I have showed him from day one to be nice to my dog and he thinks he is, but my dog doesn't feel the same way. She is starting to hide when she sees him coming.
I showed him the correct way of petting her and he does it. But then when he wants to hug her he squeezes her so hard. Hugging in general is not wrong, squeezing her like she is a stress ball is! So I don't want to "punish" for a hug KWIM?
He also likes pointing out all her body parts and he pokes at her eyes and ears and grabs a little too rough. I try to show him "easy" but all he does is a nice (rough) hug on her and say sorry. Again, not really wrong - just rough!
My dog is old, small and has never growled at him. She just hides under the bed and I feel horrible that I rocked her world so much that she doesnt feel safe near him (except when he has cookies

)
So how can I stop him? Any ideas?
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Re: How do you teach a toddler to be gentle
We struggle with this as well (but it is with our cats). IF they let her pet them, she can be super gentle but 99% of the time she doesn't get that far because she gets so excited and screams their names when they come near and they run off.
But, what about trying with a stuffed dog that looks like your dog? Ask him to show you how he hugs doggies nice and gentle, etc.
No idea - except in our house it's not pets, it's a brother.
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This is so hard. DD now understands "gentle," but it's hit-or-miss and she's not reliable enough about it that I can let her near the dogs unsupervised. Her new favorite thing is to bop them on the nose. : (
Right now I'm just reinforcing "gentle" and praising her when she pets them nicely. Any bopping or poking and I tell her, "That hurts him/her. Let's be gentle." If she continues, she gets removed from the situation and I distract her with something else. I have nice, cushy beds set up for the dogs in my room, so if all else fails, I put them in there for some peace and quite.
I also don't allow hugging the dogs at all. Not all dogs will tolerate it, and I worry that if she thinks it's okay to hug dogs (mine would tolerate it, I'm sure), that she might try to hug a strange dog, which could be very dangerous, even if the dog is otherwise friendly. To a dog, a hug can be a threatening or aggressive gesture because you're putting your "paws" over their head.
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I rub their arms and show them gentle and it's the same way we say sorry to each other.
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We did the same thing. We used (and still use a reminders) the phrases "gentle touch" and "show me gentle" from very early on -- we'd take her hand and mimic a gentle touch with the cats, any animal in her books, her stuffed animals, each other, etc. It helped that one of our cats is very patient and didn't mind being a model for this practicing!
Lots, and lots, of repetition.
It took our cat until recently to not freak out around DD. We tell her to pet gently and demonstrate on the cat. She's become so good at it she can pat near his belly and he doesn't mind.
Before this he would run whenever he saw her. Which didn't kill him, it just meant some separation between the 2 of them.
Another thing to consider is giving the dog a "safe" place to go where your LO doesn't. It may help.