School Days: Starting my Only Child in Preschool

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It gripped me the day that I got that phone call from the director at the preschool. A spot for Andrew would be available at the school we had selected for him when he was a wee baby at the beginning of their summer session in June.

I knew the day would come where it would be necessary to transition him from the cozy, one on one attention he gets with my parents to a busy, scheduled one with teachers, activities and other kids. But it seems like that day came way too fast. I have been very lucky that for the last nineteen months, my parents have provided child care for Andrew while Scott & I work. During this time, Andrew has grown a very close relationship with his grandparents, and I’m so grateful that they have that bond.

As hard as I tried to push it out of my mind, I also knew that in order for Andrew to flourish and learn, at some point, he was going to have to go to preschool. I had fear about leaving him with strangers, fear about him not eating properly, even a fear about him catching crazy illnesses. I knew that these fears were irrational but I still had them. I had so many questions lingering in my mind about this new transition to school. “Is he ready for a school environment?” “Will he be safe?” “Will he make friends?” “What if he feels left out?” and of course, “What if he feels scared and abandoned?”

It was through a conversation with my best friend that I started to relax about his next big milestone. She is a kindergarten teacher and through her observations, she even said he would be fine and do really well and that there was no doubt that he was ready. I knew in my heart he was, too, as often, when he sees other children, he rushes up to them, says “Hi!” and yearns to play. More than anything, I think we (as in my husband and I) were the ones who weren’t ready to see our baby boy grow up and actually head off to “school.”

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So, on that hot June morning, we tied up his sneakers, and packed his little seersucker backpack, ready for his new adventure. As a family, we headed to his new normal – at the cute little school right down the road  with the ceramic frog  in the doorway. I was so proud when we dropped him off; he jumped right into playing with the other kids and didn’t even notice when we were leaving. He did well that day, only briefly crying a few times here & there. He got home that afternoon and was excited to see us and slept like a log that night. Upon reading the schedule and calendar for the months ahead, I was jealous of all of the fun he was going to have!

Hallelujah, school was a success!

Or so I thought.

The next few days were HARD. I don’t think I’ve ever had to hold back big fat ugly tears as much as I did for those few days. I dropped him off nearly every day that week, and as we arrived to the school, I had a Stage 5 Clinger on my hands. He would scream and cry when I dropped him off, and it took all I had to not let him see me cry. Oh, and my biggest fear (the sickness thing!), well, let’s just say he didn’t make it 5 days before I had to keep him home with a tummy bug that he then proceeded to pass on to us!

The next week was a little bit better. He would cry at drop off, but when I would call (an hour later), the director told me the cries stopped almost immediately and that while he was temperamental, he was still eating, napping and starting to play a little bit at school. Each day, he was warming up to school a little bit more. I felt better that I could call and check on him, and he was sleeping well at night and already started to pick up more words, expressions, and he even would pick up after himself when he was at home!

Photo courtesy Ms. J at Andrew’s School!

Now we are on week four of school, and while we have some days where he is clingy and whiny, I have been assured that the tears end before I can pull out of the school. (I know it’s true because I snuck back in the other day, and he was playing happily less than 5 minutes later!) When we pick him up, he’s happy to see us, but often playing with his new friends and is sure to wave bye-bye to his teachers and blow kisses on our way out the door. He sleeps well through the night, is learning the fundamentals of playing well with others, gaining knowledge and is just blossoming beyond my greatest expectations. Plus, all of the cute crafts he’s been making are SO CUTE!!!

I know now, that making the decision to put him in preschool was the right one, and while I know it will bring around some bumps in the road, like getting shoes thrown at me because he’s not ready to go (yes, that really happened); I know that he will grow by leaps and bounds with each fun filled day! And that fear, well let’s just say, it is slowly fading each day with every positive afternoon pick up.

Did you struggle with sending your toddler to preschool? How did you cope? Do you have any words of advice for adapting to this new routine? 




  1. Like you, my Dad retired to keep Jane at home with him. It was such a welcoming and comforting environment for her. But, we decided to enroll her at St. George’s for two days a week so she could be in a more formal learning environment. I was excited but very anxious about the transition. Jane is a peanut and was about four months younger than most of her classmates. I worried she would get trampled or left out. Turns out – sending her to school was wonderful for her. She adapted very quickly and loved it.

    However, she has cried everyday at camp drop off. Same school. Same teacher. Same friends. WHY?!?! I can’t figure it out. It crushes me. Hopefully, she’ll get back to her adaptable little self and run into her classroom again soon!!

    • Awww poor Jane! Andrew does the same. He cries at drop off, but he stops as soon as we leave and are on the road to work.

      I was so anxious and I’m glad each day gets better and better and he’s starting to really enjoy school! 🙂

      I also feel better knowing I’m not the only one who was anxious about this!

  2. I was so nervous when I got that phone call that Jude was accepted into preschool too! I cried on his first day just as he did. Now he loves it and will be going 5 days/week beginning in September!

  3. Like I have shared, we have ups and downs, highs and lows. Overall, school is a huge blessing for all of us, but that doesn’t make it easy. I can assure you that all of the kids settle down after drop off b/c there have been days where I drop T off much later for whatever reason and everyone is happy, even the kiddos who usually are clingy first thing. He looks so cute as Cat in the Hat!

  4. As you know, Addie starts school in the fall when her cast comes off. I’m nervous but excited at the same time. All of those same questions go through my mind every day! But I really do feel like the benefits she’ll experience will be so good for her (and us!) both developmentally & socially! I’m so glad to hear that Andrew has adapted well! Thanks for sharing your experience!

    • it definitely took a little while, but now he is doing great at school, and I’m so please! I know Addie will, too! 🙂

  5. Andie~ don’t know if you remember but we know each other sort of 😉 went to school together. My son goes to the same preschool- the ceramic frog gave it away- and you will no doubt LOVE it! My Benjamin loves it, he is still asking all summer if he has school. He was in room 3 this school year. We loved every second of it. Hope to see you around in the Fall. 🙂

    • Hey Lauren! Of course I remember you! I know someone else who sends her son there (and he was in room 3, too- and I think you may know her) and she said the same, which helped me so much when we started to send him there. I chuckled when you said the frog gave it away! 🙂

      I am sure I will see you in the fall!

  6. My daughter turned 2 in May and I’ve got that fear of sending her to preschool. I know she’s ready as I’m busy with her baby brother a lot and wish I could spend more time reading and learning with her. I’m going to slowly transition her away from home with a half-day program 2-3 times a week. Otherwise I’m gonna miss my little helper! Will you hold me when I need to double up on Xanax? 😉

    • SURE! I would be happy to! Feel free to email me- I can help you through it. Now that we are almost 6 weeks into him being at school, I can honestly say that it was a great thing we have done. He is learning so much and he has new friends and he’s loving every minute!

  7. School is such a hard decision. It must be a relief to have made a decision and know it’s the right one. We still have NO idea what we are going to do regarding school!
    Yay for Andrew and mommy!


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