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maybe try step by step easing him over the areas where he gets afraid. You mentioned there seems to be a area that once you cross it he starts shutting down, once he gets too stressed he will not accept food so start easing him through those areas with the food as a aid and keep encouraging him with the food to make him do it on his own. maybe taking hom down and sit near a cafe and have people offer him food once he is comfortable enough. I also know there is a dog obedience class on Higston in NDG and probably also in many of the doggy parlors of Westmount where you could maybe find people to meet and greet which may encourage your puppy to become more social.
How is he with other dogs? if he dog motivated? maybe trying making dog friends and walking together to ease him through desensitization. There are also about 5 dog parks in Westmount/NDG so plenty of places to improve socialization.
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