Interesting. I am having some of the same problems with Thor. Thor loves people (once he's stopped barking at them), but he is very timid around other dogs.
Shyness can be genetic, so it's possible that your boy just isn't all that social.
Have you spoken with a trainer specifically about this problem? Also, it seems to me that there is a delicate balance between encouraging your dog to try new things and giving him more than he can handle. I used to try really hard to get Thor to play with other dogs, even when they were much bigger than him. Now, I push him less - I'll take him to spontaneous play groups in the park, but if he starts getting stressed, we'll leave. I also let him hang around the edges, rather than trying to really get him to interact.
Thor also goes to doggy daycare once / week, which seems to help. They have a trainer there, so I have some confidence that they know what they are doing. He's gotten much better about greeting other dogs, but I think it's going to be a long time before he really, truly plays with another dog.
Don't know if that helps at all. I'll be interested to hear what other people with shy doggies have to say.
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