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Tough Stuff

Why we should teach boys it’s okay to be sad.

By Danny O’Neil October 22, 2025

A person in a hoodie stands alone at night, leaning against a brick wall with red tiles, partially illuminated by a streetlight, capturing the quiet grief and boys' pain in the stillness.
Photo by Warren / Unsplash

This article originally appeared in the September/October 2025 issue of Seattle magazine.

I was 13 years old when my father died.

It happened on a school night, and I remember my mom waking me up along with my younger brother and sister.

“He’s gone,” she said, bringing us out of our bedrooms.

The news was back-breakingly sad. It was not, however, sudden. My father, whom we all called Pop, had been sick for many years. He had Still’s Disease, a rare inflammatory disorder, which began causing soreness and fevers in his early 20s, and ultimately crippled him as he entered his late 30s. It was hard for him to even get out of bed for the final few weeks of his life.

Pop was 38 when he died, and that night, the pastor of our Catholic church came to the house. He was wearing a houndstooth walking hat, and at some point, he placed his hand on my shoulder and said in a low voice, “Tough one, kid.”

People tend to recoil when I tell them the priest’s words, horrified that a man of faith didn’t offer anything more profound. At 13, however, I felt legitimately consoled. I thought he was treating me like a man, and this was how men handled everything from a challenging job to a devastating loss—with a stiff upper lip. Now, in retrospect, would therapy have been more helpful? Hard yes. I probably didn’t need to see my Pop’s body, either, but that also happened because I was born in 1974, and back then, parents didn’t worry nearly so much about the occasional fistfight or the long term impact of actively repressing emotional trauma.

This approach does have certain advantages, though. It keeps you moving forward, and that is a definite benefit in a world that is as difficult and heartbreaking as this one can be. I became a diligent student who graduated from college and then pursued a career as a sports journalist, a profession I clocked as my dream job back in junior high. I tended to think that I had done pretty well when you considered the loss my family had suffered.

It turns out there are some drawbacks to trying to tough everything out. Unexpressed emotions find their way to the surface eventually, and in many cases, repressing those feelings only makes them stronger. I spent a great deal of my teens and 20s assuring everyone around me that I was okay, even on those occasions where I was very much not okay. As a result, I’ve spent a decent chunk of the past 20 years in therapy untangling some fairly tricky psychological knots. Because of that work, I think I understand myself much better.

I also think boys would benefit from knowing that it’s okay to be sad. In fact, it’s not only okay—it is absolutely unavoidable. You will suffer losses in your life. Big, knee-buckling ones that will test your emotions and challenge your beliefs. When they occur, you don’t have to pretend that they don’t hurt. This approach may not easily fit in the typical model of masculinity, which equates keep-your-head-down perseverance with strength, but that’s all the more reason it should be said out loud.

The comedian Bill Burr has observed that when men experience a negative outcome, they are allowed to react in one of two ways: they can be mad, or they can be okay. People laugh when he says this, but he’s not joking. And while I wouldn’t say that anger is encouraged in men, it is certainly tolerated. For a little while, at least. Throwing a fit may release some pressure that results from a negative experience, and then, once that’s out of your system, you need to be accountable and get back to the business of being stoic or strong. The other option is to take it in stride; to motor on.

If we want men to have more emotional bandwidth—to be more empathetic about the difficulties that others experience—we should teach boys that expressing grief and admitting they’re in pain are not signs of weakness, but rather proof that they are human.

There are times when it hurts to be in this world. We don’t need to downplay or hide this fact. The night my Pop died, there was nothing anybody could have said that would have eased the pain of that moment. The priest did his best, and like I said, I felt almost flattered that he was treating me like the strong man I hoped to become.

In retrospect, however, his response is an example of how boys are easily and often pushed to minimize their own emotions. My father’s death was not a challenge to be faced nor an obstacle to overcome. It was a loss whose shadow I can still feel 37 years later. I used to think there was nothing to gain by dwelling on the sadness of his death. I was wrong, though. I’ve gained a great deal of perspective by acknowledging how I’ve felt about some of the more difficult events in my life.

The loss of my father won’t ever stop hurting, but the pain I feel is a testament to the impact he had while he was alive. I am still sad he’s gone, but saying that also allows me to be very grateful for the time he was here and the years we spent together.

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