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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.
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