When introducing a new cat into the house it usually works best to bring in one of the opposite sex. Also consider getting a cat that isn't strictly a kitten.
I had Charlemagne (a male) by himself for about 3 years when I got Regina. She was a runt of a kitten but very feisty. He was very good with her most of the time. Check with sites like CatAge or Catster for more info on this. I could probably go on for half a page with what I've heard and what I've done but I won't. Or call the local shelters and see what they say. Talk to your vet.
Good luck. And welcome back.

I asked my boss (I'm a vet tech, boss is a vet), she just said it depends on the cat lol... We were thinking a kitten because Jonathan is a special needs child, and the adult cats that he's been around (other than Bob) are mostly afraid of him due to his behavior (he is loud, even for a 5-year-old, along with other things). We got Bob as a kitten so he's used to Jonathan and they play non-stop. Otherwise I would get an adult cat before considering a kitten.

Ah I see. Yeah a kitten might be a good choice unless you can find a tolerant young adult. They're out there. It does depend on the personality of the cat. Some are more tolerant of newcomers than others. I'd LOVE to have a kitten in the house but I doubt Zenobia would take it well. She's VERY territorial and plays rough and I'm afraid she'd hurt a kitten either accidently or on purpose. Ashera would be OK with it after the usual 2 week acclimation period. Unless I found another Regina (who had Charlemagne completely flummoxed as a kitten. He'd walk up to her and she'd flop over on her back with the claws in the air and the ears back.He NEVER figured out how to handle that.) I wouldn't dare bring a kitten into the house.
You know Bob better than anyone else. How does he react to cats in the yard?

we got aboy kiity as afriend for my little kitty girl. They aget along well sometimes. I thik an animal of the opposite sex would be a good bet because another male might be percieved as a threat even if your current one is fixed.

I agree with Melinda. A lot depends on the personality of the new cat and the residient cat; sometimes you can't tell what a kittens ultimate personality is going to be when it's an adult. I don't think it would matter if it's another male--I think the trouble with males starts when they reach sexual maturity and if the kitty is neutered that shouldn't make a difference. Among my 12 there are a few that would probably get along with any cat and a few that barely get along with the others. But there's never any out & out fights because I introduced each new cat slowly--every new kitty gets quarantined in the kitty room for a few weeks or however long it takes for the new kitty to acclimate. The ones that don't get along just avoid each other in my house. But I know you are looking for a companion for your older kitty--probably a kitten would be a good choice if your older cat gets along well in general with other cats. But you never know....getting cats is like " a box of chocolates"....sometimes you never know what you're going to get :)

All my boys (6 of them)get along and play together. My girls (3 of them) tend to not want to play with the boys and are more hissy.

My friend and I have cats around the same age. Last Summer, I tried bringing her cat Harley to my trailer because she was away and it was so hot. Harley hid the whole time. My Joy hissed and growled and did NOT like him in her territory.

Several months later I got a kitten from a cousin (who turned out to be sickly and died 2 days later), and Joy hissed and growled at him even more. I was hoping to give her a playmate, but she likes her space.