Last night (23 December), I had dinner with colleagues. As I left, my boss said ‘Merry Christmas’, which sounded perfectly normal. This morning (24 December), my wife said ‘Merry Christmas’, which didn’t. The major difference is that my boss had/has no expectation of seeing me again closer to Christmas Day. I assume that my wife has every expectation of seeing me again closer to Christmas Day. The only reasons why she would not (one of us is dead or seriously injured or ill, or has deserted) would render Christmas un-merry.
So, the second requirement for saying ‘Merry Christmas’ is that is it the last time you expect to see that person before the day. But the first requirement is that it must be a reasonable length of time before. You can’t say ‘Merry Christmas’ as soon as the in-store decorations go up (seemingly increasingly earlier each you). But if you don’t say ‘Merry Christmas’ in the last week before Christmas, people might think you’re a grump.
Related to this is the second wish ‘Happy New Year’. We can certainly say ‘Merry Christmas and a Happy New Year‘ now, but when can we say ‘Happy New Year’ by itself, either in the days between Christmas Day and New Year’s Day, or into January. I will be returning to work on Monday, 9 January, so can I still say it then? Perhaps the easiest solution is not to say anything (see ‘people might think you’re a grump’, above).
I don’t like merry at the best of times – it has connotations of frivolity and drunkenness, which I think are not appropriate for Christmas. I would like say ‘a joyful and blessed Christmas’ but people might look at me strangely. Actually, I would like to say ‘solemn Advent’ but people would look at me strangely.
People don’t and can’t look at me on the internet, so I wish you a joyful and blessed Cristes mǣsse. (Oh, I don’t like the universal pronunciation of ‘Christmas’, either, but I’m certainly not going to say ‘Cristes mǣsse‘ in public.)
(Remember – the twelve days of Christmas are Christmas Day and the eleven days after, so don’t buy your Easter eggs until 7 January.)
Never Pure and Rarely Simple 
My mum, as well as my nana, maternal aunts, uncles, and assorted cousins always wished us a Happy Christmas. In fact, most of the Christmas cards I receive from my Australian relatives still say Happy Christmas. Happy, to me, has none of the negative associations connected to merry.
At any rate, I wish you and your wife a Happy, Joyous, and Blessed Christmas however you spell or pronounce it.
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Saying ‘Happy Christmas’ *by itself* is always possible, but a soon as you pair it with New Year, you almost have to say ‘Merry Christmas and a happy New Year’, unless you say ‘Happy Christmas and a wonderful New Year’ or some other synonym.
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Excellent point. Come to think of it, most of the cards, etc. I get from my Aussie relatives are solely Christmas cards with, perhaps, a New Years greeting written in the postscript.
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After all, as everyone knows, the twelve days of Christmas exist solely and entirely to count down to my birthday.
Your father is at our place at the moment, and he was quite pleased with some of the comments in this post… although less pleased that my church ran a “Christmas Storytelling service” for kids on Friday (TWO days before Christmas) which involved carols – apparently the earliest he’s ever sung them.
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I must admit to some influence on my thinking from my father/your grandfather!
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