One thing you might want to start working on (and it will take a lot of work) that might help with the chaos a little is to teach him he cannot interupt while adults are talking. If he has something he wants then he should wait until after your discussion with the sitter. To help that along you may want to bring in the snack and drink and give it to him while you talk.
Em was so bad for interupting when she was about 5 or 6 because she wanted what she wanted right now. We started working on it and it took a bit of time but she learned. I made it to where if she interupted she would not get what she was wanting until she could ask politely without interupting. Believe me it took some will-power because sometimes it's just easier to give in but it worked.
I agree with Diane, you might want to discuss what you are going to do that evening before you drop him off, if that is possible, and then maybe let your sitter know so that she can remind him during the day. If it is something that is fun that he wants to do let him know that if he interupts you when you pick him up then you won't go.
Just a suggestionl.
It seems as though our summer 'chaos' has came to a halt too soon for our ds. Now when I show up to pick him up from the sitter's in the afternoon, he starts in with "I'm hungry, I'm thirsty, I want a snack and I want to do something tonight that's fun..." And he just hangs on me...This is all going on while my three year old is wanting hugs, too. AND while the sitter (also my sister in law) is trying to give me info...
Lately, I just feel like I'm seriously walking in a cloud and in a daze. I was sick with the flu all weekend (who gets the flu in the summer?? ) and so I just feel emotionally, mentally and physically drained. I am completely dreading picking up my ds in an hour. Do you all have any advice for me on how to 1. get some organization to my pick up and 2. clear him of doing this to me at all??
I'm tired and I greatly appreciate any of you taking time out of your busy days to help me!! 
yay!!you could have a snack and drink in the car................
as far as evening activities, maybe discussing ahead how the evening is going to go he'll accept things more readily. Probably wont stop asking, but you can at least say, we talked about this (then he'll say her forgot
).
They may just be missing Mommy if you've been out of sorts with the flu.
I hope you feel better
Diane, you are right! He will say "I forgot" he says that about EVERYTHING!!
Good grief! ha ha
I left out an important thing about the snack and drink, when 3:00 rolls around-the sitter gives him a snack and drink. So, when I pick him up at 4:00 he should be satisfied and I need him to eat at supper-so I don't give him more. He hates fruit because I had considered bringing him an 'appetizer', if you will, but other than fruit-it's hard to think of something that would compliment dinner! Does that make sense?
Jamie, you're right about the interruptions. He has backslided on that, he used to be very good about it. He practically pulls and tugs at my clothes to get my attention. And the whole time my SIL (their sitter) is filling me in on the week or the day and I'm just not getting it all. I'm undiagnosed ADD, I believe, and so I don't hear half of what she tells me...then later I miss something because of that conversation I never 'got'. So, I'll try that over....
It seems small, but I literally just dread that 15 to 30 minutes (thank God that's my biggest problem, I do realize that, you all!
).
Diane, you're also right that they may need some quality time with me and we're going to have a movie night tonight so maybe that will ease their little hearts.
Thanks!!