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I don’t have any advice for you but I do have an interesting flip side to your situation .
When both my son and daughter started preschool they pranced right off into the classroom without so much as looking back. This actually hurt my wife’s feelings a bit considering that most other kids seemed somewhat distraught at leaving their parents. Ours really didn’t seem to care about leaving us in the least.
Hang in there. Mine cried at drop off for a long time (a year). But then he didn’t want to leave at pickup every day! It got a little easier when a teacher he liked helped with the drop off and we started a drop off routine.
We are about to start with kid #2 so eager to hear if anyone has any magic solutions
We just went through the same. He was okay in about 8-10 days of school. When picking him up, spend 10 mins with him in there playing with things, getting him to show you around and engaging with the teachers and kids
Well are you primarily using pre school as a day care or to socialize your son?
Let him watch the Daniel tiger grown ups come back episode. One dad in my sons class literally opens the drops his kid off right at the door and leaves. The kid cries for less than a minute and then goes and plays like nothing happens. Talk to his care providers see what they recommend as they see this all time
Couple of weeks - hang tight. It’s not easy but will work out. Be nice and firm and go take your flight!
Our son got used to it over like 4-6 weeks (was only 1 when we started). Started slowly with just a few minutes initially and did a bit more every day. Now he loves going there.
But be aware: 2 year olds peak in stranger danger, so could take longer. We plan to start the second one also with one to avoid that (first one had to change day care with two and that was more painful)
Just transitioned my 2.5yo son and it took about a month. My contacts pretty consistently say 4 to 6 heartbreaking weeks.
For us, a week of transition and a specific goodbye ritual helped. Part of it is for them to see a specific sign and know you going to be gone. And once you leave, just go. Dont look back or hang out in front of them. You can be around the daycare, just not in their eyesight. It's hard at first, but they learn to cope. I would not do an all dya right away, would do a few hours at first and gradually increase the time. Hang in there!