Wednesday, May 06, 2026

Heartbreak is Part of Both Friendship and Freedom

I came across an interesting tidbit of language information the other day. The English word free comes from the same root as friend. Indeed, it appears that the original root word meant "friend," so, in a linguistic sense at least, free is a product or aspect of friend.

Anyone who has read here for any length of time, knows that I've never focused on academic things in my work with children. If it must be part of a child's life, that can come later, but during these early years, my primary concern beyond safety is creating a loving environment in which children know they are free to engage as their curiosity compels them. That is to say, play. And among the most compelling playthings are the other children who present the prospect of friendship.

Every parent wants their child to have friends, or at least one friend. Our prejudice tends to be in favor of children who are natural friend makers, kids who have the charisma and confidence to throw themselves into the fray. Observational research finds, however, that even these "master friend makers," these most popular of children, are rebuffed at least 30 percent of the time when they seek to enter into play with other children. Which is to say that all of us have extensive experience with social rejection, and is why, I think, we feel it so strongly when we see children struggle with friendship.

I have a few tips I share with children about friendship, which I try to offer in calm moments.

If you hurt people, they probably won't want to be your friend.

If you ask, "Can I play with you?" most kids will tell you, "No." If instead you say, 'I'm going to play with you,' they'll usually say, 'Okay.' But the best way to start playing with another kid is to just start playing with them.

I'm not sure if I've ever helped a child with this advice, even if I've seen the truth of both tips over and over. The kids who can just drop to their knees and get engaged without harming anyone are always the ones with the most playmates. That said, my own daughter Josephine, when she was four, insisted, "But I have to ask them if they want to play with me!" It broke her heart, and mine, when her preferred playmates rebuffed her again and again, but taking my advice was just a bridge too far.

I don't suppose anyone really knows how the word free emerged from an original word for friend, but I wonder if it had something to do with the concept of being free to make commitments to others, which is the essence of friendship. In these first forays into friendship, being a playmate is enough. Two or more children have freely entered into informal, often unspoken, and ever-evolving agreements with one another while engaging in a mutually satisfying activity or project. 

As adults, we see friendship as something deeper, but this is where it begins. And part of this early learning about friendship is also learning that we are free to de-commit. On the playground, the commitment usually ends when the game at hand comes to a natural end or evolves into something else. Sometimes it ends as a kind of emotional eruption when one or more of them cross a boundary. Whatever the case, the old commitments are unmade and the moment of friendship is over. Ideally, feelings are not hurt, but often they are. 

Friendship is something we enter into freely, but the flip-side is that we are also free to leave. Of course, as adults, we have much more experience with the complexities and layers of friendship, but in preschool friendship looks a lot like the ideals of classic anarchy, with everyone free to befriend, de-friend, and make new agreements with everyone else.

One of my best teachers when it came to early-years friendships was a girl named Katrina, a 3-year-old swimming lesson friend of Josephine's who then became a kindergarten classmate. One day I was driving the girls somewhere. Josephine was upset about a fellow classmate who had been "mean" to her. Katrina replied, "She's mean to me too. When she's nice to me, I play with her. When she's mean, I don't." Katrina's words have become a mantra in our family. Her straight-forward, simple statement fully embraces friendship, freedom, and boundaries. It includes the promise of friendship, the reality of challenges, and the expectation of reconciliation. Most of all, I admired the calm, matter-of-factness of how she said it. 

We don't get to choose our family, but we do get to choose our friends, and the only way we learn to do this is by practicing. Through this we come to know that heartbreak is a part of both friendship and freedom, and that we protect ourselves with boundaries. And most of us, if we are lucky, will get to practice friendship every day of our lives.

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Even the most thriving play-based environments can grow stale at times. I've created this collection of my favorite free (or nearly free) resources for educators, parents, and others who work with young children. It's my gift to you! Click here to download your own copy and never run out of ideas again!


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