Brian Rosenberg hadn’t exactly planned on proposing to Jen Bilik behind the Hitching Post, a restaurant in Santa Barbara, Calif. (In retrospect, it was an amusing coincidence.) He also hadn’t planned on doing it in his car after dinner, which was parked in front of a sun-bleached turquoise Dumpster. And, moments after accepting, Ms. Bilik hadn’t planned on dropping the ring into a void from which personal effects are seldom recovered: the gap between the passenger seat and the center console.
Despite the parking lot and the Dumpster and the missing diamond — which was eventually located thanks to some desperate rummaging and an iPhone flashlight — the couple emerged newly engaged. The next day, they shot a re-enactment video for posterity. “We’re going to have a great life together!” Mr. Rosenberg says to the camera, throwing in a seven-letter adjective for emphasis. “We sure are!” Ms. Bilik responds from behind the lens, adding the same word.
The proposal came after a six-month romance that some friends and family considered whirlwind. But for Ms. Bilik, the founder and chief executive of the design and publishing company Knock Knock, and Mr. Rosenberg, a senior director of development for fund-raising at the cancer center City of Hope outside Los Angeles, it felt less like a hasty decision and more like a hard-won “about time.” As Ms. Bilik put it, “We earned each other.”
Ms. Bilik and Mr. Rosenberg, both 47, often wonder if they would have ended up together had they met 20, 10, even five years earlier, before either had found self-contentment. Ms. Bilik was raised in Berkeley, Calif., and when she was 21, she lost her mother to breast cancer.
“My mother was a quilter,” Ms. Bilik said. “I grew up quilting and sewing and making with her — that’s a large part of my identity and a lot of what Knock Knock grew out of.”
Mr. Rosenberg and his sister, Julie, were raised by their mother in Los Angeles. A little more than a month before Ms. Bilik and Mr. Rosenberg’s wedding, Julie died at age 43. “We were like twins,” Mr. Rosenberg said. “It was always just the two of us.”
Ms. Bilik’s 30s were consumed by 90-hour workweeks, which left little time for courtships. With the big 4-0 looming and no promising life partners in sight, she began in vitro fertilization. “I actually thought life might not be worth living if I didn’t have children,” she said.
After a year of unsuccessful treatments, Ms. Bilik started the process anew, this time with an egg donor. When the donor she chose fell through, she was surprisingly relieved.
“That’s what told me, ‘I think I’m going to be O.K. not having kids,’” she said. “Since I was 25, I had been dating to find my baby daddy. But I had done therapy and other kinds of personal work. I finally accepted that my mother had died, that my family wasn’t what I wanted it to be, that I wasn’t a skinny model. And I started to have fun. It was a new thing for me, not feeling like each person was my last best hope, but rather there’s more where that came from.”
At the same time, Mr. Rosenberg was on his own journey of self-discovery. “I’d considered myself relationship-phobic,” he said. “I was ready to become a monk. My whole thing is not being able to trust — I can’t take it if I go into something and give it my all and it doesn’t work out. After a lot of work, I got to a point where I was ready to open up. That’s where Jen came into my life.”
They met on OkCupid on Dec. 29, 2015. While Ms. Bilik (alias: WittyWarmWise) had been online dating on and off since the early aughts, Mr. Rosenberg (alias: drschauffhausen) only had to dip a toe into the quagmire before meeting his future wife. In fact, he received a message from Ms. Bilik five minutes after joining the site. “I got lucky,” he said with a smile.
She corrected him with a laugh: “You struck gold.” They were, according to the site’s algorithm, an 87 percent match.
At the time, Ms. Bilik had been sidelined by shoulder surgery, for a torn rotator cuff, and by a lumpectomy, to remove a cancerous mass from her breast. “I had this medical two months because my mother died of breast cancer,” she said. “I had to get tested for the BRCA gene mutation, and they thought they saw something in the other breast, but it turned out to be very early, low grade, all fine.”
To pass her recovery time, she put her shoulder — the good one, at least — into playing the field. And so she fired off the first missive to Mr. Rosenberg. “I didn’t think he’d write back to me,” she said. She was wrong.
The two set a date for Jan. 8, 2016, but on New Year’s Day, Ms. Bilik invited Mr. Rosenberg for a walk at Venice Beach with her golden retriever, Paco. “She said, ‘I’m in a sling, I’m wearing sweats, and I’m not wearing makeup,’” Mr. Rosenberg remembered. “And I was like: Yeah right, this is L.A. They always say that, and then they’re all done up. But she was in sweats, a sling, no makeup.” (“I hadn’t showered,” Ms. Bilik added for accuracy.)
Mr. Rosenberg was immediately stung. “When Jen is excited and happy, she looks like a 17-year-old girl,” he said. “I felt like I was 17 again when I met her.”
“I didn’t,” Ms. Bilik said. “I thought he was too nice.” After a flurry of phone calls and texts, they had their second date, in downtown Los Angeles. “He was so lovely every step of the way,” Ms. Bilik said. “I hadn’t had a lot of men be gentlemanly and kind. After that, it was game on.”
By Week 3, they had a woman named Candi Cane Cooper in their corner, who is not, as you might have reasonably assumed, a stripper by trade. Rather she is Ms. Bilik’s animal psychic. “When my dog Maisie was dying, Candi came to see her,” Ms. Bilik said. On a visit with Paco, Ms. Bilik asked Ms. Cooper to channel Maisie. “Candi said, ‘Let me see if I can get her,’” Ms. Bilik recalled. And then: “‘I’ve got Maisie.’”
“The only question I had was, ‘Are Brian and I going to fall in love?’” Ms. Bilik said. Maisie said yes. “In fact,” Ms. Cooper said, “Maisie says Brian has already picked out the engagement ring, one that belonged either to his mother or an ex-girlfriend, and it has a black pearl in it.”
Ms. Bilik wasn’t convinced. But that night, she regaled Mr. Rosenberg with the story. He was stunned. “Don’t take this the wrong way,” he told her, “but this afternoon I was thinking: ‘What if, after all this time, Jen is actually the One? I’m going to need to get an engagement ring.’” His mother’s favorite gemstone? Black pearls. Point for Candi Cane.
The next week, Ms. Bilik and Mr. Rosenberg exchanged I Love Yous. Their connection was fast and fierce and deep, which would be enough to scare most people in fledgling relationships — only Ms. Bilik and Mr. Rosenberg aren’t most people. “Middle-aged love moves fast,” Mr. Rosenberg said. “And even though we’re getting married late in life ——”
“We’re having our second marriage first,” Ms. Bilik chimed in.
Mr. Rosenberg said: “Right. It’s given me faith that there’s a beauty to the universe, because I feel like something planned it at a time when we’re both ready.” That readiness is what propelled Mr. Rosenberg to propose in front of a Dumpster on June 25 (in the end, he opted for something more blingy than a black pearl). As he said in the re-enactment video, “I couldn’t wait a minute longer.”
On May 27, the couple were married at the Inn of the Seventh Ray in Topanga, Calif., an open-air restaurant hidden among babbling creeks and a forest of ancient sycamores. Golden light pierced through the canopy, and the air was thick with the scent of jasmine and peonies, the favorite flower of Mr. Rosenberg’s sister. A huppah stood at the end of the aisle, its roof slung with a quilt made by Ms. Bilik’s mother.
A touching and humorous ceremony acknowledged the couple’s present joy and honored their past sorrows. One emotion could not diminish the other, and their coexistence was a reminder of what Ms. Bilik and Mr. Rosenberg may face in years to come. “You quoted to me once that it’s the partner who’s good in the emergency room and the bedroom who’s the real prize,” Ms. Bilik said to Mr. Rosenberg in her vows. “Which means I’ve won the lottery.”
“I regret not finding you when I was younger,” Mr. Rosenberg said. “You are the best chance I ever took on love. You’re the one thing I ever did right.”
Rabbi Zoë Klein took Ms. Bilik and Mr. Rosenberg through their I Dos. Afterward she alluded, in a somewhat sanitized way, to the proposal re-enactment the couple had posted online, asking them, “Are you effing sure?” The bride and groom, both radiant, vigorously nodded their heads.