I’ll be honest- when I read The Hobbit and The Lord of the Rings the first time, I didn’t really know what was going on.  The story was just so dense, and I had a difficult time keeping track of the characters.  After The Lord of the Rings movie trilogy came out, I picked the books back up and enjoyed them a lot more.  J.R.R. Tolkien’s writing can be a bit confusing.

Take, for example, the above statement made by Bilbo at his party in The Fellowship of the Ring: “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.”  Bilbo’s guests didn’t know if it was a compliment or an insult.

So what did Bilbo mean?

First, it’s important to know how many guests were addressed by this statement.  The party was to celebrate Bilbo’s 111th birthday and Frodo’s 33rd birthday.  As Bilbo explains at his party, he decided to invite 144 guests to mark the number of his and Frodo’s combined ages.

“I don’t know half of you half as well as I should like…”  Don’t get tripped up by that second “half” thrown in there.  I don’t know that you can really quantify how well you know someone, so the second “half” is really just an extra des c r i p tive word.  If we take the first instance of “half” to mean quite literally half, Bilbo is directing this comment to 72 of his 144 guests.  It basically means that he doesn’t know 72 guests as well as he would like.  Or, on the flip side, he does know 72 guests as much as he would like.

“… and I like less than half of you half as well as you deserve.”  Once again, taken literally, this statement is directed to 1 to 71 (less than half) of his 144 guests.  This is Bilbo admitting that he does not like this portion of guests as much as he should.  (Once again, I don’t know how you quantify that, but I suppose these guests should deserve to be liked twice as much as they were by Bilbo.)  On the other hand, Bilbo likes more than half of his guests (73 to 143, depending on how many are in the “less than half”) as much as he should.

Basically, Bilbo is stating that he regrets not knowing many of his guests as well as he should, and that some number of guests are more likable than he gives them credit.  This is all just a really convoluted way of Bilbo realizing that his eccentric habits (compared to “respectable” hobbits who don’t seek out adventure) and reclusiveness have prevented him from bonding with other hobbits.

At this point, you may realize that some of the guests are left out of this tricky statement entirely.  Even if we are to assume that the first half (72) and the second less-than-half (1 to 71) don’t overlap, that leaves at least 1 guest out of the 144 that Bilbo does know as much as he wants to and like just as much as he should.  You could interpret this as a compliment- that he’s close to at least one guest and likes them as a close friend or family member.

I prefer the alternate idea, which is that there’s at least one guest who Bilbo doesn’t like at all.  In this case, Bilbo would feel like he knows the guest (or guests) just enough to know that he doesn’t want to get to know them better and that they are deserving of his dislike.

In other words, Bilbo really, truly dislikes Otho and Lobelia Sackville-Baggins for trying to take over his home while he was gone during his adventures during The Hobbit.