Hi 3. B.,
If I could offer some reflection, it sounds like you are doing a lot of “telling” him things you want to see happen. He needs to have some consequences, immediately, for what he does, when he does them, so that he will stop. The consequences DON”T HAVE TO BE time outs. I think that time-outs can be an alternative that is sometimes effective. But sometimes, depending on when and how they are used/discussed etc. they can also be completely ineffectual.
For example - the parent who told her daughter “If you push at the table, we will have to move you so you can’t do that…” was telling daughter what to expect if she chose to do that action again. Daughter tried, parent followed through, and after about 2 tries, daughter stopped doing it.
So, in your case, if time outs aren’t working, you need to find some kind of leverage - some alternative that seems reasonable to the child and also a choice that is less desireable than sitting at the table with you, his parent whom he loves and underneath it all, wants to be close to.
Another thing you can do is try to make it really fun to do as you ask. Maybe offer a special meal-time toy (car? - have you seen those spoon/forks that have fire engines for handles? ) Something that makes him feel special and a Big Boy for sitting at the table. You can show it to him, and discuss how exciting it is, and then set the standard for what you want to see him doing in order for him to eat with the special toy/utensil/plate whatever. ie. “You can have this toy if you follow our rules for eating politely at the table like a gentleman. Can you tell me what the rules are that we expect? We keep our feet calm below our seat. We put food in our mouth and chew with our mouth closed. We treat our plates and cups and forks and spoons with respect so they don’t get bonked on people or each other. We use two hands to drink with our cup all by ourself so we don’t spill. etc.
Notice here that the word “no” is NOT USED in the rules. It tells your boy what you REALLY want to see, so frames it positively. You can even mention how happy it makes you when see him following good behavior at the table.
Thanks for letting me write this, it helped me to process how some of my own behavior (giving too many chances) may be contributing to my own son not listening to me well. I have a 4 year old who does observe good table manners (praise g*d!) but he has moved on to test me in other ways where I guess I am more fuzzy on what the rules are myself so I don't follow through well enough myself...Good luck. I can tell you are a really caring parent who wants to do the best by your child. Just remember that at this stage in their life they are looking to push and test the boundaries to see what flies and what doesn’t.
Oh, and PS. I just thought of it - the other thing I was thinking to say is that if the boy's feet are constantly positioned so that he can easily kick the table maybe that is his physical (because boys are a bit less verbal and more physical at this age than girls) way of telling you that his feet are bumping the table. Maybe it is time to move him into a real chair where he has to dangle them down and stretch his body up so that his head can come above the table to eat. I never had a high chair in our house for either child (I have 2) and I think that sometimes that makes them pay more attention when they have to be in charge of their own bodies not falling out of the chair.
Finally, I know it may be easy to feel like NOTHING IS WORKING, but do try to just take each situation as a puzzle not as something that reflects back negatively on your child's overall character. I'm with you, I happen to think most kids are waaay smarter than their parents usually give them credit for. I have found the best behavior comes from my kids when I treat them like they are a real person who may have needs and wants different than mine that they may not be able to verbalize well. If you child reallly realllly reallly likes to kick, give him an opportunity to do that elsewhere, not at the table - like a wall? or a special kicking pillow? A soccer ball!!! :) Good luck.