Christina Vance and Greg Winick dressed up as superheroes for their first date at a 2017 Halloween party in Totowa, N.J. She went as Batgirl, he as Batman. A good pair for couples, the costumes also alluded to the strength and resilience that brought each to that moment.

“Before we began dating, life had kind of beaten us up,” said Ms. Vance, who teaches English to sophomores and juniors at Mount Olive High School in Flanders, N.J. “We were both in marriages filled with pain and suffering.”

“From where both of us were coming from, it felt more like the first day of the rest of our lives together than it did a first date,” she said.

Ms. Vance and Mr. Winick met in September 2010 at Central Middle School in Parsippany, N.J., where Mr. Winick teaches English to seventh-graders, and Ms. Vance, then a single mother with a 1-year-old son, worked as a student-teacher in his classroom.

That arrangement ended within weeks, when Mr. Winick received a phone call from a doctor telling him that his wife, Cathy Winick, and their son Jesse Winick, then 15, required life-threatening surgeries that were scheduled in the coming days. The two were suffering from Von Hippel-Lindau syndrome, a genetic disorder which causes cysts and tumors to grow in the body.

“It was hard to believe, hard to accept,” said Mr. Winick, who immediately took a leave of absence to comfort his son and his wife.

“Cathy was diagnosed with this thing in her early 20s,” said Mr. Winick, now 56. “At that point in time, she had made it through 36 surgeries, and my son had also spent a lot of time in hospital rooms.”

Both his son and his wife pulled through their respective surgeries and, four months after taking his leave, Mr. Winick returned to his classroom. But Ms. Vance, now 36, had by then left her student-teacher position to complete her studies at Montclair State University in New Jersey, which she graduated from in 2011 with a bachelor’s degree in English and a teaching certification.

When he was not teaching, Mr. Winick began pouring most of his energy into writing a memoir, the first of several books on a variety of subjects that he would self-publish. A graduate of William Paterson University, where he received a teaching certification, he holds two master’s degrees, one in educational leadership from Marygrove College in Detroit and another in education from Montclair State University, where he also received a principal certification.

Soon after her surgery, though, his wife started experiencing other complications. They led to a brain hemorrhage, which ultimately contributed to her death in January 2013, after the Winicks had been happily married for 20 years.

The next year, in October 2014, Ms. Vance married her son’s father. By then, the pair had a second child and was expecting a third.

But their relationship, she said, was flawed from the start. “Things were bad from the beginning. I was in a bad place in life when we started going out and ignored the signs,” said Ms. Vance, who added that, after the couple married, “things gradually became worse” and they eventually separated in December 2015.

“It became a volatile situation,” she said of their relationship by the time the two separated. “I had to get out of there.”

Months earlier, in September 2015, she returned to Central Middle School as a sixth-grade English teacher and reconnected with Mr. Winick. The two began advising the school newspaper together, an activity that she said eventually led them to talk every day.

Ms. Vance and Mr. Winick, who had each experienced different kinds of pain, soon became aware of the other’s plight. The more they spoke, the more they realized how much they had in common.

In 2017, Ms. Vance filed for divorce from her husband. That June, she left her job at Central Middle School after moving with her three children to Dingmans Ferry, Pa. in April. There, she filed for sole custody. When her day in court came, a judge in Pike County, Pa., granted her full custody of the three children without spousal visitation.

Around that time, Mr. Winick had begun to write a blog called “30 Days of Mindfulness.” After drafting entries, he would send them to Ms. Vance for editing before he posted them. The blog became the basis for his second book, “The Plausible Path to the New Possibility,” self-published in February 2017, and a motivational speaking course the two started offering later that spring.

By the fall of 2017, Mr. Winick and Ms. Vance had turned a romantic corner. On Oct. 28, 2017, the pair donned their Batgirl and Batman costumes for their first date, which Ms. Vance said began with a kiss that made her know she had found someone special in Mr. Winick.

“Those costumes definitely gave us a psychological boost at that time,” Ms. Vance said. “That night we had such a great time, which seemed like a sign of better things to come.”

After getting to know one another as friends, each understood the other needed time to ease into a new relationship. Ms. Vance’s divorce became finalized in June 2018, and that Thanksgiving, more than a year after their first date, she introduced Mr. Winick to her children, Nicholas, now 11, Sophia, now 10, and Braden, who goes by Brady, now 7. From then, the two began to date more frequently.

With Ms. Vance’s help, Mr. Winick self-published another book, “A Poker Story,” in May 2020. Months later, on Oct. 20, 2020, they became engaged when he surprised her with a proposal in the form of a guitar performance.

“He made a parody to Kenny Rogers’s ‘The Gambler’ on the spot,” she said. “He ended it with the line, ‘And then he bought her a ring and he’s gonna give it to her right now.’”

The challenges each overcame to get to that moment, Mr. Winick said, made it even more memorable. “For the two of us the whole journey felt a bit surreal,” he said.

In February 2021, the couple moved in together with Ms. Winick’s three children, splitting their time between their two homes in Dingmans Ferry and Woodland Park, N.J. They were married on Nov. 4, 2021, at the Westmount Country Club in Woodland Park. Paula Jensen, a Universal Life Minister, officiated before 170 guests, most of whom were vaccinated.

The couple’s children took part in the ceremony. Jesse Winick, now 26, was Mr. Winick’s best man. Ms. Vance’s son Nicholas was a groomsman, her daughter Sophia was a flower girl and her son Brady was the ring bearer.

“We imagine careers, getting married, having families and a happily-ever-after,” Ms. Jensen said in her remarks. “Unfortunately, our fantasies don’t include twists, turns, dead ends and road blocks.”

“Greg and Christina faced all of that and more,” she added. “Now here they are today, together and very much in love, no more obstacles in their way.”

On This Day

When Nov. 4, 2021

Where Westmount Country Club in Woodland Park, N.J.

Thanks, Nan The bride was primarily raised by her maternal grandmother, Carol Kocis. Known as Nan, she died in May 2015 and might have had a hand in the couple reconnecting, according to Ms. Vance. “When I couldn’t find a job after graduating from college, I kept wishing that my grandma was still around for me to lean on. Then I came home one day and checked my answering machine, and someone was finally offering me a job” at Central Middle School, she said. “I hung up the phone, looked up at the calendar and a chill ran up and down my spine. It was grandma’s birthday.”

Growing Family In December 2021, Ms. Vance filed to terminate her ex-husband’s parental rights and she and Mr. Winick began the process for him to adopt her three children. “With them around, I just have so many more interesting things to do,” Mr. Winick said. “It truly gives me something wonderful to live for.”