorter phrase hail-fellow (also Hail, fellow!, etc.), which the OED notes was both a greeting and a descriptive expression supplied in a range of constructions. The second component, Well met, was also a greeting: approximately ‘it’s great 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 right – it days to the sixteenth century at least. Thomas Hardy offered the shorter expression in The Mayor of Casterbridge (1886): ‘He crossed the room to her through a heavy treview of some awkwardness <…> and also via 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 with you.’
Sometimes, though, it’s not intended negatively, and also 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, as soon as he describes newspaper males as charging at one one more one moment and also ‘Hail fellow well met the following moment’.
Hail is a really old word which over the centuries has amassed multiple interpretations in different grammatical categories: verb, noun, adjective, interjection. This last use – wright here Hail! itself is a greeting or exclamation – goes back to approximately 1200, and also is hardly ever encountered now. At leastern not in day-to-day discourse; Hail Mary is a devotional salutation used in a prayer of the exact same name.
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The associated verb hail, initially interpretation to salute someone or greet them via a Hail!, is roughly the same age, and also survives in a way – we still hail a taxi, meaning call it or lure its attention. And if we’re lucky the driver isn’t as well hail-fellow-well-met.