Spike and I have been going to the off leash park since he was five months old. There, we encounter dogs of all shapes and sizes. My theory, right from the start, was that Spike is ALWAYS going to be the smallest dog, so he might as well get used to it. He needed to learn how to behave around big dogs as much as they needed to learn how to behave around him. I decided that when we met other dogs, I would stand with my feet apart so he could have a place to "hide" if he needed to, but that I wouldn't intervene by picking him up unless I thought he was in danger.
In three years, the only problem we've had is that he got stepped on once by a bigger dog who was looking to play. He wasn't injured. I have never had to pick him up. He's met numerous Huskies, Pit Bulls, Great Danes, St. Bernards, Mastiffs, Rottweilers, and he's learned how to behave.
If you're not comfortable, then just supervise them when they're together. But they need to work it out for themselves. They need to determine who is the "pack leader". It might be your dog, even if he is smaller!
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