[The Squatter of Amon Rûdh]

I missed this thread the first time round, so I'm self-indulgently resurrecting it so that I can have my say.

Bilbo is saying a number of things in his convoluted statement, most of them pleasant and some of them less so. I'll take it all point by point to simplify things.

I don't know half of you half as well as I should like

Or as has been pointed out above: "I should like to know half of you twice as well as I do."

and I like less than half of you half as well as you deserve.

Or "...and less than half of you deserve me to like them twice as much."

What everyone's missed here is that Bilbo divides the hobbits into three: those he doesn't know as well as he would like (about half of those present), those he does know, but doesn't like as much as they deserve (just under half of those present), and those he both knows as much as he would like and likes as much as they deserve (some undisclosed very small number of those present). The last group is implied by exclusion, and is the most ambiguous of the three. Bilbo's showing very unhobbitlike cleverness, because it's up to each individual to decide where they belong, and the last group could include both Frodo and the Sackville-Bagginses.

Bilbo could have said: "Half of you I don't know very well, most of the others I like less than I should and I think of everyone else as they deserve." He could also have said: "I'd like to know half of you twice as well, I should like nearly half of you twice as much as I do, and the rest have no cause to complain." The point is that that's a very ambivalent comment however you dress it up, and he's deliberately obfuscated his meaning to buy himself time while his audience works it out. Probably some of them never did.

Tolkien had to do quite a lot of public speaking in his time, since a professor's job is to profess: in fact he delivered far more lectures than his contract required. This little aside makes me wonder whether he was in the habit of making comments deliberately calculated to go over the heads of his audience, and with his audiences those would have to be very clever comments indeed. He was certainly no stranger to the skullduggery of faculty politics, which is abundantly clear when he shows great councils in session. Bilbo isn't the only character who likes ambiguity either: notice that Gandalf is also good at quiet criticism (witness his smoke rings during his argument with Saruman in Unfinished Tales), and Tolkien genuinely seems to like it when people are rude without being obvious about it. The question of insults is also very evident in Lobelia's attack on Frodo ("you're no Baggins... you're a Brandybuck"), which is meant as an insult, but which Merry claims is a compliment, before reversing that into a playful insult by implying that it couldn't possibly be true. Such is the stuff of social interaction, which is why some people become hermits.