OK, here's my opinion, take it for whatever you want. DO NOT expect or want your son to hold his bottle. Think about it: if he was nursing this would be a moot point. Holding him and cuddling him is what it's all about! He will only be a baby once. Do not allow him to walk around with his bottle, either. It is a meal, meals are eaten while sitting, start the habits now. Also, if you let him hold his own bottle he will start to get possesive of it and it will be that much harder to give it up. Seriously, my daughter NEVER held her own bottle, we didn't encourage it, and she had no trouble giving it up at one year. As for the sippy cup dilemma, just keep trying. He probably won't get the hang of it until he's a year old...but keep offering it so he can practice. Try the ones with the removeable valves, without the valve at first. This way it will pour into his mouth and he'll start to figure it out. Then put the valve in when he seems to know what the cup is for. If he understands then he will try to suck on it to get a drink. Also, try the cups with the built in straws...they are great, too. Good luck!