I have concern about my 2.5 y.o. Bengal male cat being depressed over a kitten. Briefly explain situation: I had 2 different experiences with introducing kitten to an adult cat. First time I've decided to get a second kitten was a little over 2 years ago. While i already had 1 y.o. neutered male cat Milo I've fell in love with Bengal breed and decided to get a male bengal kitten named Chester. I followed the steps of slow introducing cats. But it didn't seem to be any problems at all as my resident older cat Milo was instantly interested in new kitten: he was sitting by the door where kitten was locked up, trying to stick his pows under to play with him. And when a few days later when we finally let them see each other it went smooth and easy and lots of fun. they became good friends. Unfortunately about 3.5 months ago Milo suddenly became very sick: he got severe blot clot and became completely paralyzed in his back paws. The vet really couldn't do anything in severe case like this and advised us to euthanize him as he was in tremendous pain at that point. It was very bad experience for us and my bengal Chester took it pretty bad: he was looking around for his friend crying for a few days. Then his personality changed: he became much less active and a lot more affectionate to me. It was strange to see as Bengal breed in general is super active and not that clingy and Chester was not an exception of his breed. So there came a decision to get another cat. About a month after Milo's death we brought home 3 m.o. Ragdoll kitten named Jax. We follow the same steps of introducing cats together, except this time it didn't really go as smooth as first time. For the whole time while kitten was looked up in separate room Chester didn't want anything to do with him. He wouldn't even go near the door just ignoring it completely. In a few days we even replace the door to the room with screen on the bottom hoping that they may sniff each other thru the screen, but it didn't work as Chester still didn't pay any attention. and when we finally took out the kitten out the room and tried to bring him closer to Chester, he was just running away like he was scared of tiny kitten. Eventually he stopped running away and learn to tolerate Jax. Chester never really show any aggression toward kitten, but mostly seems to be annoyed with him: till this day it doesn't seem that he likes him very much, and looks depressed all the time. He just sleeps most of the time instead of running around and playing like he use to. Very rarely he'd let kitten to come next to him and tolerate him for long. Kitten really likes Chester and runs to him wanting to play but most times then he comes too close Chester would just growl and run away from the kitten. The worst part it was that Chester on the top of being depressed all of the sudden got very sick: he stopped eating for a few days and about 10 days ago he started to throw up stomach bile. When i gave him some treats: he ate them but 10 min later vomited them all out. It was going on for the almost entire day. He lost almost a pound in 2 weeks I took him to the vet Monday following weekend of him being sick, but after general check up and full blood and urine tests they didn't find anything wrong with him. So my thoughts are since the vet couldn't find anything wrong with him physically, the whole sickness probably was caused by depression. They just gave me some appetite boosting pills and suggested to give him Pepcid AC. It looks like it did the trick. And since he was very dehydrated after his sickness I did the internal hydration, gave him appetite boosting pills and he's eating but just became very finicky with food, would only eat certain foods and not the others. he use to like eating can food, and now just wants to eat dry. Knowing that dry food is not too healthy I'm always to try to trick him to eat some can food mixed with a little chicken and some hight calorie gel with liquids added. I got some food sprinkles for can food that supposed to enhance the smell and taste, but didn't do the trick at all. So now it became like part time job to feed him: have to find something what he likes to eat and takes me several attempts to push a dish to him to make him eat. Then hold the kitten while he eats so he doesn't run up to him and scare Chester away from the dish. Now after over 3 months of new kitten Jax being home I still placed with the dilemma of how to pull Chester out of his depression and turn him back into healthy energetic cat that he always was. He used to love to play and run around the house, they chased each other with deceased cat Milo, and at this point I'm not sure if he would ever like Jax like he liked Milo and will ever become friends with him. BTW all my cats were neutered prior to be introduced to each other. The whole idea of getting another cat was to have a company not only for us but for our Bengal, but it seems to work just the opposite. If anybody have any ideas as of how to help my older cat in this situation it would be greatly appreciated.