It sounds like your son is definitely expressing some strong feelings, which could be from a few different things - it may be anger directly towards you because of something you did or didn't let him do (your "structured" time may be a little too structured for him), or it may be related to his frustration about things he isn't able to do yet (like talk, use the potty) or things he doesn't have control over (like people coming and going or when he gets to do things), or it could be from being overstimulated or from something else that happened earlier in the day, or it might even be an expression of feelings from something in the past (even related to birth or his prenatal time). And it may be that he doesn't know why he's mad, and that's ok. It could even be that he is simply needing your full attention and presence, and he has discovered that hitting you definitely gets your attention. If that is the case, I would suggest playing with him more. I know it can be hard being the only one with him all day, it might help to get out more and be with other people, join a playgroup etc. But if it seems to be more than simply needing attention but is an actual expression of his strong anger or frustration, what he needs is for you to really hear him and empathize with his feelings. Even though he can't talk well yet, he understands a lot, so if you say something like you're really really mad, huh? he should be able to know that you get it. Harvey Karp's happiest toddler book and video might be helpful - it's important that you use simple words and say it with feeling so he knows you really get it. You can guess about the source of his anger - you're really mad because I wouldn't let you .... (whatever it is), or you really didn't like it when ....., you wanted something or somebody else.... etc., you get the idea. At the same time of course it's important not to let him hurt you or anyone else and to help him learn other ways to express his feelings, so you may have to hold him gently but firmly while he cries, continuing to be with him lovingly and empathizing with him. He needs a "time-in" rather than a "time-out" - these are the times when he really needs your presence rather than the abandonment of a time-out. You might try showing him how to hit pillows, which you can do with him, or even, if it seems possible at the moment, turning it into a playful game of throwing pillows at each other or at the bed. The main thing is to let him know that his feelings are ok, good, and important and that you want to hear about them, while also letting him know and showing him that there are better ways to express feelings than by hurting people. After you have empathized with him enough that he calms down and feels like you "get it," you can tell him how you feel, using I-messages and not in a way that blames him - such as, I really care about your feelings, but when you hit me it hurts me and I feel sad. You can also let him know that you get mad too, especially if you can give examples he can relate to, which can help him to know that his feelings are normal. You definitely don't want to give him the impression that there is something wrong with him for feeling the way he does. I'm not sure that the "use your words" strategy would work with him yet, since he's just starting to talk. I wouldn't think that he hits you because he is in any way "sick of" you - he may be tired of being in the house all day with just you for example, and just needs a change of scenery, to go outside, explore the natural world. The idea that children save their "worst behavior" for those they feel safest with is true in a sense, but I wouldn't call it "worst behavior" but rather see it as evidence that he feels safe eough with you to express his overwhelming feelings that he doesn't know what else to do with (which is good, since it shows that you and he are well attached, although it may not seem like a good thing at the time!). And, having said all this, of course your feelings are very important too, and I applaud you for reaching out and expessing them. I hope you have someone you can talk with about your feelings, so that you can feel better about yourself and be more able to be present for him when he is upset. You can even use the feelings that come up as an opportunity to explore and heal hurts from your own past. Our children are excellent at "pushing our buttons" - bringing up our hurts from our past, so that we can deal with and heal them and be better parents. Of course it always hurts when our children lash out at us, but it may hurt even more because of something in your past. A good book is Parenting from the Inside Out, to help you explore your issues and grow as a parent. Another thought - there could also be nutritional issues related to low blood sugar, chemical sensitivities, allergic reactions - does he eat any sugar or processed foods? If so, I'd eliminate them and focus on a diet of fresh organic foods. In the case you mentioned, it could be that his blood sugar was low from having such a long nap (especially if lunch included sweets or processed foods), and he really just needed some wholesome food. Being a parent involves a lot of detective work! But it sounds like you're doing a great job and just need some more support and ideas to help you get through the hard times. Some good websites you might want to check out (with lots of free info as well as calls, email newsletters, consultations etc) include consciouslyparenting.com, connectionparenting.com, beyondconsequences.com, awareparenting.com.