Long before they became a couple, Dorothy Kaplan Zoller and Stephen James Epstein had begun to double date.
Mr. Epstein’s first wife, Rozanne Epstein, had been a high school friend of Ms. Zoller’s first husband, Joseph Zoller. After college, they all settled in Chicago and became fast friends.
Living just a few blocks from each other, the couples socialized often, sharing dinners and celebrating graduations, weddings, and bar and bat mitzvahs. The Zollners’ two daughters, now both in their 50s, and the Epsteins’ three children, also all now in their 50s, played together as kids. Some of the two couples’ grandchildren — 10 between both — went to the same summer camp.
In 2018, Ms. Zoller, 79, who goes by Dottie, lost her husband of nearly 54 years after a long illness. Mr. Epstein, 83, who goes by Steve and holds a law degree from Northwestern University, walked her through the painful process of settling his estate.
The following year, when Mr. Epstein’s wife died suddenly in 2019 after almost 55 years of marriage, he reached out to Ms. Zoller for help navigating his loss.
“How do you get out of bed in the morning?” he asked.
“I understood exactly what he meant,” Ms. Zoller said.
Over lunch one day the two commiserated. Ms. Zoller was just a few steps ahead of Mr. Epstein in what she referred to as the “unchartered territory of grief.” Their conversations from then were intimate and sometimes accompanied by tears. When one felt overwhelmed, the other served as a rock.
“We were lucky we didn’t have bad days at the same time,” Ms. Zoller said.
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As their time spent together continued to increase, the shroud of grief around both started to lift. Soon, they began attending lectures, concerts and family events as a pair. Though the two had been friends for decades, growing closer allowed each to learn new things about the other.
A retired editor and writer, Ms. Zoller, who goes by Dottie, began her career in 1964 as a researcher at Playboy magazine before she and her first husband co-founded a marketing and communications company. A lawyer who is now semiretired, Mr. Epstein, whose parents immigrated to the United States from Ukraine and Poland, started his own legal practice with the assistance of his first wife.
Shortly after the pandemic arrived in March 2020, he moved into Ms. Zoller’s home in Highland Park, Ill., where the two still live. Around that time, she out loud floated a question to Mr. Epstein that both had previously thought, but never said.
“Correct me if I’m wrong, but has something changed here?” Ms. Zoller asked.
She was speaking to the fact that, when their spouses died, neither was looking for love. But by then, both had recognized that the ease and comfort they shared as companions in grief had morphed into something more tender.
“It’s bittersweet, we wouldn’t be together if we hadn’t lost the people we loved most in the world,” Ms. Zoller said of her unlikely relationship with Mr. Epstein. “But you never know when the music is going to stop and we are still here and we are happy.”
Once both knew that they wanted to spend the rest of their lives with each other, they decided together to get married and told their children earlier this year.
On May 15, the couple were wed at Makom Solel Lakeside synagogue in Highland Park by Max Weiss, Mr. Epstein’s son-in-law and a rabbi at Oak Park Temple in Oak Park, Ill. Their 39 family members in attendance, all of whom tested negative for Covid before the event, included the bride’s and the groom’s children and seven of their 10 grandchildren.
Ms. Zoller walked down the aisle carrying a nosegay of lily of the valley blooms, her grandmother’s favorite, from her own garden. At the close of the ceremony, guests called out wishes for the couple’s future, which included good health, long life, travel, and of course, happiness.
Afterward, the newlyweds and their family gathered at the couple’s home for champagne and dessert, including cupcakes made by a friend of the bride.
“This is a marriage of two optimists,” Mr. Epstein said. “We bring experience to this. We know how to do marriage.”