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 of 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…


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