The First Day of School Checklist

Everything you need to make your little one’s first day back to school a happy one.

by Ben Radding
Originally Published: 
A boy going to school for the first time with a backpack

The day has finally arrived. Daycare is over, and it’s time for your little one to spread their wings to go to pre-school, or maybe kindergarten. It’s a scary day for any parent. You don’t know how your little guy or girl is going to like it, obviously, but more importantly, they themselves might be a little emotionally unprepared for school. Not to worry. We’ve sourced the most important things you can do for and give to your favorite first-timer, or even a kid entering kindergarten from pre-school. Don’t forget anything on this list.

A Note

Little gestures — little gifts — can hold great meaning, especially to a child who’s had to leave mom or dad for their first school experience. So give them something to hold on to—even it’s it’s just a note. “I think the often overlooked but very important gift is a hand-written note from mom or dad offering good wishes and support,” says Cara Pollard, parenting coach. “It’s actually the most important gift a parent can give and so nice for the child to have to start the year.”

Clothes from This Year

Nothing makes a kid, no matter what age, feel more self-conscious than if they look time-warped from 1999. “Not that I want to promote kids all looking like each other,” says Meghan Leahy, parenting coach and Washington Post columnist, “but there’s nothing more important to most kids than feeling like they fit in. It doesn’t mean that you have to be a slave to whatever’s hot, or go to the most expensive stores, but even if the parent can do one or two things that that child wants, it makes a big difference.” Check out what other kids are wearing nowadays and act accordingly.

A New Haircut

Nothing says a fresh start like a fresh cut. “A new haircut shows the child that you’re enthusiastic and that he or she are getting ready for the big day,” says Pollard. “And if they like haircuts that would be something that would also add to the enthusiasm.” A fresh cut also makes your kid feel like they’re getting ready for something important.

A Lunch That They Helped You Make

You may be tempted to throw in the usual healthy lunch for your kid — carrots, humus, milk, and all that good stuff — but that’s not really called for on their first day. “Get their buy-in,” says Pollard. “Ask, ‘What do you think you’ll want in your lunch today?’ Asking them to pick out what they want the first couple weeks is always exciting, and even having them help you prepare the lunch might make it seem like you guys are a team in doing it together.” Nothing will help your kid’s confidence more.

The Walk to the Bus

Don’t blow off drop-off or the walk to the bus. No walk is longer for a little kid, and he or she needs dad or mom to help them along the way. “Know that if they’re anxious or worried about getting dropped off at school, the more you can remain calm, the quicker your child will adapt,” says Pollard. Definitely accompany them every step of the way.

Set Up Space for After School

“Most preschoolers completely need downtime” when they get home, says Pollard. So set up a space where they can chill. “Most of them are trying to be on their best behavior, and so they often fall apart for their parents at the end of the day or at pick up.” Create a fresh area where they can play without interruption.

Ask Questions — Very Carefully

You probably will want to know how their day went. Totally normal. But hold your most pressing questions — they probably won’t be up for answering. ” ‘How was your day? Who did you sit with at lunch? What did your teacher say?’ They don’t want to answer any of those questions,” says Pollard. Instead, reframe your questions to get them talking organically. “It’s being open and curious to where the conversation may lead,” she says. “So questions like, ‘What was your favorite thing you learned?’ Or even telling them about your day may spark something about theirs. Don’t barrage them with questions.”

Give a Unique Kiss or Hug

Of course you’re going to kiss your child when they go to school. But you can make it all the more special by turning that kiss into a little secret handshake. “I know that as a mom myself, I had a certain kiss with each kid,” Pollard says. “You see teachers connect to kids that way with doing a certain handshake. If you came up with your own routine of a kiss to make it really fun, they know that that’s a special thing between the two of you.”

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