Clearly, something has gone wrong - Tim was finally talking, but now there's dead space and it's back to "man this was a boring book".
Again, Jen is being too influenced by her own understanding of the text and is looking for certain interests and answers. She is also probably getting rather frustrated with Tim by now. The result is that she misses an important part of Tim's statement. Tim says that the native woman is cool, but he clarifies her "coolness" through a comparison. He joins the native woman with the other natives and says, at essence, that the natives are more appealing than the white "pilgrims." This opinion could be pressed further.
Though Jen missed the mark at this point, the session is not yet a bust. Jen has gotten Tim to start talking, and as long as a writer is talking, there is hope for a successful tutorial.