Dear Dr. Ada:
I have a 4, soon to be 5-year-old, the oldest of 3 kids, who has been going to the same preschool for 3 years (since he was 2).
EVERY SINGLE MORNING, without fail, no matter who takes him to school, no matter how early or late we get there, he cries for 10 minutes after we leave.
We have tried every trick we can think of, including ignoring his mild hysterics when we go. Any hope I had that he would outgrow this behavior has vanished.
I do not know what arrangements you have for your other two kids, but it seems that the boy was not ready to separate from you at age two; he needed more time with you to establish a secure sense of attachment to you.
In addition, when his younger two siblings arrived, he was probably jealous of the attention you gave to them. So try to carve out some special time to spend with him (just the two of you) to establish a stronger and more secure sense of attachment (you can call it love) between you and your first born son.
This is important for his future relationships as an adult, because a child’s feelings in the early preschool years form a template for his feelings later in life.
You can learn more about the importance of the mother-child relationship in my book, The Drama of the Mother-Child Bond: What Every Woman Should Know about Motherhood, Career and Children available on Amazon.