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Sounds just like my Toby. Purebred, came to me just under a year, very timid of men, crate trained. Time, time and more time is what it takes!! We always left his crate door open and he could go to his safe place anytime he felt intimidated. As time went on, it just got better and better. He is still a little shy with strange men (strangers, not weird!!lol), but I don't mind that. He doesn't jump up on people or anything which I always thought was a nice side-effect of that timidness!

A couple of things that worked for us. Opening his crate door and letting him decide when to come out. DH gave food, treats, toys, etc. to give him a positive view of men. DH would take him outside more, so he started to associate good things with the man of the house.

Hope that helps!
 
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