Judah Schulman proposes to Toby Milstein on a beach on Long Island.
Judah Schulman proposes to Toby Milstein on a beach on Long Island.

For the 28-year-old NYC residents, the nuptials were the latest chapter of a 12-year love story that began on a volleyball court at the JCC of Metropolitan Detroit in West Bloomfield.

Judah Schulman and Toby Milstein got married Oct. 18 in a small outdoor ceremony in New York.

For the 28-year-old NYC residents, the nuptials were the latest chapter of a 12-year love story that began on a volleyball court at the JCC of Metropolitan Detroit in West Bloomfield.
The two first met after a volleyball match at the 2008 JCC Maccabi Games hosted by Detroit. Each said it was love at first sight.

Schulman, from Teaneck, N.J., was a 16-year-old basketball player for the Riverdale Y team. Milstein, from Scarsdale, N.Y., was a member of the Mid-Westchester volleyball team.

One of Schulman’s basketball teammates was dating a member of the Mid-Westchester volleyball team. That’s how Schulman ended up at Milstein’s volleyball match on Aug. 20, 2008, the day before her 16th birthday.

“I saw Toby playing and cheering with such passion and enthusiasm and thought, ‘Wow, this girl is so cute. I have to introduce myself to her,’” Schulman said. “So, I walked up to her after the match and did just that.”

What was Milstein’s first impression of Schulman?

“He was incredibly handsome,” she said. “I could hardly believe this tall, blond-haired cute guy was real. It didn’t take me long to realize the irony of having just met my own ‘Judah Maccabee’ at the [JCC] Maccabi Games. That may have been a little wink from above.”

Schulman said the two were “basically inseparable” at the JCC Maccabi Games after they met. They watched each other’s competitions, texted each other and met at evening activities.

Their relationship continued after they returned home, just before the start of their junior year in high school.

There was texting, phone calls, Skype dates and group get-togethers in New York City.

That was the best they could do in an era before smart phones and FaceTime calls.

“We were lucky to live decently close to one another [45 minutes apart], so we could meet up with friends in the city,” Milstein said.

The couple was together for three years, then scaled back to being close friends for six years as college, careers and Schulman’s gap year in Israel that included basic training with the Israel Defense Forces took precedence.

Judah Schulman and Toby Milstein at the 2008 JCC Maccabi Games hosted by Detroit.
Falling in Love

They began dating again in summer 2017.

“We came to the realization then that being close friends wasn’t adequate. We loved each other,” Milstein said.

The two were living together by the following summer, and Schulman proposed to Milstein on May 3 on a beach on Long Island after having several elaborate plans to pop the question scrapped because of the COVID-19 pandemic.

“I was clueless that Judah was going to propose to me that day. He totally surprised me,” Milstein said.

Longtime Detroit JCC Maccabi delegation head Karen Gordon learned about the engaged couple from the JCC Association of North America this summer and put together a box of memorabilia from the 2008 JCC Maccabi Games that eventually will get to the newlyweds.

The box is filled with a blue duffel bag, smaller white bag, copy of the opening ceremony video, pins and a poster designed by famed Brazilian artist Romero Britto.

Gordon said she’s aware of other couples that met at JCC Maccabi Games hosted by Detroit and later got married, but Schulman and Milstein are probably the first couple that came from different visiting delegations.

Besides meeting her future husband at the 2008 JCC Maccabi Games, Milstein became close with her host family, the Sandbergs.

“I remain in touch with my ‘host sisters,’ Erinn and Lauren. I visited Erinn at the University of Michigan a few years after the [2008] Maccabi Games,” Milstein said. “I’ll never forget the Sandbergs’ graciousness and the way I felt like I became part of their family.”

Schulman and Millstein live in the Greenwich Village section of New York City and are busy with their careers.

Schulman is a senior vice president at CAIS, a financial services and fintech company. He covers the Midwest for CAIS and is frequently in Bloomfield Hills.

Milstein is a second-year MBA student at Columbia Business School. She’s also an intern at the MetaProp venture capital firm that focuses on the real estate technology industry.

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