We still have 1.5 years until Jacob enters Kindergarten, so maybe this worrying is a bit premature, but I would still like everyone's opinions.

Jacob has grown into a very shy little boy. He does not like being in big social situations unless one of us is with him, either Mommy, Daddy or his sister Natalie.

He and Natalie are very close, almost like twins, although they are 11 months apart. Jacob has no memory of his life before Natalie was in the picture. Natalie is very outgoing and friendly, and I notice that Jacob relies on Natalie a lot of the time to be the ice-breaker in social situations (such as parties, playgrounds, daycare, etc.) It works fine I suppose, except that I worry for when Jacob has to go to kindergarten, because he and Natalie won't be in the same grade and he will have to learn how to function without her.

There are a lot of activities that I think Jacob would really enjoy. There is a summer camp called "Camp Little Engineers" in our area for 4-5 year olds, it's a half day camp every day for one week where you drop the kids off and pick them up a few hours later. I know he would love the kinds of things they do, they focus on building things and circuitry and how electricity works, etc. He would love it. But when I explained to him what the camp would be like (Mommy, Daddy and Natalie wouldn't be going with you) he instantly said he didn't want to do it, and he doesn't care what kinds of activities there are - unless one of the three of us is going to stay with him, he doesn't want to do it.

It also is an issue at times at home because Natalie is much more independent minded and prefers to play alone sometimes, and Jacob will literally never leave her alone to be by herself. He hates to be alone and doesn't want her to ever do anything on her own without him. It is the cause of many fights between them. I usually have to give Jacob something to do with me or with H to keep him occupied so that she can have some space.

My goal with getting him involved in some kind of activity was three-fold. I think he needs help cultivating his attention span and discipline to be able to sit in a classroom when he gets to school and focus on the teacher. Kindergarten in our area is a full-day program with no half-day options and to me that is pretty intimidating. I know he has 1.5 years before he will get there so I am hoping we will see some major leaps in his maturity during that time, but I still feel like HE would be more comfortable in the long run if we prepared him first because that is how his personality is, he likes to be prepared and know how things are going to go, and dislikes surprises or unknown situations.

I think he would genuinely enjoy some of the activities that are around and available to him and I would like to see him make some friends outside of the family and outside of Natalie, so that they can begin cultivating their own lives as individuals (mostly him, so that she can have a bit of a break...she asks me sometimes if she can do things without him).

Also, I want to see him build up his confidence and not be so fearful of new situations or so painfully shy and worried about being on his own.

H and I both work full time and he goes to daycare while we work. We have not done preschool for him because 1) we couldn't justify the cost and 2) haven't found a program that I actually liked and 3) I honestly worried he'd be bored by the material because he is well ahead of the game in terms of academics like math, reading, writing, etc. Daycare is at MIL's house, she is a licensed in-home provider and has other kids in addition to Jacob and Natalie, so they do get socialization there...but again, Natalie is there with him so he still leans on her a lot.

What do you all think? I don't know what the right thing to do is. Do I try to convince him to enroll in some kind of activity (and force him to go even if he says he doesn't want to)? We talk with him frequently about his fears and his worries and it doesn't seem to really help or change his mind. I know he's too little to understand that sometimes we all do things that are scary to us at first but later we enjoy them.

H and I are huge softies when it comes to this sort of thing. We were both very shy as kids and remember how scary it was to go to school, but neither of us had siblings close in age so we were used to being alone and doing things on our own at the same time. I just want to do whatever I can to make him the most comfortable when that day comes.