I agree that it's probably just that the parents aren't making him put his own shoes on. They are doing it for him, so he makes his little pathetic attempt when you tell him to do so himself, then he fusses and expects you to do the work for him.
I would tell everyone to put their shoes on. When it's time to walk out of the door, tell him to carry his shoes outside (so he can put them on while outside). If he refuses to carry them, then I would pick up his shoes, then I would have him go outside and make him sit on the porch not being allowed to play until he gets his shoes on himself. That way, the other children are not losing outdoor time because of him, but he will see the other kids playing and having fun while he isn't allowed to do so until he puts his shoes on. I would continuously tell him, "They put their shoes on, so they can go play. As soon as you put your shoes on, you can go play. Now put your shoes on so you can go play." It will be more work on you. I'm sure he'll throw a fit, try to run off the porch to play barefoot, etc. But it will show him that he won't get away with not doing what is expected of him. And that since the other children did do what was expected of them, they can have their 'reward' of going outside to play.
I would tell everyone to put their shoes on. When it's time to walk out of the door, tell him to carry his shoes outside (so he can put them on while outside). If he refuses to carry them, then I would pick up his shoes, then I would have him go outside and make him sit on the porch not being allowed to play until he gets his shoes on himself. That way, the other children are not losing outdoor time because of him, but he will see the other kids playing and having fun while he isn't allowed to do so until he puts his shoes on. I would continuously tell him, "They put their shoes on, so they can go play. As soon as you put your shoes on, you can go play. Now put your shoes on so you can go play." It will be more work on you. I'm sure he'll throw a fit, try to run off the porch to play barefoot, etc. But it will show him that he won't get away with not doing what is expected of him. And that since the other children did do what was expected of them, they can have their 'reward' of going outside to play.
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