Anyone have any experience with a dog that experiences separation anxiety when separated from another dog?

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I'm bummed out by my discovery today. I had suspected it for some time, but I hadn't had the chance to fully test it until today. Apologies for the length; I just want to be thorough.

Some background: I adopted a four-month-old puppy back in late April of this year. His name is Zinfandel, Zinny for short. He is my heart. He was terrified of everything — clearly, he missed his key socialization period, and on top of that, judging by how he reacts to certain people and their movement, he may have been abused.

Pinot, my older dog of seven years, is perfectly well-behaved. Used to be reactive, but I've worked with her to a point that she's more than manageable on a leash. I could not have been luckier than to have adopted her years back.

Since April, I've let Zinny and Pinot spend all their time together. This may have been my mistake, but I thought that because Zinny was so frightened of everything that Pinot could really give him confidence.

Over the past few months, the confidence came, and he's blossomed beautifully. He's made leaps and bounds in his training, and he's grown to be less afraid of new things than he was before. He's overcome so much in just six months — introducing almost anything new has been a hurdle.

My husband and I usually walk the dogs together. Zinny's learning how to walk on a loose leash fairly well, and Pinot's perfect as always. In recent weeks, my husband's been busy, so I've walked the dogs one at a time a couple nights each week. I've discovered that Zinny is fine going out with me by himself. However, if I leave him at home and take Pinot out, my husband says that he whines and whines and waits anxiously by the door. Just as a note, he will eat his dinner from a puzzle toy of some sort– he's just kind of whiny while doing it.

I wasn't sure if it was me being gone that upset him or if it was Pinot, so the next evening, I had my husband take Pinot out. I witnessed the exact same behavior with Zinny as my husband did. Able to eat, able to play, but in a very distracted way, consistently whining and looking towards the front door. We still weren't sure if he was upset that Pinot was gone or if he was upset that Pinot was outside enjoying her walk, while he had to stay at home.

Since then, I've been experimenting a little more. Anytime I separate them with the baby gate for short periods of time while I'm at home, Zinny is fine. He may be a little whiny to start with, especially if I'm training Pinot, but he waits by the gate and quiets down after a few minutes.

I thought that perhaps as long as he knew that Pinot was there, he might be okay. So today, I separated them before I left for work — in less than three hours, my husband would be home for his lunch break, so I gave them each a frozen kong filled with peanut butter, kibble, and carrots, and left them. Zinny had zero issues with me leaving. He carried his kong off and went to lick away.

When my husband came home for lunch, he said Zinny was frantic, jumping at the baby gate and whining in a panic. The puppy had gotten in my Costco-sized back of flour, and there was flour everywhere. When he was let out to join my husband and Pinot, Zinny whined frantically for a few moments longer, wanting pets and cuddles, and settled down after a couple of minutes. Nothing else was damaged, and there were no potty accidents. I am unsure if he was barking, but I will be getting a camera to find out.

As a note, Zinny's normally not a destructive puppy. We give him adequate exercise/structured play and plenty of mental stimulation/training. When he's left alone with Pinot, we have no problems with behavioral issues, just two very excited dogs when we come home.

I'm heartbroken that he was so panicked during this time, and I'm determined to do anything I can to help. While leaving him with Pinot allays the symptoms, it's clearly not the solution. I want to teach Zinny to be comfortable being by himself because it's a life skill that he needs. I feel awful that I had not addressed this before, but amidst all of the other training and counter-conditioning I had to do with his fearfulness, I simply hadn't thought of it.

My main issue is that I've done quite a bit of searching for resources that address this, but most, if not all, separation anxiety books and articles focus on dog-human anxiety. I've yet to find anything on dog-dog anxiety, unless it's buried deep in the books.

I've already ordered "Treating Separation Anxiety in Dogs" by Malena Demartini-Price and "I'll be Home Soon: How to Prevent and Treat Separation Anxiety" by Patricia McConnell. I'm hoping to glean some insight, even if these books address primarily dog-human separation anxiety. I have a good idea of how to work through protocols — I just don't know if there are any nuances that I should be aware of when it comes to dog-dog separation anxiety. I think Zinny's anxiety is pretty mild compared to other cases I've heard/read about, but I really have no basis to my nonprofessional diagnosis.

I welcome any advice, resources, or anecdotes that might help or give me a better understanding of separation anxiety, especially between two dogs. Thank you so much in advance to anyone who responds! I appreciate this sub immensely!

tl;dr: I think my puppy has separation anxiety when I separate him from my adult dog. Help?

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