As a first encounter with the world of Men, Bree is not too painful. To be sure, Tolkien weaves in plenty of uneasiness at the beginning of the chapter—the strange attitude of Harry the Gatekeeper, the unfamiliarity of the dark buildings, and the presence of Southern Men in the common room—but he manages to disarm each oddity fairly quickly with good food, good ale, and good cheer. The fact is that the hobbits have a constitutional weakness —a fondness for comfort and good cheer—and Tolkien simply exploits it.

Consider that, only the day before entering Bree, the Hobbits are lulled off their guard and lulled quite asleep by the cool shade of a harmless-looking stone. A few days before that, they are likewise lulled to sleep by a whispering stream. Several days before that, Pippin merrily bursts into loud song in the woods outside Hobbiton. (Perhaps this would not have been such a bad thing, if not for the convenient fact that it was dusk and a Black Rider was coming up behind. On a related note, it is, to all appearances, simply not a good idea to burst into song in the middle of a forest if one is a Hobbit. Frodo tries the same thing in the Old Forest, and the trees get upset and he is forced to stop.)

In the Inn at Bree, Tolkien develops the easy transition between a Hobbit’s sense of ease and of danger at least thrice, and with amusing detail. The greatest catalyst in this transformation is good food and good cheer (some may argue specifically it is good beer). Observe it happening no fewer than three times:

First, in the Hobbits’ decision to quit their room for the common room. This decision, as Tolkien tells us quite plainly, was prompted by the fact that they felt “so refreshed and encouraged” at the end of “three quarter’s of an hour’s steady going” at their supper. A chapter later in his conversation with Strider, and with the advantage of 20-20 hindsight, Frodo acknowledges this choice to have been rather foolish.

Second, in Pippin’s story-telling in the common room. He starts off with a comic account of the collapse of a roof in Michel Delving; and, when greeted by merry applause, is prompted to give an account of Bilbo’s birthday party. As Tolkien says (from Frodo’s perspective): “Pippin was evidently much enjoying the attention he was getting, and had become quite forgetful of their danger. Frodo had a sudden fear that in his present mood he might even mention the Ring.” Remember, it was Pippin who had serenaded the Black Rider earlier in the forests outside Hobbiton.

Third, in Frodo’s attempt to intervene. One would think that Frodo, at least, would be well on his guard, after having seen Pippin let down his. And, in fact, he starts off well by spouting off some nonsense to distract Pippin’s audience, and then responding quickly to a call for a song. The problem is that the course of the song itself, and the applause it arouses at the end, and (no doubt) another drink of ale, and the attempt to make the song merrier and better the second time—all of these distract Frodo from his danger, and lead to the evening’s colossal disaster. Apparently, singing in an Inn is as dangerous as singing in a Forest.

In short, Tolkien moves these particular bends in the plot along by having the Hobbits make mistakes very much in keeping with their amiable and convivial nature as Hobbits. It shows, perhaps, that he is not above exploiting the very characteristics that he makes lovable.