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How to know if your cat is overweight?
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As people have said ribs are a good indicator, as well as the back hips and shoulder blades peaking out to form a visible "waist" as well alongside ribs being easily visualized (spinal segments being visual as well is bad). For the food anxiety I'd recommend play stimulation and likely catnip and/or catgrass.
His large pouch makes it tricky to use his back hips as an indicator, it sort of pulls the skin taut in that area. Even when he was quite obviously overweight he had a visible waist. But I checked his ribs and he definitely still has a solid layer of fat.
It never occured to me that boredom might be a factor. It's gotten colder here recently so he hasn't been spending much time in his catio. I do play with him at least once a day, but he's almost 14 years old and he's not as into it anymore. I'll get him some cat grass.
Thanks