Brian O’Rourke, who has worked at O’Rourke’s since age eight, marries a love for food and community at the Middletown diner.

O’Rourke’s Diner, situated at the north end of Main Street, is more than just a local breakfast joint. Certainly it has a familiar style; there are innumerable railroad-car diners all over America, boasting flashy neon signs and retro curved aluminum roofs. But upon entering O’Rourke’s, you notice the ancient Irish family crest in tile on the floor: two prancing lions on a yellow shield, surrounded by the words “Céad míle fáilte” (100 thousand welcomed). As you are led to your table, you pass by the emergency exit door, painted to be a chalkboard on which the quote “No one has ever become poor from giving” is written neatly. You slide into your wooden booth by the wall of windows and your waitress bustles by to drop off a plate of dense, house-baked chocolate chip bread at another table. She offers you a menu, which features a striking black and white photo of the quintessential façade, credited to the manager, Derek Trafton. Most tellingly, you see an unexpected number of familiar smiles between the happy diners and Brian O’Rourke, head chef and owner, who regularly visits tables to greet his friends.

O’Rourke, now in his mid-sixties, is a large presence in the cozy diner, but not only because of his tall stature. He floats from table to table, like a honeybee between blossoms, engaging with his customers, who are a combination of Middletown residents and Wesleyan students. Many of them are regulars. With comfortable eye contact and a particularly strong handshake—a result of hand-strengthening exercises that are part of his martial arts practice—O’Rourke conveys his calm energy and genuine interest in interacting with those who will be enjoying his cooking.

O’Rourke wakes up at four o’clock every morning to begin his routine. He practices Tai Chi and yoga; then, over a meticulously assembled cup of coffee, he completes his correspondences. By 7:00 a.m., when he makes his way to the diner, he has balanced his energies and is ready to open up the kitchen. He is constantly planning ahead, following through on his belief in the mantra of the “five P theory”: proper preparation prevents poor performance.

“Apply it to every part of your life,” O’Rourke said.

A look inside his walk-in refrigerators proves that he sticks with his mantra: metal shelves are always packed neatly with a wide variety of food. Breads, 90 percent of which are freshly baked by him or his staff, line the shelves, along with the freshest ingredients he can find. Marked bowls covered in plastic include peach and green tomato salsa, fried green tomatoes, sweet potato mash, harvest coleslaw with apples, cabbage and kielbasa, pumpkin waffles, and hot cider. These dozens of ingredients are combined in unimaginable ways to form O’Rourke’s seasonal specials.

O’Rourke puts as much care into his relationships with his staff as he does his food, viewing his diner as the home of a family. Surf Faulkner, now a waitress, recalls being welcomed in. After dating Trafton, the manager, for six weeks, she was offered some work.

“I thanked Brian after my first shift and he interrogated me about my relationship with Derek and made sure that I was in it for the long haul,” Faulkner said. “Brian didn’t want to hire me if I wasn’t sure that I would ultimately end up with Derek. He didn’t want Derek or himself to be hurt. […] He was looking out for everyone.”

Now, eight months later and still happily with Trafton and the diner, Faulkner feels that O’Rourke is not just a boss.

“[He is more of a] quirky uncle, a madman all his own, who looks out for ‘family,’” she said.

For the past few months, he has been learning Spanish so he can speak with two new kitchen hands. However, whenever he says something in Spanish, he expects them to reply back in English. He put it simply, and with a smile warmed by his sense of community:

“Our team is good.”

Though Friday, Saturday, and Sunday are the diner’s busiest days, there is never a slow day at O’Rourke’s. On weekdays, you can still find the place nearly full, but there is enough time behind the scenes for the cooking staff to prepare the specials for the coming weekend, when the lines regularly stretch down the sidewalk. During Family Weekend or Homecoming at Wesleyan, the extra long wait does not deter the dedicated, since students want their parents to get a taste of the best food around.

“It’s a constant thing,” O’Rourke said. “It never stops.”

Currently, O’Rourke works four to five days a week. He spends much of his free time outdoors, bird-watching or practicing Arnis, a Filipino martial art involving a stick. The latter is beneficial to the rehabilitation of his foot, on which he had two surgeries last June. In his downtime after the surgery, he worked on putting together a cookbook, “Breakfast At O’Rourke’s,” which Wesleyan University Press will be publishing in the coming months.

“I’m not a great storyteller, but I’ve got the stories to tell,” O’Rourke said.

In 1941, after working at several restaurants, John J. O’Rourke, Brian O’Rourke’s uncle, settled on the current location and name of O’Rourke’s Diner. During World War II, John served in mess hall on the Galapagos Islands, returning in 1946 to carry on what he’d started. In fact, he brought the current restaurant home with him, having the prefabricated unit trucked up from New Jersey, a common practice at the time. It looked about the same as it does now, though it lacked the current addition that expanded the kitchen and three additional tables.

Brian O’Rourke began working at the diner when he was eight years old. After his day at grammar school, he would cross the busy intersection to the diner, where he would wait for his dad to pick him up on his way home from work. Soon, he was running down the steep stairs to fetch food from the fridge and peeling hundreds of pounds of potatoes for his uncle. In high school, he worked 40 hours a week and became a crucial element in keeping the restaurant open 24 hours a day (which, alas, it no longer is). After a semester at Central Connecticut State University, he realized that he would rather be at the diner. He came back to work six days a week as a short order chef, eventually extending to specials. Though he recognizes the importance of a college education, he has “a Ph.D in Dinerology,” and the education is both extensive and ongoing.

“It touches everything,” he said.

At the diner, O’Rourke has seen someone die of a heart attack and has also saved lives. When one woman fell to the floor, he provided mouth-to-mouth resuscitation and brought her back to life. She still comes to the diner, thanking O’Rourke every time.

Having worked at the diner for nearly six decades, O’Rourke has seen how Middletown has changed.

“It was a great little town,” he said. “Now it’s a pretty good city.”

In the 1960s, O’Rourke recalls, Middletown was a bustling hub of trade and employment.

“It was like a Navy town every Sunday night,” he said.

On Main Street alone, there were 12 barbershops, 12 pharmacies, five car dealerships, three movie theaters, seven Italian markets, and several sweatshops where Italian women made dresses and coats. Middletown also had a popular pool hall, where high-profile games acquired hundreds of spectators, while another site was said to have hosted some of the best games of craps in the country. O’Rourke has observed the polarizing socioeconomic split between the north and south ends of Main Street. Now, O’Rourke’s serves as a monument to times past, before the urbanization and rise in commuter jobs severed Main Street in two.

Since becoming the official owner of the diner in 1977, O’Rourke has made the diner into a culinary hotspot. He is never content with the status quo. His extensive travel and experiences as a chef around the world have flavored and inspired his cooking techniques, but primarily in the form of new concepts rather than recipes. In New Orleans, where he worked under renowned chef Paul Prudhomme and at the Commander’s Palace, he fell in love with New Orleans-style seasonings and learned that each dish has layers of flavor: what you smell, the initial taste, the aftertaste, and what lingers in your mouth even hours after a meal. In Ireland, he gleaned that fresh, local ingredients are key to any dish. While spending time in Aruba, where seafood abounds, he saw that one could prepare a main course in endless iterations.

The culmination of these travels and a life of cooking is “Brian’s Breakfast,” fixed on the menu. It represents the ethos of the diner: O’Rourke will prepare a meal, often in multiple courses, based on the ingredients in his kitchen and his imagination. No two are identical, and even the waiters do not know what to expect. But rest assured, you will be receiving an exquisite meal, for this is where O’Rourke shines.

The idea for the menu item came about one morning when O’Rourke was cooking for family. Someone wished to be surprised, and was obliged, but when a second meal was requested, there were not enough ingredients. O’Rourke was not concerned.

“I had enough of this,” he said, tapping his heart, “and that’s the main ingredient.”