you know that if he wants someone to commiserate about fae contracts - Gil is there to talk about it. I am also happy to come up with a plot that Gil somehow came across the Fae that Ethan is hunting. After all, Gil did rob a lot of nobles back over there. :)
Dean would just be a more friendly connection, and be a bit confused if he finds out Ethan's true age, and then take copious notes about the supernatural stuff.