Dating apps get a bad rap, but on rare occasions, they do lead to love.
That was the case for Haley Cashman (now Levine) and Benjamin Levine, who met on JSwipe, a Jewish dating app, in 2017.
Ben was living in Brookline, working at a private equity company called HarbourVest Partners, and Haley was living in the North End, working at Mass General Hospital. They were on the app because they were both looking for Jewish partners – Haley grew up in Marblehead, going to the former Temple Israel (now Shirat Hayam), and Ben grew up going to Temple Beth Torah in Holliston. Both have close relationships with their families, and maintaining that connection to their Judaism in their future partners was a priority.
“We were both looking to find our person,” Haley said.
Their first date was in April of 2017, at Lolita in Boston’s Back Bay. The to-be couple schmoozed over margaritas and sangria at the bar, and noshed chips and guac while they spoke. It quickly became clear that there was something more there than just both being Jewish.
“We clearly had so many similar interests and values,” Ben said. “That was the initial spark in our relationship.”
“We both value our friends and family, we both have a really strong work ethic, and obviously being Jewish is really important to us,” said Haley.
While they were at the restaurant, someone approached Haley when she went to the restroom and told her that she and Ben were really cute. “How long have you been dating each other?” the stranger asked. A surprised Haley said, “We’re on a first date! I don’t even know him! “It was funny that someone thought we had been together for so long,” she said. Perhaps it was a sign – at the very least, it was good intuition by that stranger. Because they kept seeing each other after that, building a relationship in the cradle of the area where they both grew up. They explored all that Boston has to offer – kayaking on the Charles, Red Sox games with each other’s families, even just walking around the city together.
“We had a lot in common in our outside world,” Haley said. “We like to explore and have fun, and do things outside of our work life, too, having a good balance.”
For Ben, the sense of comfort he felt with Haley’s family was particularly important for their relationship. “Spending time with Haley’s family, it became clear to me that our families were really cut from the same cloth,” he said. “It felt really easy to integrate into the Cashman family.”
When the pandemic hit, they decided to move in together, getting an apartment in Brookline in 2020. About a year later, on a beautiful autumn Sunday, Ben proposed.
“I had a feeling it was coming, but Ben did a really good job at making it really special, and a surprise,” said Haley. He had told her that they were going to get brunch with their sisters and their husbands, and they went on a walk by themselves on the Charles River Esplanade beforehand. Ben proposed on one of the docks there, and afterward, both of their families surprised them and came together to celebrate with a picnic on the Esplanade. It was Sept. 19, 2021.
The wedding itself took place nearly two years later, at the Wychmere Beach Club in Harwich Port. “Cape Cod is a really special place to Ben, and has now become a special place to me,” said Haley. Ben grew up spending summers on the Cape with his grandparents near Wychmere, and while the couple were dating, they often took trips to the beachy area.
“We wanted to get married in the summertime, by the water, on the Cape,” Haley said.
On July 16, 2023, 170 guests arrived at the venue, which was bedecked with white florals and a general air of light elegance. Ben and his six groomsmen wore tuxes, and the eight bridesmaids wore black gowns of their choosing. Haley wore a gown from Ceremony, a bridal store in Newton Centre, which she described as “a one-shoulder, flowy, whimsical dress.”
They held a ketubah-signing before the ceremony with a small gathering of close family and friends. “It was a very special moment … to have those people present for the ketubah signing,” said Haley.
The ceremony took place at 6 p.m. inside, facing big windows overlooking the ocean. The chuppah had Lucite on the sides with white florals on top. Two tallit, one each from Haley and Ben’s grandfathers, were strung above the couple. During the ceremony, they were wrapped in the tallit of Ben’s late father, Alan, and for the Sheva Brachot, they had seven aunts and uncles come up and read the traditional blessings. Haley put on her bubbe’s gold wedding ring, and the Kiddush cup they drank from was from Ben’s bar mitzvah. The couple read each other vows in front of those gathered.
Ben’s cousin, Providence-based Rabbi Elan Babchuck, officiated. “He found ways to incorporate more meaning and integrate a lot of different family relics,” said Ben. “[He found] a way to really make it so special, so we could honor some of our late family members, but also just make it very authentic. We were really lucky.”
“Elan did such a great job of highlighting our story but also connecting it back to Judaism,” Haley said. “He kind of talked about how Ben and I are two old souls at heart.”
An indoor-outdoor cocktail hour came after the ceremony, followed by a reception in the same space, overlooking the beach. “We had quite the hora [dancing] celebration,” Ben said. “Which was one of the special moments. It was all just really beautiful.”
Next month, the couple will be traveling to South Africa and Mozambique on their honeymoon, taking their spirit of adventure outside of the United States for the first time in their relationship.
“Creating new memories with Haley and growing together is what I’m most looking forward to,” Ben said. “I’m just excited to share in special moments, new opportunities, and challenges together.”
“Ben and I really love to try new things and challenge each other,” said Haley. “That’s what we’re most looking forward to.”
Haley now works as a registered nurse at Brigham and Women’s Hospital, and Ben is a senior associate at HarbourVest Partners. They live in Roslindale. Θ