I don't consider it "stupid". I have been around private poker games for a very long time and it is COMMON to give small loans in situations like this. It wasn't even being nice. It is just what happens. However, the way Im handling it right now isn't how others would in this poker community. He would have already been MADE to pay. However, I am trying to be nice and just want some communication.
I posted this for two reasons, 1) to get opinions on whether this constitutes an alert and 2) to shame him into coming through with his word.