When I had Taz and he was at his "healthiest" I had to feed him only twice a day, not free feed. But as the end came near and he was losing so much weight I left food out for him and began feeding him wet food (I HATED wet food, it made me gag to serve it). I did anything to get him to gain weight, quite the opposite of his early years.
With Paizly I can free feed her and she doesn't over eat. Now, little Jaxter is a PIG! He has his kitten food in his room but he will eat all of Paizly's adult food. However, he has stopped doing this as much lately (thank goodness). Oh, and since I began Taz on the wet food, I still give Paizly and Jax 1/8 of a can of wet each morning (only on work days though).
When I had to feed Taz only twice a day I'd give him only the "allowed" amount in the morning and then again at night. Eventually he would still have some left in the bowl at the night feeding. On weekends he'd meow his head off like I was starving him to death, but I wouldn't give in. Ok, I did sometimes with a treat.But not a lot!!
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