I think I mentioned before that I find Max oddly compelling as a character in Rune Factory 2. In fact, were my 1st Generation character a girl, I would court him instantly. His personality is so ingenuous. His arrogance, rather than being infuriating, is rather charming for some reason. Perhaps I cannot justify or explain it fully, but I like Max immensely. (Could it be nothing more profound than an attraction to guys with long blonde hair? Could be, I suppose.)
The only time Max slightly disturbed me was when he offered my 2nd Generation character a kiss on the cheek as a reward. I am quite certain he was offering in a purely avuncular manner, but it smacked a little of inappropriate behaviour by an adult towards a child. At the age of 9, a kiss on the cheek by an uncle is natural... I suppose it disturbed me mainly because I didn't feel like a 9 year old child and actually would have liked that kiss. (Meanwhile, to my fury, my character automatically rejected it with utter disdain and repugnance.)
In any event, there are a number of Request Events in Rune Factory 2 that involve deceit of one kind or another and one of them involves Max. Here are three of them. The first features Max, and his desire to 'prove' himself an action hero. The second and third are 'Heart Events', although Alicia's Request typically requires that you romance ANOTHER woman in order to prove her fortunetelling abilities.