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I would just check with your vet as you say you are going to do, but Scooby often asks to go outside and then he just takes his time and potters about for a while till he gets the urge as I say. He is so funny too because he does the turn around so many times before he settles into the job at hand, like he does those funny little circles and he might turn ten to fifteen times before he decides he has the right position. I often wonder if he gets dizzy doing that. Some times he takes longer than others to get the job done.
If you take your baby to the groomer you can ask them to check the anal glands each time as that is what my lady does for Scooby and if they need expressing she does it while he is there.
Is the food you are feeding Puddles all kibble and if so maybe a little wet food mixed in would help or maybe some raw vegetables given as treats, like carrots or beans.
If his poop is not hard and he is having trouble going just check with the vet to make sure all is ok.
 
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