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A Terrible, Horrible, Not-So-Good, Very Bad Preschool Transition

A Terrible, Horrible, Not-So-Good, Very Bad Preschool Transition

By Amalah

Please help me, oh wise and knowing Amalah. I have read the entire internet and have no idea what to do next.

My son, who turned 3 in June, started preschool about a week ago and the transition has gone… not well. Every morning has been at least an hour of tears and clutching hugs and a series of heartbreaking comments about missing Daddy snuggles or being a little too little to go to school. He cries as I drive him to school, carry him in to his classroom, sign him in, leave the classroom and blow kisses at the good-bye window. His teachers say he listens and participates, but stays teary throughout the day. Even his sleep is interrupted by little crying jags.

Here’s what we’ve tried to do so far to help him adjust:

  • Leading up to the first day, we read books and watched a few TV shows about going to school (LLama LLama Misses Mama, Daniel Tiger, etc.)
  • We visited his classroom twice before school started so he could meet his teachers and see all the COOL STUFF that happens at preschool.
  • We let him help pick out fabric for a nap blanket that has ties around the edges just like his lovey at home.
  • I’ve tried to be cool and confident at drop off and reassure him that he’s in a safe place and mommy or daddy will be back at the end of the day.
  • We’ve talked a lot about his feelings. We’ve told him that’ it’s normal to be a little nervous while he adjusts to something new, and tried to give him quick coping techniques for the moments he feels sad (we store kisses in his pockets, tell him he can tell his teacher or a friend how he’s feeling, remind him play with the awesome Legos in his classroom, etc.)

At this point I don’t know if we’re reinforcing his sadness by giving it too much attention, or if we’re cold-hearted monsters who are doing irreparable damage to our kid’s psyche by continuing to make him go. I need perspective. Is this normal? Should we be changing our approach? How do we snap out of a routine of sadness?

Thank you so much!

It’s hard to make Big Sweeping Judgments after one week of school, because he could just need more time.

Or he might not just be ready for preschool at 3. Or he might not be in the right preschool for him.

Because really, you’re doing everything right and just about everything I’d probably suggest to someone in your position. It’s completely normal for early preschool drop-offs to be full of tears and drama, but ideally the tears should vanish the instant the separation is “final” and the child then moves on with their day just fine. A child who stays teary all day (and crying at night from the dread of school) is having more profound separation issues than what I’d consider “normal.”

(This is not to say a 3 year old who cries all day at school or daycare is ABNORMAL by any means, just that it’s not something I’d just wave off and say “oh, just give him more time, he’ll be fine.” It’s more concerning to me, is all.)

Some things to try to help:

1) Send in a photo of you and your husband that he can look at when he misses you. Maybe something on a small keychain he can keep in his pocket and fidget with when he’s feeling anxious.

2) Set up playdates with his classmates. It might help if he can arrive in the morning looking forward to seeing a specific friend or two — more of a “hello!” than a long protracted “goodbye.”

3) Beyond that, make sure you really, really like and trust his teachers. Get updates from them on the crying and ask specific questions about what they do to help him. Can he get hugs? One-on-one redirection? Giving him a visual schedule so he knows what to expect next (and exactly how long he’ll be there). Or are they just sort of waiting around for him to snap out of it one of these days?

Trust your instincts on how much longer to give him — the crying at drop-off is one thing, but ideally the sadness needs to stop spilling over throughout his whole day. And DEFINITELY no crying jags at night and a solid hour of tears in the morning.

Speaking of the drop-off

MAN, that drop-off procedure sounds like a pain in the ass. Parking your car, carrying him down hallways to the classroom, staying there to sign him in, waving through a goodbye window, OY. So many steps for him to go through while dreading the inevitable. So many opportunities for him to beg you to change your mind.

I’m biased here — we had a similar routine at our very first preschool and saw SO MUCH CRYING, while our current (Montessori) preschool does drop-off very differently. It’s like ripping off a Band-Aid. Parents pull up to the curb in their cars, a teacher or aide gets kids out of their carseats and walks them inside, usually in little packs of two or three. Bam. No long goodbyes or extra hugs or “one more kiss” or waterworks. I’m usually driving away before my child is even all the way inside because there’s someone waiting behind me. It’s abrupt, but IT WORKS, and they handle it like this very much on purpose to prevent the separation problems. (Any time I’ve arrived late and have to walk my kids inside myself, they get very clingy and unsure of themselves, whereas at the curb drop-off there’s zero hesitation.) Maybe you could talk to the school about the possibility of someone picking him up at the front door and taking him to the classroom? Or just find a differently structured program/school with a more efficient drop-off routine.

I have a 3 year old with a June birthday so I know your timeline math: You want two years of preschool before kindergarten at 5. And I would totally agree (you know I love me some extensive preschool experience), but the reality is that not every kid is ready for preschool at 3. And not every kid is ready for kindergarten at 5 — especially if they’re a “young 5” in September, if that makes sense. Your son might benefit from preschool, but he might also benefit from another year of maturity, when he’ll be more ready to have a POSITIVE preschool experience. But it’s probably too early to say for sure, after just one week. Again, trust your instincts here. Set a mental timeframe for improvement (plus try the photo object + playdates) and reassess more seriously then.

More on Back-to-School from Alpha Mom:

  1. How to Get Into the Back-to-School Swing 
  2. DIY Stree Ball for Fidgety Students 
  3. Make Back-to-School Week the Easiest Ever 


If there is a question you would like answered on the Advice Smackdown, please submit it to amyadvice[at]gmail[dot]com.

About the Author

Amy Corbett Storch


Amalah is a pseudonym of Amy Corbett Storch. She is the author of the Advice Smackdown and Bounce Back. You can follow Amy’s daily mothering adventures at Ama...

Amalah is a pseudonym of Amy Corbett Storch. She is the author of the Advice Smackdown and Bounce Back. You can follow Amy’s daily mothering adventures at Amalah. Also, it’s pronounced AIM-ah-lah.

If there is a question you would like answered on the Advice Smackdown, please submit it to [email protected].

Amy also documented her second pregnancy (with Ezra) in our wildly popular Weekly Pregnancy Calendar, Zero to Forty.

Amy is mother to rising first-grader Noah, preschooler Ezra, and toddler Ike.

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