That Time I Cried In Front of My Daughter’s First Teacher

I remember sitting anxiously in a chair designed for a tiny human, jotting down notes about extra clothes and circle time activities. I looked around the room and admired the sensory table and the inviting crafts hanging on the wall. Here I was, parent orientation at Kennedy’s first preschool. In a week it would be my daughter sitting in these chairs without me. I wouldn’t be there. And I was absolutely terrified.

C must be for Crying, because that’s what I did when I met my daughter’s preschool teacher!

The other parents shuffled out of the classroom and I awkwardly lingered behind in hopes of chatting with her teacher for a few minutes. Here was the woman who was going to be Kennedy’s very first teacher ever. The first person I’d leave Kennedy with who wasn’t related to her. Yes, logically I knew that it would only be for 2 hours 2 times a week. However, any time we had been apart up till that point she was with a highly vetted individual (aka my own husband or my own parents) and I could easily check in on her. Other than that, Kennedy had been with me practically every hour of every day of her life. We had been inseparable. From the day she was born, my high-needs baby made it quite clear that no one was going to stand in for me. It took her a long time to even accept that my husband was also her parent. Life was usually “Kennedy and Mama”. Friends had to accept that what Kathryn did, Kennedy did. I’m sure it drove people nuts and got me a lot of eye rolls, but that was what she needed and I wouldn’t change a thing.

Now I was going to drop my little girl off at preschool with people I hardly knew and leave her there. The thought of it made me lose my breath. I wasn’t ready for this. Before I knew it I was standing in the middle of the most happy colorful room with tears rolling down my face in front of a perfect stranger blubbering about how scared I was. Yup, I was the mom who managed to cry in front of my daughter’s teacher the first time I met her.

We started Kennedy at preschool right when she turned 3. I was excited by the prospect of having a few hours a week to go for a long run or get a few things done alone, but I’m also an anxious person and tend to catastrophize things I’m worried about. Despite my own personal fears, my gut told me that the experience would be great for my little girl and would really help her gain more social confidence. Kennedy is a very smart kid, she’s very verbal and soaks up every little fact you throw her way. She has a beautiful imagination and a thirst for nature and exploring. We love spending our days together playing and learning and going on fun adventures. But despite my occasional meltdowns, I am not a 3 year old. Even with all the classes we did together and play dates we had, she needed a place that was all hers to really explore socially and find that confidence and independence I knew was in her.

Kennedy starting school brought up a lot of fears for me. How was my smart, sensitive, sweet girl going to do without me right by her side?

You see, Kennedy is also a very shy kid. New adults, especially males, make her apprehensive (not a bad trait at all), but she loves kids and making new friends. She just likes to first sit back and observe, take in her environment, and join when she is ready. Despite having a bursting and assertive personality at home, she was often quiet and more passive with peers. She was always so kind and caring with friends, but almost to a fault. If a conflict arose, she needed my encouragement to stand up for herself. I was always there to support her and help her through the hard stuff. She is such a sensitive soul and feels things big. Typical toddler interactions could leave her feeling truly hurt. Her empathetic nature meant that if others did things like push or use a bossy voice, she genuinely took it personally. I was always there to encourage her to be assertive and help her work through those tough toddler feelings. I never aimed to fix things for her, but I was by her side to help navigate the world and give her a huge hug whenever she needed it.

I wanted more than anything for her to feel confident without me standing by her side. I wanted her to be assertive with her friends and make her voice heard. Since we knew these attributes were already in her, we thought her experience at preschool would be a great way to bring them out with her peers as well. Kennedy was excited by the idea of preschool. She picked out a new dinosaur backpack to go along with her new dinosaur dress. But she was apprehensive about that whole me leaving thing. And honestly, I was even more scared.

Kennedy and I were always together, and it was hard for me to realize how sad I was at this huge milestone of her going to preschool. My little girl was growing up.

What would it be like for her without me right there? Would she be ok? What happened if her feelings were hurt or she got scared? What if she desperately needed me and I wasn’t there? Despite knowing how strong and amazing my daughter is, my neurotic irrational brain was terrified that she would just be lost without me. Then, as I sat there crying in front of her teacher, I realized something. Yes, I was scared, and that was ok. It’s a mom’s job to worry. But a lot of my fears were also sadness. Sadness that my baby was now a little girl. Sadness that Kennedy was growing up and no longer viewed the two of us as a single unit. She was her own self- her wonderful, incredible, and amazing self.

One of the hardest concepts to accept was that my daughter actually didn’t need me there 24/7 to protect her. She is such a strong person, and she can fight those fights herself. She knows that I always have her back, but she also knows that I believe in her 100%. As hard as it was to let go a little, I knew that she would be ok, she would adjust, and she would thrive. And after those two hours apart, she’d be right back in my arms to tell me all about it.

My little Elf, all full of smiles while celebrating Valentine’s Day at school! Her teachers and peers all loved and supported Kennedy, elf magic and all!

I won’t say that those first drop offs were all rainbows and butterflies. No, there were tears. Despite a summer singing Daniel Tiger’s “ Grown Ups Come Back” and a special “Mama Magic” locket with a picture of her and I looped around her neck, the goodbye was really hard. With my eyes covered by dark sunglasses to hide my own tears, I put on my bravest face and reassured her. My heart felt like it was being ripped from inside me, but I knew that if she could sense my anxiety then we’d never get through this. That first month was hard. I remember multiple phone calls to my husband declaring that I had forever traumatized our child and ruined our strong bond. At what point do we call it a day and try again next year? Then five minutes later the school would call to tell me that Kennedy was doing great and playing with her friends (yes, they were so wonderful to not only Kennedy but also me!). She was safe, happy, and growing. I could breathe and go get some things accomplished solo.

Before I knew it, it would be time to pick her up. I’d walk in and she’d give me the biggest hug and show me everything she did that day. She missed me, but wow how she was thriving. Then one day, not long after, there were no tears saying goodbye. She would count the days until she next had preschool and I’d count the days until my much-coveted Target trip alone. Her teacher would tell me how wonderful she was doing, how empathetic she was with her peers and how she taught the whole class something new about dinosaurs that day. The entire school staff knew her and that she loved to be an elf. She was part of a community who respected and loved her for her. My heart grew and I witnessed her confidence soar.

What a year! Kennedy gained so much confidence and grew so much! And hey, this mama grew a lot too!

On the last day of preschool, I wrote her teacher a thank you note. I gave the usual thanks for being so selfless and so caring. I also thanked her for letting me cry that day. I thanked her for respecting my fears and providing me reassurance that my daughter was in great hands. I thanked her for not making me feel like a fool because it was so hard to take this first small step to my daughter becoming an independent human. I thanked her for helping me realize how strong my own child was and how this experience would only bond us even more. I thanked her for helping me grow up as a mom just as much as she helped Kennedy grow up as a person.

And those tears- those tears of fear and sadness- they are now tears of happiness. I couldn’t be prouder of my sweet, sensitive, and smart little girl. I can’t wait to see how much she grows in the next school year.


Kathryn is a mom of 2- her wise sensitive Kennedy (7), her sweet little joy, Croix (2), and 3 wild and crazy fur balls! After finishing grad school in NYC, Kathryn decided to embrace the cold and move to Madison. Despite plans to only live here for one year, she fell in love with her husband Joe and all the city has to offer. She loves staying at home full time with her kids during the week and spending a few weekends a month as a social worker in the ER. After a childhood of moving around internationally, she has enjoyed putting down roots in Madison but still loves to travel as much as possible. When not adventuring with her family, you can find Kathryn running around her neighborhood and local trails, writing with a strong cup of coffee, or covered in dog hair from all the furry friends in the house!


Please enter your comment!
Please enter your name here