Simon Kyu Seung Yi likes to jokingly credit himself with Dr. Gem Marian Manalo’s academic success. After all, he was her SAT coach during the summer of 2005 — reviewing math tips like the mnemonic PEMDAS rule order of operations and building vocabulary through Mad Libs.
“This guy must be a huge nerd,” Dr. Manalo said she recalled thinking, one of three students in the course. “Who spends the summer tutoring students for the SATs?”
She was 15, and about to enter her sophomore year at University Liggett School, a private school for prekindergarten to Grade 12 in Grosse Pointe Woods, Mich., where she grew up.
“I’d call on Gem because she always had all the answers,” Mr. Yi, now 38, said.
He was a 19-year-old rising sophomore then at the University of Michigan, from which he eventually graduated with two bachelor’s degrees: one in business administration, and the other in economics.
“He felt so much older than me,” said Dr. Manalo, now 34, who began her freshman year at Michigan the semester after he graduated.
It was there that she earned a degree in art history and biology, followed by a master’s degree in medical science from Boston University and a medical degree from Wayne State University in Detroit. She is now an anesthesiologist at Midtown Endoscopy & Surgical Center in Manhattan.
In 2023, she moved to New York from Boston, and the week following a two-month break from online dating, she matched with Mr. Yi on Hinge.
The message “‘Simon likes you’” showed up in her email, she said, at the end of January 2024.
Once she saw his profile — his photo, and that he graduated from Michigan — she put together who he was.
“The age difference was not big anymore,” she said.
She had no romantic expectations. “At least I’d have another friend in New York with someone I kind of know.”
Mr. Yi is a founder and head of growth at Myosin.xyz, a company that helps with the expansion of blockchain technology. He had returned a couple of weeks earlier after spending three months setting up its Lisbon office.
“It just hit me,” he said. “She was one of my students.”
They met “serendipitously” online, he said, using a good SAT word, and met a day after Valentine’s Day in 2024 at the SoHo location of La Compagnie Wine Bar, where he ordered a Portuguese Douro red wine.
He then got down to business, and asked her outright if she wanted children, as he did. The bartender, approaching, and within earshot, made a face, she said, and told them “‘I’ll come back later.’”
Dr. Manalo, taken aback, considered the possibility. “Once I was 30 and still single,” she said, “ ‘Maybe kids are not in the cards.’ He made it seem possible.”
They later parted with a platonic hug, and exchanged numbers.
When he texted that evening, Dr. Manalo suggested meeting the next week at Libertine, a restaurant in the West Village, where she already had a reservation. (She often made random reservations for two at restaurants, then asked a friend to join her.)
It was then his idea to meet at Little Island park in Manhattan before dinner to watch the sunset, and afterward listen to jazz at Smalls, a nearby club.
That evening, when he mentioned he traveled a lot for work, and would be spending the next three months in Korea, she grew concerned.
“I’m not trying to do a long distance,” she said. “How is it going to work?”
They later took an Uber to her apartment in NoMad, and kissed good night. He then walked to Penn Station to catch a train to Syosset, N.Y., where he was staying with his parents.
“I figured out my priorities over the next few weeks,” he said.
Not only did Mr. Yi, from a Korean background and fluent in the language, soon decide to spend only a month there, but he invited her to join him in Seoul.
“I thought it meant a lot for him to ask me to meet him halfway around the world,” Dr. Manalo said, and agreed to go.
They then began dating seriously, and by July 2024, they went ring shopping.
“He brought out the best in me,” she said.
In August, she received shocking news — her father was diagnosed with a serious illness. As a result, they discussed getting married sooner.
Later that month, one Friday after work, Mr. Yi, suggested they take along their watercolors for a picnic in Madison Square Park. At the park, he painted an oak tree and she focused on the skyline toward 23rd Street. “OK, stand up,” he finally said, and got down on one knee and formally proposed.
On March 29, the Rev. Jerry Brzezinski, a Roman Catholic priest, officiated before 22 guests, at Saints Peter & Paul Jesuit Church in Detroit.
“It meant the world that my father walked me down the aisle,” she said, “and we shared a father-daughter dance” later when they celebrated at San Morello, a restaurant nearby in the Shinola Hotel.
At the restaurant, a three-piece jazz group performed, and a two tier-cake included a topper of her cockapoo Cooper.
“Timing was so important,” Mr. Yi said. “PEMDAS, the order of operations is all there.”
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