You sound like me/my baby too and I just recently had a request on here about a 10 1/2 mo. old waking for bottle, but I gotta say my opinions about some of the below responses (sorry!!). I would not take away a nap. I believe that they let us know what they need and we should give it to them (I mean the word "need") like naps, bottles, etc.) I watch my baby's cues and if she rubs her eyes and is cranky no matter what I try to do, then I know it's time for a nap. Sometimes lately she's only had one in the afternoon, but maybe because she slept longer at night or didn't do much - if we were driving around in the car, etc. So, sometimes they just may not need 2 naps, but I think at his age (I know mine did and still does) he needs 2 naps still and the times are perfect. I don't believe in not letting them nap past a certain time. And if they become overtired, then it's hard to get them to sleep (for me anyway). So, I find if there's a good balance of eating/playing/napping, then bedtime at night is better. If he's teething, let it go and don't act like it's a normal thing where he's just trying to get attention or whatever. He needs to be soothed and whether that's rocking or a bottle - try to make him comfortable. I believe these things will pass and to just take each day as it comes and take the best care we can because they grow so fast. I never let mine really cry it out and she's transitioned from a long time ago of sleeping propped up on us (she has GERD really bad) to napping on her own to sleeping in her bed on her own and she's so comfortable knowing I respond to her so quick, that I think that helps. I let her fuss and fall asleep on her own so she can self soothe, but I think if they're really crying for us, they're trying to tell us they need something (at least if you know he's teething or something). I'm too much of a softie and may regret things one day, but hopefully it'll all work out. Good luck to you too!!