Update from yesterday. It does appear now that the information given at Reddit is likely credible, and from the young lady that Timmy had a failed courtship with. Some did notice some months ago that Timmy Rodrigues posted a review of a pawn shop talking of buying a ring, and wondered what was going on.
Perhaps there was a courtship that was completely unapproved of by Mama Jill, and shut down the second she discovered it?
This being the lady he was courting would make all of this make some sense. Right down to knowing so much intimate about the family.
File this under when Quiverfull does not work. Too many children to properly care for them all.
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