Well, this breaks my heart--

Last week, after I'd said goodbye to Lefty for the day, I was talking to a neighbor when I thought I heard howling coming from the house. I heard it again the other day, but when I moved closer to the house it stopped. Today I confirmed that it is indeed Lefty.

He shows no signs of unhappiness when I leave. I give him a rawhide and he trots around with that while I gather my things. When I say goodbye to him he seems fine.

I've thought more about getting another dog to keep him company, but I've decided it would probably hurt him more than help him. He seems frightened of most dogs, and is so needy that I think he would hate having any competition for our attention. The trainer brought up dog Prozac or similar drugs, and I'm beginning to wonder if that's not something I should look into. Any of you have any experience with this stuff? I'm not sure what else I can do. He just doesn't seem happy, and I feel bad for him.