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A year ago, I committed what is known as a “mom fail” (basically any false move committed during the act of mothering). Preparing my then-2½-year-old son to go out in the morning for a play date, I asked him, “Do you want to go to H.’s house?” Emphatically, he said no. “Well, we have plans; he’s expecting us,” I amended lamely. My son burst into tears, and no matter how I tried to spin it, he was adamant. Maybe he was tired; maybe the dark, cloudy morning visible from our windows was too uninviting. Whatever the case, I was now in the awkward position of having to drag him, kicking and screaming, down four flights of stairs (we lived in a walk-up) while also toting my younger boy, then an infant. So I canceled the play date (thus committing a “friendship fail,” too, all in one morning).

Inwardly I told myself that I would never do that again, but I was thinking in terms of specifics: I will never again ask my children whether they want to go on a play date that I have already arranged. Then I looked at the larger issue, which is my tendency to ask my kids almost everything. “Do you want to put on your shoes now?” “Should we have macaroni and cheese for dinner?” “How about you go brush your teeth?”

These are questions that present a problem if they are answered with no, because they are not really choices. If we’re going outside, we need shoes. If I’m preparing mac and cheese for dinner, that’s what we’ll be having. And we all know what happens when we don’t brush our teeth: cavities, hygiene issues and a future of dentist bills.

I know I’m not alone with my “Ask, Don’t Tell” approach. At the time of the Play date That Wasn’t, we were living in Park Slope, a neighborhood in Brooklyn that is famous (or infamous, depending on whom you ask) for being a yuppies-with-strollers paradise, filled with parents who obsess over school districts, the local food co-op and the merits of buying a two-family home. While living there, I constantly overheard my fellow parents having conversations with their children that could maybe, perhaps, possibly be taken for coddling. “I understand you’re feeling upset,” I heard a mother tell her toddler at a playground in Prospect Park. “Just hit me as hard as you want until you feel better.”

At the time I thought this was outrageous and enjoyed recounting the story to our friends. But then I decided to stop throwing stones and examine the motivations behind my own parenting style.

Why was I resisting giving my sons directives? For one thing, I want them to feel that the world is their oyster, a blossoming of infinite opportunities in which they are never denied. Second, I never wanted to be that mother who yells orders at her children. And finally, I’d read that presenting choices to kids helps give them a sense of control and lessens the tendency toward meltdowns and temper tantrums.

Bibi Boynton, a licensed clinical social worker who specializes in play therapy for children and parent coaching and has a private practice in Park Slope, calls the hesitation to set limits with children a “well-meaning mistake,” but stresses the importance of issuing directives and sticking to them — and emphasizes that parents can do so in a loving way. “By setting limits with your children using clear and nurturing language, you are in actuality providing children with the safety and consistency that they need to have all the freedom you want them to have,” Ms. Boynton explained. “That doesn’t mean you have to bark orders, and it certainly doesn’t mean you can’t sigh and commiserate when your child balks at tooth-brushing.”

Hmm. So instead of asking my older son about the play date with H., and then lamely trying to enforce a command that was disguised as a question, I could have stated it from the get-go: “We are going to H.’s house.” If he’d objected, I could have explained that we had a date and that I truly believed he would have a good time. I could have discussed his feelings and acknowledged them: “If you don’t like playing with H., we don’t have to in the future, but today we’ll keep our date and see how you feel afterward.”

“Children will appreciate you taking a moment to really connect with their feelings and verbalize them,” Ms. Boynton said. “And this sense of being understood will go a long way toward getting the job done.”

And as to the desire for my kids to see the world as limitless, it is the yearning of a loving mother, but there is a profound and obvious problem with it: The world is not limitless. On one side of the spectrum, limitations exist for even the richest, most privileged children. On the other side, there are kids in this country and the world who face limitations every day that range from the relatable to the unthinkable. All children need to learn that their fellow human beings face obstacles — some of them seemingly impossible to overcome. How else will our kids be able to cope when they face obstacles of their own? And how else will they learn to push these boundaries, advocate for others and strive for a better world?

If that sounds like a concept that’s too complex, not to mention heartbreaking, to teach our children, I’m counting on it being a learning curve that unfolds over decades, and a lesson that can begin with a simple command: “It’s time for you to brush your teeth.”