The Midlife Male is a newsletter and podcast by Greg Scheinman sharing experiences on aging, success, personal growth, and navigating midlife. If someone forwarded you this newsletter, click here to sign up.


I always get sad on planes when I’m traveling by myself.

I’m usually alone, and I’m in between wherever I’m going to or coming from and where I really want to be, which is home.

I find myself looking at pictures of my boys and family. The photo album starts in 2003 when Auden was born and goes all the way up to 2024… Damn, Apple really knows how to make a grown man cry now with these memories video collages they make… and the Kacey Musgrave songs they add in just make the waterworks worse.

My boys are away right now. They’re both out in the world living their best lives right now, and that makes me happy. The sad part is how fast all of this has gone. When I’m not with them, I miss them and just want to be with them.

So it’s a lonely Father’s Day this year. And that’s not to say that I’m a lonely man. I just happen to be alone this Father’s Day and physically separated from my boys.

I’ve been alone from my own father since January 16, 1992

I can’t believe how long ago that seems, and yet it still feels like yesterday that I was in that hospital room, holding his hand as he passed away.

Again, while I’m physically alone, I know he’s been with me spiritually every day since.

How are my boys 20 and 17? When did that happen? They’re literally all grown up. I don’t get it.  I mean, I get it – and I’m certainly getting the bills for it – but I love being able to do things for them.

This is also one of my biggest fears: Not being able to do things for them. My other big fear is that I’ll do too much for them, and I don’t want to be an entitler or enabler of a dad.

I don’t feel old enough for any of this, and yet I do feel every one of my 51 years when I drive by the little league fields in town and see the fathers and sons out there. It seems like so long ago, and I don’t feel like I could do that all over again, which is a reminder that I am in fact middle-aged and that my “young dad” days are behind me.

This is such a strange time of life because, as much as I still feel young, everything I do that a young guy would do physically hurts me. I get so much more tired, sore and agitated… all the time. Except when I get down on the floor with my dogs every morning, because I love that they love me.

Kate and I are in a good place, but I feel like both of us are internally feeling more and more of this “What the fuck is going on?” energy in the pits of our stomachs.

We just order more books on shit that we think can help, or we buy weird little items that other aging parents would order too, like monogrammed travel-size vitamin organizers. And we actually get excited about shit like this too: “Oh, this’ll be so good to take all my supplements with me on vacation.”

We have so much time now. We both do a lot of our own things. We come and go, and live, and love on each other and our boys and dogs, and we sleep a lot more now.

The other day I called her and said “Hey, I’m changing my flight to leave tonight instead of tomorrow, and—”

She cut me off. “You don’t have to explain, it’s all good,” she said. And that felt good. And we are good. Perhaps that’s what 25 years gets you.

Meanwhile, I got a text from a friend the other day whose wife turned 60. And as I was washing my face, it hit me that in a few years I’ll have a 60-year-old wife too! Which means I’ll be sleeping with a 60 year old woman… that’s a complete mindfuck to me.

Life happens, we get older, our kids get older, our wives get older and, if we’re really lucky, we’re actually pretty happy about it even though it freaks us the fuck out.

I mean, for God’s sake, this is my 20th Father’s Day! What?

On quality aging

I was interviewed recently for this article in Esquire about living to 100 and how people will afford it if that really is the future.

I don’t know if I want to live to be 100… Only if my quality of life is good. In living to 100, my mind instantly goes back to sleeping with a woman who will also be 100. Now I’m thinking 60-year-old pussy seems pretty good.

Jokes aside, this is the part about maximizing middle age that’s so convoluted and confusing. You start to experience the same perennial events like Father’s day over and over again. They feel familiar because you’ve experienced them before, but then at the same time they feel very unfamiliar because you’ve changed, the people in your life have changed and your circumstances have changed.

But maybe it’s supposed to be this way. Maybe midlife isn’t supposed to be about keeping things constant, but rather how we navigate change. Whether it be our families, our bodies, our thought patterns or our palates, the only constant is change.

Learning how to navigate change is the challenge of our lifetimes.

Happy Father’s Day, from me to you.

In health,

—Greg


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Did something in this newsletter resonate with you this week? Reply and let me know.

In Health,

—Greg