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Why does my 15 month old dog cry after he plays with his dog friend?

Buddy met a dog named Blue in his daily walks.  Now after he plays with him and we bring him home he paces, cries, and howls. Could it be that he misses him that much?  We've had to give him Benadryl in the evening so that he relax.  His vet says it is a little unusual and recommended that we take him to play with other dogs and give him Benadryl in the evening.
Blue is fixed, and our dog, Buddy is not.  Does that play into it at all?
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