60 Years Old. With a Roommate.

What nobody tells you about starting over

I stood in the kitchen aisle at Target staring at spatulas for a long time.

Spatulas.

I didn’t know there were that many kinds of spatulas. Silicone, stainless, slotted, offset, fish spatula (which, apparently, is a thing). I’d been married for 24 years. My ex-wife handled the kitchen. I handled the income and expenses. That arrangement worked great - until it didn’t, and suddenly I was a 59-year-old man who didn’t own a can opener.

No one prepares you for this part. The big stuff: the grief, the legal mess, the financial hit… people warn you about that. Books cover it. Your friends mention it in low voices over drinks. But nobody tells you about the Tuesday afternoon where you’re standing in a store realizing you don’t know if you need a sheet pan.

Stocking a kitchen from scratch is humbling in ways I can’t overstate. What, exactly, am I going to need in order to cook? Hard to know when I don’t know how to cook, or what I might be cooking.

I didn’t learn to cook until I was 59. Not “I wasn’t a great cook.” I didn’t cook. I could make scrambled eggs, and that was about the extent of my skills.

Grocery Shopping

Grocery shopping was its own education. A friend told me early on: shop around the outside edges. Produce, meat, dairy. The middle aisles are where the processed garbage lives. Sound advice. But he didn’t mention that I’d be standing in the produce section not knowing the difference between a shallot and a small onion.

I also discovered that a man over 60, alone in a grocery store on a weekday afternoon in a family neighborhood, can attract a very specific kind of look from other shoppers. It’s somewhere between pity and curiosity. Like watching a bear try to use a vending machine.

The Apartment

I rented furnished, which sounds like a solution until you see what “furnished” means in practice. My new place was four walls and the bare minimum to keep it from being legally empty. A small couch. A bed. A table. I never bought a single thing to warm it up. No art, no plants, no throw pillows (I didn’t even know what a throw pillow was for).

It looked like a safehouse. If the cops had raided it, they would’ve assumed I was about to flee the country.

Laundry

Twenty-four years of marriage and I’d never once thought about what temperature to wash anything.

Darks, lights, delicates. I didn’t know clothes had categories. I threw everything in together, hit whatever button looked right, and hoped for the best. It took exactly one load to learn that a red t-shirt and white towels are not compatible. I became the proud owner of several pink towels.

The Closet

Then there’s the wardrobe situation. I looked in my closet and realized everything in it was selected or approved by my ex-wife. And most of it was at least 5 to 10 years old. I was dressing like a man who peaked in 2009 and decided to just ride it out. Cargo shorts. Oversized t-shirts. Sneakers that could generously be described as “comfortable.” White socks.

Once again, YouTube to the rescue. I found a channel called Alpha M. The guy was younger than me, but I not only liked his style tips, I liked how he explained them. Helped me a lot, although I did spend a few months figuring out what my particular style would be. What fit me, and who I was now.

Getting my style together was one of the first external signals that I was actually rebuilding, and not just surviving.

Dating at 60

No one should have to learn dating apps at 60. I’m convinced they were designed by people who hate human connection. Swiping endlessly, (barely) matching, getting ghosted, the photos that look nothing like the actual person. I felt like I’d been dropped into a foreign country without a phrase book. My first few exchanges read like a man who’d been frozen in 1998 and thawed out with a smartphone. Because that’s basically what happened.

Learning to approach and talk to women again was its own ordeal. I’d been off the market for over two decades, and I wasn’t very good at it before I got married. The rules changed. The landscape changed. I changed. I had to relearn everything from scratch: how to carry a conversation with a woman who wasn’t the wife of a friend, how to read signals, how to not come across like a desperate man at a buffet. That last one took way longer than I’d like to admit.

Finding Friends

Finding male friends as a single man in his 60s is harder than people think. Most of my friends were married. Married guys operate on a different schedule and a different set of permissions. Getting a buddy to grab dinner on a Tuesday doesn’t happen.

Them: “Let me check my calendar and see if the wife has any plans.”

Me: “OK.”

Them: “How about two weeks from Thursday?”

I don’t blame them. That was me not long before. But it left me with a social life that was pretty wanting.

I had to find guys who were either single, divorced, or widowed. Men who actually had the freedom, the desire, and the time to build friendships. That took time. And it took being willing to show up to things alone, which is its own brand of uncomfortable.

The Being Alone Part

That’s the one nobody can coach you through. You can read about it. People can tell you it gets easier. And it does. But the first six months of sitting in a quiet apartment on a Saturday night when you used to have a house full of noise… that rewires something in your brain.

I made a huge move from Utah to San Juan, Puerto Rico. A guy I’d connected with in an online men’s group lived there, owned a cigar bar, and proceeded to introduce me around. For about a year it was great. Head over to the bar on very little notice, text one or two guys at 5:00 and say “Up for a cigar and a whiskey at 6?” Everyone shows up. Easy.

But eventually the group dynamic faded. Life got in the way, guys got busy. And the last few months in San Juan had me facing what I’d masked with bourbon, cigars, and company: a deep sense of loneliness and disconnection.

I turned 60 in Puerto Rico. No party, no plans, no one organizing anything. That one hits different. Birthdays in a marriage just happen: someone plans it, people show up, you blow out candles and pretend to be surprised. When you’re single and new to a city, turning 60 means you’re sitting in a sparse apartment on your birthday wondering what you’re going to do with your evening. Fortunately one of my new friends found out I had nothing planned and he and his wife took me out to celebrate. I was more grateful for that than they probably realized.

I ended up in Nashville.

Built and sold two major websites.

Married for 24 years.

Served in the Navy.

And now I was 60 years old with a roommate.

He ended up being one of my best friends. But the single life still felt empty. I dated here and there. Learned salsa dancing. Still empty. After a few months, I finally decided I was OK not being in a relationship. And that was the real shift: not finding someone, but settling into being OK with myself.

At first I ate dinner alone at restaurants and pretended to be fine with it. Eventually, I stopped pretending. I actually was fine with it.

A couple months later, I met the woman who would end up being my wife.

“Forget the former things; do not dwell on the past. See, I am doing a new thing.”
Isaiah 43:18-19

That verse is hanging on a wall in our home. It was the theme of our wedding. I didn’t find it. It found me, somewhere between the pink towels and learning to be OK at a table for one.

The Point

You’ve got to learn to be okay in your own company. And for a lot of men, especially men who defined themselves by their role in a household, that’s brand new territory.

Here’s what I’ve learned from all of it: starting over at 60 is ridiculous. It’s awkward and humbling and there are days where you feel like the whole world got an instruction manual you didn’t receive. You’re a beginner at things teenagers handle without thinking.

But awkward means you’re moving. Humbled means you’re learning. And that guy standing in Target staring at spatulas? He went home, cooked a halfway decent stir-fry, and ate it at a table setting he picked out himself. Now? I cook the best damned steak you’ve ever eaten.

That’s not decline. That’s a man who decided to start.

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Vic built and sold ScreenRant.com and GameRant.com, then rebuilt himself in his sixties.

He writes at TheRedeemedSecondHalf.com for men rebuilding the second half of life.