Meaning and interpretation of Bilbo's "half as well" quote

In The Lord of The Rings, Bilbo says the following to his assembled guests at his eleventy first birthday party:

I don't know half of you half as well as I should like; and I like less than half of you half as well as you deserve.

What is the meaning of this quote? Is there more than one way to interpret it?

I think changing the halves into "many or some" gets past the math. More than half means many and less than half means some. And then the phrase "half as well" is "not as much" or "less than".

Both statements are expressions of regret because he is leaving and he is "immensely fond" of them.

"I don't know many of you as much as I'd like" - I wish I had time to know many you better.

"I like some of you less than you deserve" - I should have appreciated some of you more.

The language is a riddle which Bilbo enjoys and is good at as we saw in "The Hobbit" and it adds levity to his speech to hide that he is saying goodbye to everyone.

It means I don’t know some of you very well, and a few of you I ought to like better. And he said it that way because he wanted to make it difficult for his guests to quite work out what he was saying. That’s why Tolkien writes in the next line:

This was unexpected and rather difficult. There was some scattered clapping, but most of them were trying to work it out and see if it came out to a compliment.

I think Cogitative is on the right track in breaking the statement into two parts for simpler analysis, but I'm not sure that I agree with half as much of his or her interpretation half as much as I ought.

My reading of

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

is that the speaker is expressing regret that he doesn't know most of his guests a lot better than he does. The other half he either knows well enough (or better than he'd like to) already or wishes that he knew only slightly better than he already does.

As for the second part of the sentence, I think that there are two very different ways to read it. One way to interpret

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

is expansively, as being directed toward more than half of his guests—those who deserve twice the affection he actually has for them (so that he is implicitly criticizing himself for failing to esteem them as he should). According to this interpretation, the speaker is saying that more than half of his guests deserve to be liked considerably more than (specifically, twice as much as) he likes them. As for the remaining percentage of his guests, he either likes them (or dislikes them) to an appropriate degree, or he fails to like them as much as they deserve but by an amount that is less than twice his current level of affection for them.

Another way to interpret

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

is narrowly, as being directed only to the "less than half of you" in the room. According to this interpretation, the speaker feels that he likes some proportion (below one-half) of the guests assembled far less than they deserve, but the actual number of guests who fall into that category could be very small indeed; and as for the rest of the guests, this part of the speaker's sentence doesn't address them at all.

No wonder the guests were perplexed by the speaker's remark.

To break it down:

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

I really would like to know more of you, better. For example: "There's my nephew Feldic sitting in the corner - we haven't sat down to discuss our preferred beer for over 20 years! I don't even know the names of his children!"

Remember from the beginning of The Hobbit, that Bilbo was one for etiquette. He believed in saying and doing 'the right things' - an ordinary hobbit; no adventures here thank you very much.

• "and I like less than half of you half as well as you deserve"

In my opinion most of you are here for the free food and drink, and the hope to get your hands on Bilbo's 'sacks of treasure'... but I may be wrong. Please prove me wrong?

I know I'm late to the party, but...

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

He would like to have known more people than he does know.

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

Less than half of those present, he thinks deserve to be liked more than he has realized before. The rest he likes exactly as much as he thinks they deserve (most likely meant as a rather scathing insult); which is the point I think has gotten lost in previous attempts at answering this.