When & Where: I read the word guileful while reading An Abundance of Katherines by John Green (2006). The sentence is: "She had the sort of broad and guileful smile in which you couldn't help but believe -- you just wanted to make her happy so you could keep seeing it" (p. 31).
Level of Familiarity: I have definitely heard this word before, but I'm not quite sure where. I think it has something to do with being exuberant or not shy.
What it Means: www.dictionary.com defines it as "deceitfully or treacherously cunning."
Reflective Commentary: This makes sense because the main character is describing a country girl from Tennessee, who's got a bit of mystique surrounding her. She seems like a plain and simple girl, but it turns out that she is quite mischievous and the other characters find this out immediately after. I can't see myself ever using this word; however, I do think it's important to know because it adds to the description of the character and can be used to describe a lot of characters in literature. If I was teaching a novel to the class I would want to teach them about descriptive/characterization words, and I believe this would be a useful one.