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My question is how can we assure Chester that we're here for him too?
Your puppy is cute. It will take a lot of hard work to make chester feel secure. Just try to remember that when he is scared or shows signs of anxiety to try not to reinforce his actions with cutesy words or baby talk. our first impulse is to cuddle and soothe but that actually aids the anxiety and behavior. Just sit next to him and let him come to you. also, try to take his mind off of it by redirecting his attention. I had a cocker spaniel who was afraid of everything but she had the sweetest disposition of any dog I had ever had. She also had epilepsy and liver issues. She passed last year and I miss her so very much. but in her last year, she had finally begun to trust me and would come to me when she was anxious and I would just love on her without saying anything. Good luck with your "baby".