A Fifth Grade Crush Revisited

Christopher William Anderson knows firsthand that being a marriage therapist is no guarantee your marriage won’t break up.

His own first marriage ended in divorce more than a decade after he started counseling couples in 1979 in his home state of Texas. When he and Joan Elizabeth Winter married in Round Top, Texas, in July, he had a clearer understanding of the struggles that can make sturdy relationships falter.

Mr. Anderson and Ms. Winter, both 70, met as fifth graders in 1963, at Will Rogers Elementary School in Houston. A few days into the school year, Ms. Winter was transferred to Mr. Anderson’s class because her own homeroom was overfilled. She found a seat next to his.

“Immediately we were connected,” said Ms. Winter, a former high school English teacher and school administrator who now works part time in administration at Collins Ostrum, an Austin, Texas, law firm. “He was the sweetest boy, the most beautiful boy, with beeswax in his combed-back hair.”

Mr. Anderson had admired Ms. Winter from afar since first grade, when she caught his eye in the Will Rogers hallways. “Back in the day, kids held hands when they were walking to class,” he said. “I would look at her across the way, holding somebody else’s hand, and get jealous.”

When she sat down beside him in Ms. Faust’s class as a 10-year-old, the instant connection hit him, too. “It’s hard for me to describe, but even in all the years we didn’t see each other she had a place in my heart. I thought about her.”

Mr. Anderson carried Ms. Winter’s books on walks home from school through fifth and sixth grade; a long-lost love poem he wrote her, “Joanie, the Beauty of Texas,” is an unforgotten treasure. But at the end of sixth grade, Mr. Anderson’s family moved to a different part of Houston, in a different school district.

The two still occasionally saw each other — Ms. Winter babysat for Mr. Anderson’s cousins, and a date after high school that ended with a good night kiss on her family’s front porch may or may not have happened (Mr. Anderson remembers it, Ms. Winter does not).

By the time both enrolled in college at the University of Texas at Austin in 1971, the connection had frayed. “It felt like we were walking down the same street, but on different sides,” Mr. Anderson said. The streets they would walk down as graduates, and later as adults with families, diverged much farther.

Ms. Winter, whose parents, Frances and Cecil Winter, died of cancer three years apart in the 1980s, grew up with two brothers in Houston. Allen Winter, her older brother, was born with a brain injury and lived in a state hospital for much of her childhood. She and Mark Winter, her younger brother, now care for him at his group home in Rosenberg, Texas.

After she graduated with a bachelor’s degree in English from the University of Texas at Austin in 1975, she later enrolled in graduate school there, earning a master’s degree in communication in 1984. She stayed in Austin after college, teaching and working in marketing at a science museum. In 1987, she married her first husband. Before they divorced in 2004, they had three children, Hayden, William and Patrick Dunham, all born in Austin.

Mr. Anderson didn’t wait as long to start a family. In 1974, a year before he earned his bachelor’s degree in history from the University of Texas at Austin, he was married. “I was 21,” he said. “I thought I knew everything.” It would take several years before he realized he didn’t.

Mr. Anderson has a master’s degree in clinical counseling from Our Lady of the Lake University in San Antonio, Texas, in 1979. A year later, when his son Paul was born, he was working as a therapist in Abilene, Texas, specializing in couples and families. By the time his daughter, Sarah Haverly, arrived in 1983, he was reconsidering his career choice. “I was a young dad, and because I was paid per hour and there were only so many hours in the workweek, I was feeling the stress and anxiety of knowing that I was only going to make a certain amount of money,” he said.

To increase his income, he gave up therapy and became a stockbroker at the brokerage firm Rotan Mosle in Austin. Up until then he didn’t have much interest in finance. “I didn’t know a stock from a bond, literally,” he said. Money was not considered a polite topic of conversation in the family he grew up in. “I would ask my dad about it and he would say, ‘It’s none of your damn business.’”

Mr. Anderson’s father, Harry W. Anderson Jr., died in 2011; his mother, Ann McElroy, lives in Austin. His older sister, Julie Anderson Shephard, lives in Houston, and his brother, Reece Anderson, in Austin.

Options trading at first propelled Mr. Anderson financially. But in the mid-1980s, he started bleeding money in speculative investing. Within a few years, “I ended up broke, foreclosed on, in divorce court and suicidal.” Speculative investing, he said, was a fancy word for reckless betting. “I had a gambling addiction.”

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Years of therapy helped him recover from that addiction. It didn’t mend his family, though. A brief reconciliation with his former wife after they separated in 1987 brought him to Chicago, where she had moved. By the time they divorced in 1990, he had relaunched his career as a therapist there. A trickle of clients seeking help for gambling problems turned into a flood. “My personal journey equipped me with tools I got to use to benefit other people,” said Mr. Anderson, who continues to treat gambling addicts in Texas.

Mr. Anderson was living alone in Evanston, Ill., when he decided to move back to Austin in 2014. “I loved Chicago, but it was not my home,” he said. A preliminary investigation into what dating might look like in his former stamping grounds led him to Match.com. There, he found the profile of his grade-school sweetheart, Ms. Winter. “I thought, oh my gosh,” he said.

Ms. Winter had been on Match for a few years when Mr. Anderson messaged her through the dating app in December 2014. She didn’t take her Match dates too seriously. As a single person, “I was pretty content,” she said. “But I was 60 and just hoping to meet someone who would be a great partner.” She hadn’t seen Mr. Anderson since her 1987 wedding and only briefly spoke to him then — her ex-husband had invited him. In his message, Mr. Anderson asked if she could meet for coffee while he was in town house hunting over the Christmas holidays.

“I said, ‘Well, sure,’” Ms. Winter said. He was flying in on Christmas Eve. Instead of coffee, she offered to pick him up at the airport. She and Mark had been visiting Allen just before he landed. Mark drove her to the airport.

Mr. Winter recalls an en route conversation about whether Ms. Winter should greet Mr. Anderson with a kiss. “I encouraged her to plant one on him,” he said. She did. “And it was pretty electric,” Ms. Winter said. “Mark is always pushing me toward the good things in life.”

In the two weeks they had been talking on the phone before Christmas Eve, Mr. Anderson’s onetime schoolboy infatuation solidified into love. At the airport, “it wasn’t just, ‘Oh yeah, I know who she is.’ It was, ‘I know you,’” he said. “There was something very powerful in that kiss.”

For the next 10 months, while Mr. Anderson navigated moving his home and his practice to Austin, their relationship grew long distance. In the fall of 2015, he moved into the cottage Ms. Winter had been living in for a decade. “But then it became, this town ain’t big enough for the both of us,” she said, with a laugh.

In 2016, he rented a place down the street. They still live apart a few days a week — Ms. Winter is often in the cottage, and Mr. Anderson lives primarily near Round Top, where he bought a 20-acre horse farm in 2017. “The LAT scenario is a dreamy system that offers us flexibility,” Ms. Winter said of their living-apart-together arrangement.

Mr. Anderson, the reformed gambler, is not completely risk averse. In July 2016, on a vacation to Italy, he asked her to marry him at a romantic cafe in Assisi. Her response was essentially, “Yes, but not now.” For him, marriage felt like an important threshold for them to step across. But for her, the prospect jogged feelings of wariness. “I knew I wanted a partner, but I didn’t know about marriage,” she said. “Chris had to redefine it for me, and he gave me a lot of space to explore that. He said, ‘We don’t have to have rigid roles.’”

Six years later, she called him with a proposal of her own. In the fall of 2022, Mr. Anderson and Ms. Winter joined St. Cecilia’s Episcopal Church in Round Top. A priest there, the Rev. William Miller, asked them to lead a course on healthy relationships for couples. “It was about getting to know all the areas in marriage that were crucial for couples to get past,” Ms. Winter said. Being Mr. Anderson’s co-facilitator came with a sense of irony. “I looked at all these other couples, and they were married and we were not, and I thought, something’s wrong with this picture.”

On Nov. 1, 2022, she downloaded a marriage application from the Travis County website. “I filled it out with the clear intention of being married that day,” she said, in the local courthouse. Mr. Anderson had to convince her to wait until their families, including their children and six grandchildren, could gather in Texas.

On July 8, Father Miller, an Episcopal priest, married them before 65 guests at St. Cecilia’s. Ms. Winter, who has been raising honeybees with Mr. Anderson on the farm since 2018, declared herself the day’s queen bee: “I don’t like attention, but I relished the role,” she said.

In her cream vintage lace dress and cowboy boots, clutching a bouquet of local sunflowers, she met Mr. Anderson, who wore a light linen suit, for an exchange of traditional vows at a sunflower-filled altar. Their children, some who had met for the first time at the wedding, sat on either side of them. Each gave a reading. The bride’s younger brother, Mark, delivered a homily.

Sunlight poured through the church windows as the couple recessed to the Beatles’ “Here Comes the Sun,” with guests singing along. Ms. Winter called “This Love Will Carry,” by the Scottish singer Dougie MacLean, a sentimental favorite. “That beautiful song is all about us,” she said.

On This Day

When July 8, 2023

Where St. Cecelia’s Episcopal Church, Round Top, Texas.

Something Sweet This summer the couple harvested 20 gallons of honey, giving most of it away. Jars with custom labels were passed out as favors at a reception at the Grand Fayette Hotel in Fayetteville, Texas, where guests were abuzz over a cake decorated with confectionary bees and sunflowers.

Backward and Better Ms. Winter’s wedding dress was custom made at a Round Top boutique. When she picked it up the day before the wedding, she tried it on backward and liked the fit better. So that’s how she wore it. “Sometimes you have to work with things,” she said.

A Brother’s Blessing Mark Winter, the bride’s younger brother, who knew Mr. Anderson as a child, is thrilled to call him brother-in-law after so many years. “They are the two most prepared people in the world to get married,” he said.

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