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Toby is almost too well behaved and I'm not sure if it's out of boredom or contentment.

I'm away for 10 hours a day. When I get home there is no sign of any mischief while I was gone. We play a bunch, maybe a walk outside, dinner, TV time for me and random play in the evening. He doesn't initiate play with me much, but is always ready when I start it. He'll follow me around as I do house work or stuff, and sometimes just sits and watches. He's not very vocal or demanding, and very often comes to just sit in my lap, or bring a toy with him and drop it in my lap and lay down. At night he'll lay in bed wither a couple feet away or against my legs. Whether I wake up at 5 am or 8 am, he never fusses and just sits or lays there waiting for me to get up, always ready for his morning petting session.

I'm really enjoying this laid back kitty (really, at 6 months old I thought he should be a monster).

If you review the attributes I mentioned, I am wondering if he's content, or bored. If he's really bored I'd consider bringing home a shelter kitty of one from a foster home. If he's content then I am happy leaving it just the 2 of us and not having to worry about the "kitty 500" at 3 in the morning. Or the flying across the tables kicking everything everywhere. If he is bored, he hasn't been getting in to any trouble looking for attention.

I guess I'm looking for what's best for him and for me.

Oh, I just got back from a small private pet store. The manager had her cat there. I let Toby out of his carrier (on a leash) and he showed little interest in the other cat which was only a foot away, but rather was eager to play with the brand new feather wand that the manager brought out.
 

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Toby sounds like the perfectly-behaved contented cat. Lucky you! I wouldn't worry....if he was bored or depressed he'd be doing a lot more sleeping, and likely showing little interest in your activities. He may become more mischievous and bratty when he's 8-9 mos. tho.
 

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Toby sounds like the perfectly-behaved contented cat. Lucky you! I wouldn't worry....if he was bored or depressed he'd be doing a lot more sleeping, and likely showing little interest in your activities.
That's what I was thinking. He's super playful with me. Even after our playtime is over (I do have things to do also) he's still very happy going on his way playing with his stuffed toys, kicking them and dragging them around the house.

Yes, I think I got lucky.
 

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He's content. Believe me, if he were bored you'd see a lot of destruction going on!!

Milky is usually very well behaved while we're at work or gone out. When we come back, that's when the destruction starts! He expects us to play with him nonstop until bedtime, but that's just not ok because we have other things to do while at home sometimes. We play when we get home from work, then again after dinner and before bedtime, but it just seems not enough for him. He gets bored when we stop, so he finds naughty things to do, like jump behind the TV cabinet when we're not looking and get tangled in the cables or bang his head off the corner of the TV, or swat everything clear off the tables, bite our shoes... the list is endless!! It's as if he purposely did those things to test your patience! He tries endlessly to do those things once we get him away from those places... It can be a real nightmare sometimes!

But when he's good, he's a little darling and you can't help but forgive all that he's done! :)
 
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