For a Bus Driver and a Salon Manager, a Detour on the Path to Parenthood

One of the things Jason Robert Santiago loves about his job as a New York City bus driver is that behind the wheel, he can get a lot of thinking done.

Last fall he figured out how he was going to propose to Tiffany Antoinette Roller, for example. Years before that, he worked through a fleeting concern that she might be obsessed with him. Lately he has been mulling over tips from regular passengers about how to make a marriage last.

“One of them was telling me that if you want it to survive, you have to learn to let go of the little things or you’ll end up resenting the person,” he said. He and Ms. Roller already have experience tackling a big thing. Since 2023, they have been trying, unsuccessfully, to conceive a child.

Ms. Roller and Mr. Santiago, both 36, are native New Yorkers. In early January 2020, he saw her picture on Instagram and agreed with the app: She was someone he might want to connect with. “I saw she was a nice-looking girl and thought, I’ll take a shot,” he said. He messaged her to introduce himself. For a week, they ping-ponged messages. When he started lobbying for a date, he made sure she knew he would need at least a day’s notice to get himself ready.

“I remember him saying, ‘Let me know if you’re free on a Friday night because I’ll have to get a haircut,’” Ms. Roller said. Her job as a general manager at the Paul Labrecque Salon & Skincare Spa, on East 57th Street in Manhattan, had made him self-conscious about his looks.

The daughter of a retired N.Y.P.D. policeman, Ms. Roller grew up in Bensonhurst, Brooklyn, with a younger brother, Jason Roller. Their parents, Louise Bruno-Roller and Thomas Roller, moved in with her maternal grandmother, Antoinette Bruno, when she was a baby. In 2002, Ms. Roller’s mother died suddenly on Christmas Day from an infection brought on by strep throat. Ms. Roller was 14; Jason, now a New York City policeman like their father, was 7. Shared grief brought the family closer. “At home there were always a lot of laughs,” she said. “Jason and I were both good kids and we all respected each other.”

In 2014, grief over the loss of a family member came for her again when Ms. Roller’s grandmother, who had become more like a mother, died after a stroke. “That was even more of a trauma than when my mom died,” she said. “It was the hardest time of my life.”

A year later, she was hired as a receptionist at Paul Labrecque.

By then, she had completed an associate degree in psychology from the College of Staten Island and was looking for a change of scenery.

“I had always worked local jobs,” often at the front desk of spas and salons, she said. “I needed to get out of Brooklyn.”

Commuting to Manhattan to Paul Labrecque carried with it a sense of sophistication: “It felt like a big-girl job,” she said. In 2017, Ms. Roller moved out of the house in Bensonhurst and bought a condominium on Staten Island.

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Mr. Santiago was born in Bensonhurst and grew up in Great Kills, Staten Island. He and his two sisters, one older and one younger, were raised partially by their grandparents after his mother and father, Alison Heilweil-Santiago and Rogelio Santiago, divorced.

When he graduated from Susan E. Wagner High School, he took a few online college courses, but nothing compelled him toward a degree. For years, he bounced from job to job. “You name it, I tried it: I cleaned carpets, I did flood restoration, I delivered pizzas.” He credits his mother with helping him land what he called “a solid city job” in 2015 with the Metropolitan Transportation Authority; she had signed him up for the tests that would eventually qualify him as a bus driver.

On Jan. 9, 2020, Ms. Roller told Mr. Santiago to book himself a haircut, setting in motion their first date the next day at the Hop Shoppe, a Staten Island gastro pub. Because he drives the rush-hour express bus from Staten Island to Manhattan and back every weekday, she felt safe letting him pick her up at her condo in his Jeep. Her confidence in him not being the reckless type was not initially a two-way street.

“She got in the car with a drink in her hand,” Mr. Santiago said. “I thought, maybe she’s a little too wild for me.” Later that night, she told him the drink was a way to keep her nerves at bay. Once they started talking, she knew she didn’t need it.

Mr. Santiago was then living with his grandmother, Eileen Gaffan-MacArthur, on Staten Island. “Some women might be turned off by a man in his 30s living with his grandma,” Ms. Roller said. “But he was caring for her after a fall, and I respected him for that. I had cared for my grandma before she passed. It felt like a nice connection.”

Because Ms. Roller’s job was at a salon with an upscale reputation, Mr. Santiago hadn’t counted on Ms. Roller being someone he felt he could joke with. “You would think she would be snobby or high maintenance,” he said. “She wasn’t that at all.” That night, they kissed at a red light on the drive home. His haircut, in a style Ms. Roller called a “tape-up” — short on the sides and longer on top — had been met with her approval.

Before the onset of Covid that March, they were spending so much time together — including on Mr. Santiago’s bus, which Ms. Roller started going out of her way to catch on 55th Street after work — that Mr. Santiago worried things were moving too fast. “He sat me down and said, ‘I really like you, but I think we should pump the brakes,’” Ms. Roller said. “For a week or so there was this weirdness. I didn’t know how to act.”

“I didn’t want to get sick of her,” he said. “I thought, maybe it’s a bit much. Maybe she’s obsessed with me.” When he contracted Covid later that spring and moved into her condo to quarantine away from his grandmother, his ambivalence shifted. “Tiffany took care of me,” he said, and they got along great. “That was it for pumping the brakes.”

Mr. Santiago made his move to Ms. Roller’s condo permanent last summer. By then, he knew he wanted to marry her. But he also knew marriage wasn’t her top relationship priority.

“Tiffany wants to be a mother more than she wants to be a wife,” he said. Soon after becoming a couple, they agreed they wanted a baby. “From the beginning, Jason and I were very open to the idea of whatever happens, happens,” she said. By early 2023, after a series of fertility tests, they were beginning to accept that, for them, conceiving might require medical intervention.

“I was never anti-marriage,” she said. “I just always thought Jason and I will probably have kids, then go down to City Hall with wedding bands and legalize everything.” Mr. Santiago upended that plan on Oct. 26, with a surprise proposal. He had been planning the moment on his bus route.

During a vacation in the Bahamas, he wrote, “Will you marry me?” in the sand. “I never thought Jason could be that thoughtful,” Ms. Roller said. She also didn’t expect getting engaged to lift the fog of disappointment over their trouble conceiving. But it did, at least partially. “I started thinking, maybe God has a different plan for us, and we’re supposed to get married first. It’s been such a happy time for me.”

On March 20, Ms. Roller and Mr. Santiago were married by Shunya Togashi, an officiant at the Staten Island Marriage Bureau, on what would have been Ms. Bruno’s 100 birthday. Fifteen guests attended, including Ms. Roller’s brother and father and Mr. Santiago’s mother and grandmother.

Ms. Roller wore a short white dress with black stockings and an elbow-length custom veil inspired by an old photo of Priscilla Presley, a favorite celebrity. Mr. Santiago wore a gray suit he had shopped for at JCPenney with his mother.

“It felt intimate but fun,” Ms. Roller said shortly after the wedding, which was capped by guests showering them in bubbles in lieu of the traditional rice. Mr. Santiago was happy to be able to call her his wife. “Just seeing her smile the way she did — she’s the best,” he said.

Both left the marriage bureau hopeful about the future. “We’re excited to be moving on to the next phase together,” Ms. Roller said. “Becoming parents, I think, will be just around the corner.”

On This Day

When March 20, 2025

Where The Staten Island Marriage Bureau

Cheers and Chopsticks After the ceremony, the couple and their guests went out for Chinese food at Oriental Plaza, a favorite Staten Island restaurant. “I wanted lo mein, dumplings and a Diet Coke,” Ms. Roller said. “As New York as it gets.” On May 9, they will hold a larger reception for 50 guests at the Staten Island location of Patrizia’s, an Italian restaurant.

Benefits The couple hopes being on the same insurance policy as a married couple will help their fertility journey. Mr. Santiago’s state health benefits may cover a majority of the costs of intrauterine insemination or in vitro fertilization costs, Ms. Roller said.

Jewel of a Passenger One of Mr. Santiago’s regular passengers is a jeweler. Days before the wedding, “he met me at his stop with a ring sizer so I could figure out what size my wedding ring will be,” he said. “It was pretty special.”