Hey! I'd love to hear your thoughts, send me a voice note.

When exactly does it happen? When do you go from being one of the younger people in the room to looking around and wondering why all the doctors, police officers, teachers—and practically everyone else—suddenly look like kids?

In Episode 10 of That Old(er) Guy Show, Jeff takes a humorous look at those little moments that make you realize you've somehow become that Old(er) Guy.

From making noises when you get out of a chair and discussing grocery prices with complete strangers, to suddenly becoming fascinated with the weather, struggling with passwords, questioning today's music, and catching an unexpected glimpse of yourself on a self-checkout camera—getting older has a way of sneaking up on you.

But there's another side to becoming the Old(er) Guy. You've accumulated stories, experiences and memories from a world that has changed enormously during your lifetime. You remember how things worked before smartphones, GPS, streaming, social media and an app for practically everything.

Getting older doesn't mean everything was better back then—or that everything is better now. It simply gives you enough history to appreciate the difference...and occasionally ask:

When did THAT happen?

Join Jeff for a casual, humorous look at aging, changing times and discovering that becoming the Old(er) Guy might not be such a bad thing after all.

That Old(er) Guy Show Real Talk. Real Stories. The Way I See It.

Getting older is mandatory. Acting your age is entirely optional.

Hey! I'd love to hear your thoughts, send me a voice note.

Remember when getting lost was just part of going somewhere?

Before GPS, Google Maps, and that reassuring little voice saying “recalculating,” finding your way meant road maps, handwritten directions, highway signs—and occasionally stopping at a gas station to ask somebody who actually knew the area.

In this episode of That Old(er) Guy Show, Jeff Blair looks back at the days of folding maps that never folded back correctly, directions based on landmarks that hadn't existed for 20 years, family vacations where Dad drove and Mom navigated, and the arrival of MapQuest and eventually GPS.

Technology has made traveling easier, safer, and far more convenient. But has following turn-by-turn directions also changed the way we experience the trip?

There was a time when taking a wrong turn might lead to a little restaurant, an interesting town, a scenic road—or simply a family story that would be told for years.

Maybe getting lost wasn't always such a bad thing.

So grab your imaginary road map, ignore the person in the passenger seat saying, “I told you that was the turn,” and join us for “When Getting Lost Was Normal.”

Because sometimes the wrong road takes you someplace worth remembering.

That Old(er) Guy Show — Real Talk. Real Stories. The Way I See It.

Getting older is mandatory. Acting your age is entirely optional.

Hey! I'd love to hear your thoughts, send me a voice note.

Remember when shopping meant actually going somewhere?

In this episode of That Old(er) Guy Show, Jeff Blair looks back at a time when shopping wasn't just a transaction—it was an event.

There were department stores, shopping malls, Christmas catalogs, and local merchants who actually knew their customers. Families could spend an entire Saturday shopping, teenagers hung out at the mall, and kids studied the Sears Wish Book carefully enough to create Christmas lists that made their parents wonder whether Santa offered financing.

Today, thousands of stores fit inside our phones. We can compare prices, order almost anything from the recliner, and sometimes have it sitting on the front porch the same day.

That's incredible convenience, but did we lose something along the way?

From Sears and JCPenney to malls, local stores, online shopping, and the mysterious algorithm that thinks buying one toilet seat means you want to start collecting them, Jeff takes a humorous and nostalgic look at how shopping changed from an experience into a transaction.

Were the old days really better?

Maybe not.

But there was something different about a time when shopping meant getting in the car, going somewhere, and making a day of it.

So how did we get from the department store to same-day delivery?

When did THAT happen?

Now here's a deal for my Old-er Guy Listeners.

If you enjoy a good cup of coffee, be sure to check out Afuera Coffee Co.. They feature specialty coffee sourced from sustainable farms in Central and South America.

And... You can save 15% on your order by using the promo code OLDERGUY.

Shop Afuera Coffee and get 15% off with code OLDERGUY

I do earn a commission when you purchase using my promotional link or code, and this helps support That Old(er) Guy Show.

Hey! I'd love to hear your thoughts, send me a voice note.

Are we actually smarter because we have Google—or have we simply gotten better at finding answers?

In this episode of That Old(er) Guy Show, Jeff Blair looks at how the internet has changed the way we learn, remember, and find information.

There was a time when answering a question might mean pulling an encyclopedia off the shelf, going to the library, or actually remembering phone numbers and directions. Today, we carry access to an almost unlimited amount of information in our pockets.

That's certainly progress. But there's a difference between having information, understanding information, and actually remembering it.

From Google searches and GPS directions to smartphones that remember everything for us, Jeff asks whether technology is making us more knowledgeable—or simply allowing us to outsource more of our memory and thinking to our devices.

And there's another problem: finding information is easier than ever. Figuring out which information is actually correct may be harder than ever.

Google can give us answers.

But can it make us smarter?

Maybe the answer depends on what we do after we hit “Search.”

It’s another look at modern life from That Old(er) Guy Show—where we look back, reflect and ask:

Were things better or worse? And... When did THAT happen?

Hey! I'd love to hear your thoughts, send me a voice note.

Remember when five bucks could actually buy lunch?

Not just part of lunch. Not a drink and maybe some fries. An actual meal.

In this episode of The Old(er) Guy Show, Jeff takes a nostalgic, and occasionally painful, look at what inflation has done to the everyday purchases we once took for granted. From hamburgers and coffee to movie tickets, gasoline, groceries, and restaurant meals, the numbers on the price tags have certainly changed.

There was even a time when the $5 Footlong became a cultural phenomenon. Subway introduced the nationwide promotion in 2008, and it became one of the most successful fast-food promotions of its era. Today, five dollars doesn't stretch nearly as far. One workplace-lunch index put the average lunch price at $14.73 in 2026.

So what happened? Is it simply inflation? Higher wages and operating costs? Changing expectations? Or have we slowly become accustomed to paying prices that would have made our younger selves put the menu down and head home for a sandwich?

Jeff looks back at what everyday things used to cost, what they cost now, and why those increases seem especially noticeable when you're old enough to remember the original price.

Because apparently the $5 lunch didn't disappear.

It just became the $15 lunch.

Topics in this episode: Inflation • Food Prices • Fast Food • Restaurant Prices • Grocery Prices • Gas Prices • Coffee • Cost of Living • Nostalgia • Everyday Economics • Then and Now

The Old(er) Guy Show: looking at today's world through the eyes of someone who's been around long enough to remember when five dollars was actually money.

Hey! I'd love to hear your thoughts, send me a voice note.

We’ve never had more ways to communicate—and somehow, we may be talking to each other less than ever.

In this episode of That Old(er) Guy Show, Jeff Blair looks at “The Lost Art of Talking to People.” Text messages replace phone calls. Restaurant orders are placed on screens. Self-checkouts replace cashiers. Automated voices handle customer service. And families and friends can sit around the same table while everyone is looking at a different phone.

Technology has made communication faster and more convenient, but has something important been lost along the way?

With humor, nostalgia and a little Old(er) Guy perspective, we look at what happens when efficiency starts replacing everyday human interaction—and why those seemingly insignificant conversations with cashiers, servers, neighbors and even strangers may matter more than we realize.

Maybe we don’t need another way to communicate.

Maybe we just need to start talking again.

Hey! I'd love to hear your thoughts, send me a voice note.

Common Sense has passed away.

After years of declining health brought on by warning labels, fine print, questionable decisions, unnecessary complications, and an apparent inability to ask, “Does this actually make any sense?" Common Sense has finally left us.

In this episode of That Old(er) Guy Show, Jeff Blair conducts a tongue-in-cheek memorial service for an old and trusted friend. We’ll remember a time when people were expected to think for themselves, accept responsibility for their decisions, and occasionally figure things out without an instruction manual, an app, or a committee meeting.

It’s part funeral service, part social commentary, and part affectionate roast of modern life.

So dress appropriately, silence your cellphone and join us as we pay our final respects to the dearly departed...

Common Sense.

May it rest in peace.

And who knows? Maybe someday we'll witness a resurrection.

Hey! I'd love to hear your thoughts, send me a voice note.

It seems like everything needs an app these days.

Want to park your car? Download an app. Order lunch? There's an app. Adjust the thermostat, buy a ticket, get a discount, check into a hotel—or sometimes just accomplish something that used to take 30 seconds? Apparently, there's an app for that too.

In this episode of That Old(er) Guy Show, Jeff Blair takes a humorous look at our increasingly app-dependent world and asks a simple question: When does technology make life more convenient, and when does “convenience” actually make things more complicated?

From restaurants and parking meters to appliances, tickets and businesses that expect a long-term digital relationship for a five-minute interaction, we'll look at what we've gained—and what we may have lost.

Technology can be great. But sometimes...

I just want to park the car.

Hey! I'd love to hear your thoughts, send me a voice note.

Do we really need a subscription for everything?

Hey! I'd love to hear your thoughts, send me a voice note.

Season 1, Episode 1 — “Newer Isn’t Always Better”

We’re constantly being told that newer means better—but does it really?

In the premiere episode of That Old(er) Guy Show, Jeff Blair takes a humorous and thoughtful look at our obsession with replacing perfectly good things simply because something newer has come along. From smartphones and electronics to appliances, cars and everyday products, we’ve gone from repairing and keeping things for years to upgrading, replacing and throwing them away.

Technology has certainly improved our lives, and sometimes newer really is better. But when did “old” automatically start meaning “obsolete”?

Join That Old(er) Guy for a little nostalgia, a few laughs and a look at whether progress always means moving on to the next new thing—or whether sometimes the old one was doing just fine.