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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.)

So 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.”

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, though: 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.

Find more Back-to-School Ideas here!

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

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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  • Carolyn

    August 29, 2014 at 2:44 pm

    I have a different situation that kind of sort of applies, so I guess take it for what it’s worth and toss it out the window if you don’t find it helpful 😉 My 3 year old had been in private speech therapy for over a year and at 3 began having it in small groups at his future elementary school. He was SO excited about going to school and we talked about it and had a social story about it and all kinds of reinforcements in place, and it was just a DISASTER. I had to pull him off my legs and deposit him into the classroom and then bolt out while he was screaming bloody murder. For the first few weeks I’d return 30 minutes later and he’d barely have recovered (even though he would have spent the entire class hiding under a table and trying to take off his clothes. Kids are weird sometimes). I kept trying to better prepare him for the experience, and it just kept backfiring. He started getting anxious and worked up about school the night before we’d even be going and he’d start freaking out and melting down every morning when I’d wake him up. It was AWFUL 🙁 It got less awful really slowly and by the end of the school year a month or two later, he was totally happy to see his teacher and would run into the classroom without any hesitation. (He starts again in a few week and I’m TERRIFIED we’ll be starting at square 1 again!) Anyhow, something that the whole experience really taught me was that while I’d always known my son was a slightly anxious little boy, I hadn’t realize how my attempts to help him were doing more harm then good. I was always letting him know that in a couple day he’d to go school and see his friends, or that tomorrow we’d go see Mr. Matt, and every reminder started him ruminating and then getting too wound up and weepy and panicked to sleep that night. So some kids REALLY benefit from warnings and reminders about upcoming transitions, but I learned the hard way that mine REALLY doesn’t. He’s much better if I casually mention it maybe once the day before and then again when I wake him up in the morning, but if I make a big deal about it or make him think too much about it, he just can’t control the thought process. So I am thankful to the experience for teaching me more about my little boy … but my heart breaks for you because it sure is hard :\ (But light at the end of the tunnel – it might work out to be totally fine!) 😉 Good luck!

  • Hermia

    August 29, 2014 at 3:26 pm

    It seems like he’s in an all-day program. Is there an option for half days or shorter days? Maybe he’s just not quite ready for a long day.
    That said, we’ll see what my almost-3-yr-old does next week when it’s her turn. She’s super excited about it in theory, so I’m hoping that carries her through, as so far she’s not been too keen on other kids…

  • Jess

    August 29, 2014 at 3:27 pm

    My son started daycare (as opposed to his previous nanny set-up) right around his second birthday, and the transition was rough for him too. It wasn’t quite like this as far as the crying and dreading it beforehand, but also, he was a year younger than yours is now and so we weren’t able to have the same kind of preparedness conversations that you had with your kiddo. But we did have the same situation at school, which was, in addition to a tragic wailing goodbye, ongoing tears and general sadness and weepiness throughout the day, especially during down time or transition time or any time when he had a moment to stop and think.

    It lasted for a few weeks (the timeframe was exacerbated by the fact that he was only there two days a week so he never knew what to expect on different days and it took longer for him to adjust because he wasn’t there as regularly), and after a few weeks when it didn’t seem to be getting any better, the daycare jumped in with a new suggestion. They had two classes for his age group. One of them had two teachers and 14 kids, and the other had one teacher and 7 kids. He had been placed in the larger class, but they suggested that maybe he was feeling overwhelmed by the size and chaos of the class, and so they did some switching around and tried him in the smaller class instead. That made a HUGE difference. Within a day, he was much happier at school, goodbyes were easier, and he was cheerful all day after we left. Within a couple weeks he was asking to go to school every day and complaining on the days when he didn’t get to go. It was SUCH a huge relief.

    Not sure if, or how, our solution might help in your particular scenario, but I wanted to share it because if there are options for possibly changing things up for a little bit, getting him more small group time, etc., those might help a lot, and also because a thing that really stuck out for me was that the daycare took the initiative to observe the problem, report to us about it, raise concern when it wasn’t improving, and proactively suggest a solution. I would expect the same kind of response from your son’s preschool. In our case, not going to daycare would not have been an option due to our childcare needs, but at age three, it is my very strong hunch that there IS a preschool setup out there that your son will be happy at. And maybe it’s even the one that he’s in now. And I think a big differentiating factor there will be how proactively the school tries to work with you to ease him in. And if the answer is not very, don’t get discouraged thinking he’s not ready for preschool–I bet there’s another one out there that will meet his needs much better.

    Good luck! I hope things improve soon.

  • Kimm

    August 29, 2014 at 5:41 pm

    Is your little guy ever away from you in a different setting? Maybe try going to a Mothers of Preschoolers (Mops) group, to church & leave him in the nursery, anywhere else where you leave him for a shorter time and then come back. It might help him realize that its ok, you will come back no matter where you go.

  • leslie

    August 29, 2014 at 6:38 pm

    Hopefully in a couple of weeks it will get better. Ours wasn’t quite as dramatic when we moved and switched preschools, but it did take some time. We have great providers who worked with us through the transition (and she had a ton: just turned two, in her own room, new house, new preschool, and she somehow weened, too). One thing they said we could do is they gave us a piece of poster board and said to put a bunch of pictures of family on it. We did that. Family shots, mom and kid, dad and kid, fave stuffed animals, people making silly faces. She seemed to like looking at it and telling people what was in the pics. Our daycare is a taken ’em inside and sign them in type, too, but I find that keeping it short and sweet did help. Sign in, hug, kiss, bye-bye, hand off to a provider, and out the door (no peeking at the window). But really, the daycare people should be able to deal with it by redirecting with a ton of fun. 
    Anyway, Good luck. It’s no fun to see your little one so sad as you leave. But it likely will get better, as long as the daycare is supportive.

  • Jill

    August 29, 2014 at 8:19 pm

    My son was very much the same.  Started preschool at 3 and cried for weeks.  Dreaded going to school, would fight me on getting him out the door in the morning and didn’t want to stay there.  It ended up that he didn’t talk at school.  For the entire year.  After the first few weeks he didn’t cry when we dropped him off but he still didn’t want to stay there.  Eventually he was excited to go (most days) but did not talk. At all.  For a year.  To anyone.
    We switched schools for preK and the drop off was like Amy said, right out of the car at the door instead of walking him to class.  He LOVED that school and eventually even dared to whisper to the teachers and one of the other little boys he liked.  He starts K this year and is so SO excited, and even talked the ear off of his teacher at the meet and greet.  
    Anyway, all that to say sometimes it can take a LONG time for kids to warm up to something new, especially if they are stubborn.  And for us preschool was really the first time we ever left him anywhere without us (other than the occasional at home babysitter), which I think exacerbated things.  

  • Amber

    August 29, 2014 at 8:54 pm

    As a preschool teacher, I can tell you that it will get better! Some kids just take longer than others to adjust, especially of this is their first experience in a school environment. A lot of the time a child’s anxieties come from mom or dad. I’ve seen many kids who are totally fine, but then mom gets worked up and starts saying things like “don’t worry!” “Don’t be scared!” “I’ll always come back, and never leave you forever” and etc. Often, these thoughts never even occur to the child until a parent says them, and then the child can’t move on and the anxiousness stays put. Even just anxiousness from a parent can manifest itself in a child’s behavior. It doesn’t sound like mom is doing this though. 

    It will get better! He just needs time. And if he isn’t ready now, give it another shot next year when he might be 🙂 

  • Nuria Campos

    August 30, 2014 at 12:03 am


    I feel like I’m re-living my our experience when my daughter first went to pre-school. She would start crying as soon as she got in the car “saying please mama no”. When we drove into the parking lot she would start holding tight to the car seat. It broke my heart and it was a real struggle every day. When i picked her up her teacher told me she had cried all day, and as soon as we got home she would just lay on the floor and barely wanted to play. She would wake up in the middle of the night crying and began to such her thumb. I talked to her pediatrician about it and she said we should keep taking her for 3 weeks at least. After the 5th week of crying all day long we decided it was too much. We really liked the place (facilities and her teachers), but she didn’t. We started to look for other places and ended up trying a different day care. She cried the first week, but after that she would wave bye bye and blow kisses!!! We were amazed!! So I completely support the idea that it might not be the right place for him.

    Good luck!

  • Jessy

    August 30, 2014 at 10:00 am

    It really sounds like you are doing all the right things to help prepare him. It might be that he’s just not ready, but it wouldn’t hurt to give him a little more time to adjust. 1 week isn’t much time at all. I taught kindergarten for a few years and the drop off at the beginning of the year was rough on some. Definitely keep your drop off brief and cheerful. The more drawn out it gets the more time there is for him to get more upset. I think sending in a picture of you and him could help. I also had a student who I would let call home at lunch and share with mom what he had done during the morning. . I have had parents prepare a special note or treat in their child’s lunch to give them something to look forward too. Talk with his teachers and see what they are trying and what they are observing. Maybe there is something else contributing to his all day sadness. It could be he is having trouble fitting into the group and needs a little help connecting with the other kids. I hope he settles in and begins to enjoy preschool!

  • SnohoMomma

    August 30, 2014 at 2:11 pm

    12 Days. That’s how long it took my sweet, confident, outgoing 3yr old son to adjust to his new full-day preschool last fall. And it was the loooongest 12 days of my life. 12 days of tears and begging and pleading from him, and then me shedding my own tears, wondering why he didn’t like it, what was I doing wrong, can I find another school this late in the game, how can I possibly quit my job and stay home with him every single day because this is JUST TOO HARD….and then Day 13 came. And drop off was easy. And he SMILED! And kissed me and waved goodbye with no issues. And he pretty much loved every day after. Definitely give it a little longer. But I also agree that mommy hearts can only take so much, so if you feel deep in your gut that this is not a right fit, move on. Good Luck!

  • Elizabeth

    August 30, 2014 at 3:13 pm

    My son did exactly the same thing when he started preschool at 3. Right down to the waking up crying and eventually not eating. After a month of things getting gradually worse I made an appointment to spend the morning there with him. I ended up pulling him the same day— it wasn’t that anything criminal was going on but it wasn’t pretty either ( lots of yelling, shaming and seemingly arbitrary time outs– which weren’t even directed at my son but still it was unpleasant to be there). But in my case there were other kids having similar issues with this (new ) teacher which was a red flag to me. On the up side, we sent him to a lovely new preschool the next year and there wasn’t a single tear!

  • Angela

    August 30, 2014 at 4:00 pm

    Oh boy, I soooo could have written this post. I just started grad school and had to put my 3 year old in full-time day care. I honestly wasn’t anticipating many problems as he’s done fine with sitters, but he reacted in the exact same way as your son did. Every morning he would cry and cling to me the whole time we’re getting ready. Every evening he’d beg “Pweese no more school” as we’re tucking him in, and his teachers reported that he’d cry periodically throughout the day.

    I don’t know what your situation is, but for me staying home with him was no longer an option. I needed full-time care for him. I felt horribly guilty and wondered if I should start looking into other options (despite the fact that he’d been on the wait list for this center for over a year). Fortunately I have a friend who has done daycare for many years and she advised me that unless I have glaring concerns (unexplained bruises, etc) to stick things out for at least a month to give him time to adjust. Last week was the third week and I’m FINALLY starting to see him settle in. I about died the other day when he happily sat down at the craft table and says, “Mommy, please go”. He still gets a little whimpery while we’re getting ready and has mixed feelings about whether he wants to go, but it’s getting better and I feel like this school will actually be a great fit for him.

    So I guess you should start thinking about other options (is it possible to do half days, find a smaller, home preschool, or take him out altogether for a bit?), but I’d recommend sticking it out for a few more weeks to give him time to adjust. What you’re seeing is pretty normal for some kids this age. It could just be a bad fit, but I think that more than likely he’ll adjust within the next couple weeks.

  • Caroline

    August 31, 2014 at 11:44 am

    I would say Amy is giving good advice here, and definitely really examine what you are doing at the time of drop-off that might be making it worse. Too many ”special one last kisses” and all that sort of stuff can actually have the opposite effect. So can rehashing all the drama at home and at night and so on. It’s lots and lots of attention basically. Were it me, I’d get a lot more abrupt *in a kind and pleasant way obviously*, and just drop him off, ignore the tears, big kiss goodbye and see you later! If that doesn’t work in another complete week, then reassess and maybe wait another 1-2 terms. How is he when you leave him other places like with granny or at a friend or with a babysitter? It might be the case that this is totally alien to him – I know several kids who had literally never, ever been left anywhere at all, under any circumstances, till SUDDENLY ONE DAY THEY GOT DUMPED AT SCHOOL. And then… total hysterics, and the mothers were shocked… I know! Seems crazy, but it’s very common. Best of luck, your little guy will ultimately be okay.

  • A.L

    August 31, 2014 at 2:33 pm

    I’m with Amy on the drop off routine bit. It sounds like a lot of steps and a lot of hassle.

    Our preschool doesn’t pick kids up at the curb either, but parents are not allowed in the classroom in the mornings. I take my kid as far as the hallway and while I sign her in with an aid, the teacher brings my daughter inside the classroom. There’s no window or anything so that’s just it. It was a little weird to me at first but I think it does help with the transition.

    If your preschool won’t go so far as to do a curb drop off, maybe you could meet in the middle and work out a system with the teacher so you don’t go in the room with your son?

  • Chel

    August 31, 2014 at 5:41 pm

    I was this child growing up. Crying though out the day, not sleeping. Mine lasted through early grade school.  The only thing that made separation better was to have a friend go with me or meet me at the door when I came in.  Please try the play dates that Amy suggests. Even at my age I can remember the fear I felt being left alone and all I really needed was a good friend in the class to make everything better. 

  • s

    September 2, 2014 at 3:10 am

    All the suggestions are good. I’ve worked in preschools and sometimes it took a month of all day crying. However, staff should be looking for activities that he likes to ease the transition. It might be an issue of a good fit. It also might be the peers. We had a peer issue last year. Is there a way you can observe without him seeing you? The classroom structure may not suit him. Also one person mentioned not feeling alone. It is hard to join a classroom if kids are already friends. Time and talking with staff will tease out the issue. We had kids come on buses so the transition was without parents. off the bus, greet the teacher, have breakfast. Picture cards may help him transition from activity to activity. Also minimize the talking about the issue.just a I know you don’t like this, I will be back, drop off and leave. he has to learn some coping mechanisms like comfort from the staff, holding onto a toy, looking at books,
    Maybe drop off when less busy.  You will find the answer, kids were fine weeks later with no residual impact. Also ignore bystander looks, it just makes it worse. Don’t feed too much into the crying. Hang in there. He will be the one sad to leave at graduation!

  • OP

    September 3, 2014 at 2:41 pm

    Thank you all so much for the suggestions. I think I was ignoring my gut because I was worried about being too overprotective. Ultimately we’ve decided that it’s not the right school environment for him at this point.

    This morning my husband tried to follow up with his teacher about what they were doing in the classroom to help him transition, what we could be doing differently, etc. His teacher’s response was basically that he’s three and they expect him to suck it up and control himself. They won’t be addressing it any further. (After less than two weeks.)

    So… yeah.  Not the right place for us. Hopefully we’ll find an option that works for him. We’re looking at a half-day Montessori program and keeping our fingers crossed. We will be keeping all of this advice in our back pocket to help make the next transition a better one (keeping drop offs short and sweet, not talking about school to the point where we’re exacerbating the problem, finding buddies and scheduling playdates).

    Again, I really appreciate everyone’s responses. This has been a rough couple of weeks and this advice really helped me put things in perspective.

  • JenVegas

    September 3, 2014 at 4:30 pm

    My son has been in daycare since 4 months old. It was dicey there at the very beginning, then it all smoothed out because he really enjoyed it. But right around 2 and a half he started having serious separation anxiety issues at drop off. It was impossible for me to even BE there at drop off or to even show up for school functions without him completely freaking out. So while Amy right be right about him not being ready at his age because it might just be A Thing at this age.
    Now, at 3 and a half, in a new day care, about to start pre-k everything is super awesome again and there’s no drama.
    You are not alone. This too shall pass. Good luck!

  • Jen

    September 3, 2014 at 5:41 pm

    It sounds like you’ve already made a decision to move to a new preschool (understandably so!) But I wanted to add that 3.25 years was my daughter’s WORST period of separation anxiety. She started at our public Montessori elementary at 2.75 (crazy late school year cutoff here) had been at school for 5 months already when she started having daily meltdowns when we’d drop her off in the morning. Like to the point that the teacher called us to come back because she was still crying 25 minutes later and refusing to let teachers or other kids comfort her. It took about a month to resolve completely, but we did find that dropping her at the door of the classroom was the best strategy. I really feel like it was some sort of developmental leap where she figured out that I and her dad do things without her, and that made her very unhappy. So I just wanted ot say, you are not alone! Best of luck moving forward!

  • BMom

    September 5, 2014 at 1:10 pm

    Wow. Yep, with a response like that, its time to move on. My daughter started daycare at a younger age, but she had a really tough time adjusting. Our daycare (which we love and my younger one started attending at 7 mo) worked with us on lots of options. The one that finally worked for my girl was to go to the class and put all her stuff away, and then a teacher would walk with us to a different location- they had a train table by the office – and I would say good bye there and then the teacher would take her back to class. I don’t know if it was having less people around, or what, but it really worked for her. But most importantly – we had a team of teachers willing to come up with creative ideas and work with us! Good luck in the new place 🙂

  • Mary

    September 8, 2014 at 6:00 am

    My daughter is still young, but I imagine if she behaved this way I wouldn’t have made it past a week. Am I too much of a softie? I know for some, this may not be an option, but I would try to find a half day or morning program and try again next year…

  • maree

    September 8, 2014 at 7:57 am

    Great that you are looking elsewhere. I had my son in kinder at 4 and he really struggled with similar problems, I pulled him out and took him to straight to school the next year (the system is different here). He had no trouble and quickly caught up at nine he is doing well academically and socially – he just needed a little more time, trust your gut!

  • Andrea

    September 8, 2014 at 9:24 pm

    My son responded well to “The Kissing Hand” book accompanied by a special bracelet he got to pick out and he wore to school so he could think of us any time of day…worked like a charm

  • Jillian K D

    September 18, 2014 at 12:23 pm

    I’ve seen this before.  I had a student who would cry over the weekend about coming to school.  It broke my heart too (first year lead teacher) as I did everything in my power to try and help her adjust with extra attention/hugs.  Her cousin was in the classroom and that helped a bit, but she still cried throughout the day.  What seemed to work best was letting her leave around nap time.  After a few weeks it became easier and then Mom slowly lengthened the amount of time she spent in school.  She is perfectly fine now.  This particular chain school also had the same situation of parents coming into the classroom to drop of her their children.  It caused more problems than anything with kids having a hard time saying goodbye and some parents lingering causing a distraction during morning circle.  Having previously worked in a montessori school with a drop off like Amalah’s; I have to say that its much better that way.