so, not to dwell on this too much, but I think I have come up with a good analogy for why this is so weird to me
Brian Kelly is to being interested in a players family as Eric Cartman is to being nice... they just can't quite figure it out and it ends up being more creepy than genuine
http://www.southparkstudios.com/clips/154200/cartman-beats-up-jimmy
Advisor: the best thing isn't to act like you are interested in a player's family, the best thing is to be genuinely interested
Brian Kelly: okay, how do you act genuinely interested?
Advisor: I give up, why don't you just break down film of his younger brother?
Brian Kelly: that's a great idea! I will wear a nice sweater too!