As I walk through the door of Harry's Char Broil Dining Lounge, a server says hello and asks if I want a cup of coffee.

In 2017, the question seems as anachronistic as being asked if I think we'll beat the Russians to the moon. I nod instinctively, saying please.

There's no follow-up questionnaire, no choice of Americano, macchiato, latte or soy foam. Instead, the server walks through the dim space, past frayed blue vinyl booths and mounted photos of fishing trips, to a percolator that's been here since there were only two kinds of coffee, regular and decaf (which they don't have). An older man sits on a stool, gazing out the window. A father and daughter in the booth adjacent to mine dig into bacon and eggs.

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The only giveaway that Harry's is under different, younger ownership is the television – once tuned to CP24, it's now playing Viceland.

It's darker too, says Norm Hernandez, who cooked at Harry's for 16 years until it was sold last year. "With us, we had the lights on," Hernandez recalls. "People like to see their food."

But compared to Grant van Gameren's other businesses, the diner might as well be in an alternate universe. When you walk into Bar Raval, for example … well, you can't walk in at night. The packed pintxo/tapas bar has a doorman. The room looks like a Doctor Strange spell carved out of mahogany. A cocktail menu lists ingredients you've never heard of (flinture, phonezone, byrrh), and drinks cost more than anything on the menu at Harry's.

It's been nearly 10 years since van Gameren rose to prominence as the chef of the Black Hoof. Through a variety of partnerships (he's started a management company, Overbudget Inc., that oversees many of the operations, but they're all separately owned), van Gameren has many pieces of an eclectic pie: the Spanish-themed Bar Isabel and Bar Raval, El Rey Mezcal Bar and cocktail bar Pretty Ugly.

Banquet Burgers, stacked with cheese, bacon, lettuce and tomato are one of the favourite dishes at Harry’s. Glenn Lowson/The Globe and Mail

He and his partners have just taken over the former location of Mitzi's Sister (in Parkdale, like Pretty Ugly and Harry's), with plans to turn it into an Eastern European restaurant serving sausages, smoked fish, perogies, goulash and cold-climate wines. "I've been trying to perfect my cabbage roll recipe," van Gameren says.

And a space at College and Bathurst has just been secured for a long-planned Mexican restaurant that will only cook with fire (a refusal to use gas in the kitchen delayed things). He's also launching a catering company, Victor Dries (rhymes with Victor Fries, alias Mr. Freeze, the Batman villain).

Considering the variety of international cuisines, ambitious menus and swanky decor in his portfolio, the Harry's move is an odd one. It's a traditional diner with no room for $68 Galician cockles on the menu. And it's at the southwestern corner of Parkdale, down a side street, with an entrance off an alley. You have to be looking for it to find it. But it was also van Gameren's hangout.

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During his 20s, when he was a broke cook working at Il Fornello, Canoe and Lucien, van Gameren lived just up the street and would go to Harry's for breakfast. For the past couple years, owner Tommy Petropoulos, who opened the restaurant in 1968 with his brothers George and Sam, had been attempting to sell it. A six-month demolition clause means that if the building's owners decide to tear down the building, the restaurant will have to close without much notice.

But Nate Young, who was chef de cuisine at van Gameren's Bar Isabel, had diners on the brain. "After working at Enoteca, Grace, Isabel, you're always cooking food from another region," Young says. "Somebody else's food. A diner is something that's a little bit closer to my heart."

I met Young in 2010 when I was hosting a short-lived series of dinners for up-and-coming chefs to cook for an audience of established restaurateurs, ostensibly to get critical feedback. At the time, Young was the sous chef at Grace Restaurant. For an audience that included van Gameren and Jen Agg (the Black Hoof, Rhum Corner, Grey Gardens and, back then, van Gameren's business partner), Young nervously plated scallops with rhubarb purée, a cherry tomato terrine, tagliatelle with anchovies and a lamb saddle with mashed potatoes. The jury noted how down-to-earth Young's cooking was, compared with other dinners at which Colin Tooke (Grand Electric) had three types of fish in his fish course, Amanda Ray (Biff's) prepared a carrot consommé, Fan Zhang (Mr. Flamingo) made foie gras popcorn and Brandon Olsen (La Banane) presented a blood-flavoured custard.

Justin McIntosh works the grill at Harry’s in Parkdale on February 15, 2017 Glenn Lowson/The Globe and Mail

The guests loved Young's modest cooking, but questioned if restaurant customers would go for such unflashy cuisine.

That's what the 29-year-old Young loves about the diner experience. "It comes without pretense. I love the culture, the look of any diner, the idea that you can sit for an entire afternoon, drinking coffee or reading the newspaper. Working with or for Grant, everyone wants to know what you're going to do next. And at a diner people are just expecting what you have."

While burgers, fries and fried eggs are modest in the context of big-league chefs, raising the standards for diner food comes at a price.

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"If you go to most diners, a lot of what you're getting is frozen, preportioned, precooked food," says Young, who brines his own peameal bacon and makes his own red and green chorizo burgers. "Making all that stuff from scratch costs money."

A couple items at Harry's exceed the average price of $10. But, as the menu declares at the top, "all taxes included – cash only." So an eight-ounce, hormone-free skirt steak with fries at $18 is still less than the average $16 cocktail at Raval.

Quality aside, the burger ($11.50 with fries) costs more than it did last year, when Petropoulos was charging less than $6.

Justin McIntosh layers up burgers with a mix of traditional and exotic flavors at Harry’s. Glenn Lowson/The Globe and Mail

Shortly after the diner reopened in September, someone spray-painted "hipster makeover!" on the wall outside.

"I knew that people were going to be upset," van Gameren says. "It's a Parkdale staple."

The Harry's renovation cost one-sixth of what he spent on Raval. And most of it was spent on the kitchen, on equipment that can be removed if the landlord exercises the demolition clause. But the investment isn't without risk.

"Parkdale is interesting. Because you can't just do anything there, like on College," van Gameren says. "You always have to keep in mind what Parkdale wants, then what you want and how to fuse the two together. Locals are your clientele. If you get tourism, great. But at the end of the day, you're feeding people from around the neighbourhood."

Harry's presented a chance for van Gameren to diversify and for Young to pursue his diner dreams. But the main challenge, as it is when taking over any existing business, was customer retention.

"They were all hesitant to even step foot in the door," Young says. "And then a few weeks after we opened, one of the old regulars, Frenchie, died. We had the memorial here and it really broke the ice. Because they met me and saw that the people that took over aren't the monsters they were afraid of. There was a lot of fear from people in the neighbourhood that we were going to have burgers on the menu for $20. But I lived across the street for six years and I was more than aware of what the place was. That was the most attractive part."