I see this whole chapter as a test. Maybe the characters don't even actively know it, but it's totally a test.
And that was a real dick move on Bob's part. But Jessica is so vapid - she couldn't even think of an actual important something to say to him. I'd like to know what else he said to her back at her hotel room.
Author's response
Oh you always see beyond the words. That's great. Hey here's an idea. Why don't you write a short story telling just what happened when he got to Jessica's room? You know some of what she said to him. I'd love to have you do that if you have the time and want to.
Oh crap I forget something. There is something else Jessica tells him that he tells Willow in the next chapter. So if you do want to write something for this just send me an e-mail (my contact info is on my page) and I'll tell you what it is.