Ms. Steinberg, 37, met Mr. Klein, 52, in March 2007, when she was a law student at Tulane University in New Orleans. Had she been less inclined to breach the boundaries of the New York neighborhood where she grew up with two sisters and her parents, Richard, a lawyer, and Nancy, a real estate agent, their paths may not have crossed.
“It was spring break and I came home to visit,” Ms. Steinberg said. “My sister and I went to a party, and then we went to Niagara,” a downtown club. Downtown night life wasn’t foreign to Ms. Steinberg even though she had an uptown pedigree: In high school, her best friend Melissa Broudo recalled, “we were nice Jewish girls but we thought we were punk rockers. We would go hang out in the East Village every weekend, and we worshiped Sid Vicious.”
Mr. Klein, who was easing out of his music career after playing big festivals like the Warped Tour with Libertine, was D.J.ing at Niagara. Ms. Steinberg started talking to him. By the end of the night, he had her phone number and they were making plans to meet the next day. The differences in their backgrounds — he dropped out of high school when he was 14 to join a band, she studied classics and anthropology at Williams College before earning a master’s degree in Latin American Studies at Tulane and enrolling in law school there — barely registered.
“I pretty much spent the rest of that spring break, which was my last year in law school, with him,” she said. “I don’t know if I thought it would lead to anything serious, but we connected.” When she was back at law school, a long-distance relationship took shape. “We were on the phone a lot. I was thinking, There’s definitely something there.” She based her decision to move back to New York after earning her law degree on that seductive something.
Mr. Klein, lanky and heavily tattooed, was just as eager to resume his face-to-face relationship with Ms. Steinberg despite what he called the “Lady and the Tramp” scenario. Though he had few stable relationships in his life — he and his mother, Wendy Klein, were only sporadically in touch with Ms. Harry when he was in his 30s despite her occasional pop-ins at his punk shows, and he was estranged from his father, a onetime New York cabdriver, after his parents divorced in the 1980s — he felt the potential for something lasting with Ms. Steinberg.
“No one is going to believe these words came out of my mouth, but I feel like it was pretty electric right off the bat,” he said.
At first, navigating the social gulf between their families wasn’t an issue. Ms. Steinberg’s parents had moved to Scarsdale, N.Y., a few years earlier, and Mr. Klein’s mother had moved to Lake Owassa, in northwestern New Jersey. Mr. Klein’s schedule was an excuse to avoid Scarsdale. “He was always out at night D.J.ing or playing music, so there was no real opportunity for him to meet my parents,” Ms. Steinberg said. But by the time they planned a trip to Belize a few months into their relationship, a Steinberg family tradition disrupted the cocoon they were building around themselves.
“When somebody in my family is going to leave the country, we always have dinner first,” said Ms. Steinberg, now a lawyer practicing litigation defense at Kennedys CMK in New York. Mr. Klein covered his tattoos with a long-sleeved shirt and headed to what Ms. Broudo called the Steinberg’s “schmancy suburb” in Westchester County.
“When I got there, I was like, This has to be phony. It was this stereotypical perfect American house with a beautiful family. I was like, Why is no one screaming at each other and breaking things?” Mr. Klein said. “My perception of family was chaos.”
The Steinbergs, to Mr. Klein’s surprise but not Ms. Steinberg’s, expressed few reservations about the relationship. “My parents are pretty open,” she said.
He said he felt uncomfortable for a long time. “I probably spent the first three years I knew them wearing long-sleeve shirts,” Mr. Klein said. “But at the end of the day they saw that their daughter was in love. And they accepted it.”
In 2009, Ms. Steinberg and Mr. Klein moved into the one-bedroom apartment they still share in Greenpoint. In 2011, Ms. Broudo’s husband, Aaron Broudo, a lawyer, approached Mr. Klein about starting a music club. Their first venture was an outdoor night bazaar in Brooklyn. That evolved into BK Bazaar, which has been featured on the opening credits to “Saturday Night Live” and functions as kind of a community center, combining music, food, bars, art, karaoke and mini-golf.
As Mr. Klein’s business acumen developed, his desire to marry Ms. Steinberg grew too. “I knew around six years ago I wanted to marry her, but I’d been completely consumed by work,” he said. His mother’s death after a long illness in 2014 also required some reckoning. Despite his messy childhood, they had been close.
After a search, Ms. Harry resurfaced to help him grieve. “I had lost her phone number like 12 cellphones ago,” he said. But he knew she would want to know Ms. Klein had died. “Debbie and my mom grew up together and were always the bad girls together at their high school” in New Jersey. “She was my first babysitter.” For Ms. Harry, he said, the news hit hard. “She was like, ‘I wish I could have done something.’”