Wing man!

I think it's funny that "Gil" is using Jack as a wing man to get his mother. But in actuality Jack is using Gil to get free stuff that he's wanted like this bike. I also think that Judd is scared of Gil because  Judd does what ever Gil tells him to do. But this is a normal approach on a single mother. All you have to do is make close friends with the kid and you will get the mother. It's like walking your dog to pick up women it works most of the time.