My sweet Ben.

He recently started preschool. Finally, he can join his siblings in the chaotic morning rush and the evening chatter of “what happened at school today?” As the first day of school neared, he talked about being scared – but then two minutes later he’d talk about feeling excited. He’s seen enough pick-ups and drop-offs to know that his grown ups will always come back, so his first day jitters were more about facing the unknown than saying goodbye to Mommy and Dad.

He was so cute and brave on the first day – he didn’t even turn to say “goodbye” to me as he walked in! He just sorta rode into the front doors with the wave of familiar neighborhood kids, a wide smile on his face. But, now that we are a few weeks in and the novelty has worn off, he feels sad about going to school.

This morning he cried as I dropped him off. My heart ached as his big blue eyes welled with tears and his little arms reached out to me. As I handed off a weeping Ben to the teacher waiting by the front door, I felt so cold-hearted for a moment: how could I leave that little angel face behind?! I thought back to dropping Evie off at school for the first time six years ago, and I remembered feeling terrible. I wonder if any other first-timer parents saw me today and thought I was the cruelest parent on the planet!

But, with all these kids of mine I now know a thing or two about dropping kids off at school. Shortly after kids walk into their classroom they relax and have fun. Today when I picked Ben up he ran out to me and gave me a big hug and declared “this is the BEST day!” The entire walk home he chattered about his day at school. Maybe I’m not the cruelest parent on the planet afterall…!!!

Here are my tips for handling the tearful goodbyes:

1. Don’t give kids an option: As the year goes by and Ben settles in, I’ll probably give him more than a few days off from school (he’s only 3, afterall!). But, this early in the year he needs to appreciate the routine.

2. Let the teachers handle it: I could easily spend 20 minutes coddling and cuddling him outside the classroom, but that doesn’t help Ben get more comfortable at school. He needs to trust his teachers to comfort him, and he needs to gain self-reliance.

3. Remain calm and confident: I always listen to what the kids are concerned about and ask questions to help them clarify their feelings (“Why don’t you want to go to school?” “Are the kids being nice to you?” “Does circle time/recess/Spanish/etc make you feel nervous?“). Sometimes kids just want to be heard. School is a really big deal to kids, and what happens there is always a big deal.

Plus, it does my kid no favors to see me blubbering away at drop off. If I exude positivity and peacefulness, they will, too (eventually).

4. Remind them of the fun we’ll have together when I pick them up: I like to let the kids know that we’ll make banana bread or have hygge on the sofa once they come home. Or, I ask them what they would like to do, and if their request is reasonable I make it happen (for example, today Ben said he wanted to make an apple pie so we did that when he came home).

5. Say “I love you”: this is always the last thing I say, so no matter what the little fella knows that Mama really does love him.