Are you allowed to give the school a "trial?" IE, can you pull him out if you give a month's notice or something? If so, you can tell him that if he doesn't like it after X many days, then he doesn't have to go. (if that's an option for you.)

Has he gone to see the school yet and meet the teacher and see the room? That might help allay his trepidation.

Do you know the general schedule of the day? For example you could tell him, "You'll sing your hello song, and then paint, then clean up, then hear a story, then have circle time, and then you'll be home again!" In other words, it might help to phrase the time he'll be in school in the form of the activities.

Do you have a plan in place with the teacher if he does miss you? Do you want to be called? How do you want them to handle it?

What about the other kids in the class, does he know any of them? If not, ask the teacher/director for contacts to set up play dates before the start of school. Then it will be about having fun with friends, not about "being left."
When DD started in preschool the whole first week either my husband or I stayed in the preschool, off in a corner where she could see us but out of the way/activity until she settled in. Then we'd ask her if she was okay if we left before we'd go. We didnt leave until she was okay with it. We didnt have to do this beyond the first week.

when my 4yo started montessori preschool last fall, it was a gradual transition. first, we went in just for a visit, a few minutes of looking around. then we went in together where it was just the 2 of us and his teacher. she spent about 20 min. w/him doing an activity. then he went on a day alone for about 1 1/2 hours. he did brilliantly, so he started the next day the full time, 3 hrs./day. we went on his cues and i know that he was really ready for it since he transitioned so beautifully. if he had shown signs of needing more time, we would have done that, too.

when my 18 mo old started at the same time, he was not ready. it was a much more gradual process. we started w/15 min, then 30, etc. it took 4 or more weeks to get him acclimated.

good luck! starting school is such a big deal. i actually think i had a harder time than my kiddos. it's hard being separate from them, not knowing what they're doing, who they're interacting w/. i can't believe my first baby will be a kindergardener in just a few more weeks!!!!

My son was very, very, very hesitant to go to school. So much so that I was sure it would not last more than one day. The first school we tried was a disaster and I pulled him out after one day. (the teacher could not spell vegetable or calendar on the hand out she gave and was rude and short to the kids) The second school we just fell in love with. He was very scared and wanted to go but did not want me to leave all at the same time. This is where the teacher makes all the difference in the world I think.


Most teachers will say to make the goodbyes brief and then just let them cry and adjust. This teacher did not say that. Although she thought it might be easier if there was a time frame attached...like I have to go when the clock says such and such (or whatever works for your child) and then she stepped in and was so loving and all in his face and attached that he transitioned so incredibly well I could almost not believe it.

She also asks students to bring in pictures from home if they would like and puts them up on the wall so they can come over and see their family whenever they choose.

So, things that helped us. We went for a trial visit where we watched the class. Then we went back another day for the teacher to get to know him alone for about 15 minutes. Then on the actual day she was prepared for his separation anxiety and was very aware and with him to ease the transition. Pictures from home helped as well.

Good luck! It will be harder on you most likely.

I was really worried about my son going off to preschool. He just walked right in and never looked back! I was heartbroken as a little part of me wanted him to be sad and clingy but I'd rather deal with the heartache than have him so it worked out nicely. So he might just surprise you.

My daughter started preschool at 2 yrs 10 months (language delay, special education services) and did the same thing - walked right in and never looked back. In her second year of preschool she got really sick and had a hospital stay - after that she would just cry when we went to preschool. I'd stay with her until she calmed down and the staff was great at getting her "distracted" by involving her in fun activities.

Since you mention that they are gentle and emotion-based it is very likely that they will be able to work with him in a way that is comfortable for everyone. Can you talk to them about the methods that they use to ease hesitant kiddos into the class?

Good luck to you momma!