50 So-So Dates Later, a Breakup Gets Unbroken

Denise K. Shull and William T. Long were married atop Aspen Mountain at the Aspen Mountain Club in Colorado.

Denise K. Shull tries to help bankers, competitive athletes and other clients improve their performance by getting in closer touch with their feelings.

As the founder of the ReThink Group, a consultancy in Manhattan, she advises traders and portfolios managers to analyze their fluctuating emotions, and even their childhoods, as carefully as they do the markets.

“Casual conversation doesn’t really exist with Denise,” said Craig Keslar, who has known her since she was the head cheerleader in high school. “It gets real deep pretty quick and that’s the fun of being around her.”

Lauren Smith, her best friend since eighth grade, said Ms. Shull rarely waffles when taking risks in her own life. “She just boldly decides — no angst.”

Ms. Shull, who is 58, married her high school sweetheart in her 20s; got a job as a systems engineer at IBM; divorced; moved to Aspen, Colo., to ski; and then earned a master’s degree in neuroscience at the University of Chicago. She planned to become a therapist, but became an equities trader instead.

By 2001, though, she was living in Manhattan and recovering from a broken heart.

“I had been dating somebody who broke up with me and vanished,” she said. Afterward, she struggled to meet new people. “I remember her complaining that on the Upper West Side, it was all strollers and dogs,” Ms. Smith said.

Ms. Shull joined Social Circles, a now-defunct networking company, and signed up for a group golf outing in July 2002. Each golf cart held two people and everyone scrambled for a partner. To Ms. Shull’s surprise, a slim economist, William T. Long, appeared by her side. “She seemed very confidant and very vivacious, very noticeable,” Mr. Long said. “I made a point of trying to get in the same golf cart as her.”

He met her three main requirements in a boyfriend. He had a graduate degree (a master’s in economics from Duke). He was in therapy. (“You gotta know yourself or you don’t have a chance,” she often says.) And, he had been divorced, in 1990. (“I wanted someone who knew relationships are hard,” she said.)

While her divorce was friendly — “We went to lunch together afterward,” she said — his was not. “Lots of drama,” said Mr. Long, who is 62 and grew up in Clemmons, N.C., surrounded by a large extended family. Ms. Shull, who was adopted, grew up as an only child in Akron, Ohio.

During their golf outing, she gave him her card, which he uncharacteristically misplaced. Friends describe him as organized and detail-oriented, unbeatable at word games, well-read and funny. At the time, he worked in New York City developing tax compliance software at KPMG, the accounting firm, and spent his weekends competing in road bike races. He lived in a studio apartment that was furnished mainly with bikes and biking equipment, all meticulously maintained.

Weeks later, he came upon her card and called. By then, she was preparing to move to St. Louis, partly to be closer to a half brother, John Kluge, who lived there. She and Mr. Kluge share the same biological father and first learned of each other’s existence in 1999 after Ms. Shull met her biological parents.

Before she left, they went on one date and found they have many of the same interests yet very different personalities. “Denise looks like an impulsive rock star to Bill’s chess-playing composure,” said Contessa Joret, a good friend of the couple.

They continued dating, traveling back and forth from New York to St. Louis and taking trips together. “She was easy to fly with, the easiest woman to travel with I’ve ever known,” he said. “She just has this laid-back attitude.”

Ms. Shull recalls first seeing Mr. Long’s apartment full of bikes. “I loved it!” she said. “On top of being cute and super smart, he’s a crazy good athlete in crazy good shape.”

In spring 2003, he persuaded her to move back to New York, which she did without hesitation. “She doesn’t have any problem picking up and leaving,” he said.

Over the next several years, the two lived in a high-rise building in Hell’s Kitchen; a house in Greenwich Conn.; an apartment on Manhattan’s Roosevelt Island; and another in Long Island City, Queens. In 2003, she founded ReThink, and in 2004 they acquired two Yorkshire Terriers. She taught him to ski and he encouraged her to go on long bikes rides with him, promising brunch somewhere along the way.

They even briefly discussed trying to have children together (neither have children from their first marriages) but decided against it. She regrets that. “What I know is that even in situations where there’s nothing that can be done about it, you admit to the whole spectrum of feelings and the regret becomes less debilitating,” she said.

The year 2012 was great for them. Mr. Long began working at ReThink, where he is now the chief of staff, and Ms. Shull’s book, “Market Mind Games: A Radical Psychology of Investing, Trading and Risk” (McGraw-Hill Education) was published.

But 2014 was terrible. They argued constantly, which upset Mr. Long more than Ms. Shull, who has a higher tolerance for emotional conflict. “I just didn’t feel like the relationship was working,” he said. “The hate seemed to be outweighing the love.”

They decided to separate and he moved to Charlotte, N.C., while she plunged into dating. She estimates she went on 50 dates in the months after their breakup, some arranged through Tinder. “In no time flat, in every situation, I would think, ‘They are not as smart as Bill, they are not as handsome as Bill, they are not as much of a gentleman as Bill,’” she said.

Mr. Long was not particularly happy, either. “The single life didn’t turn out to be as satisfying as I expected it to be,” he said. “It finally dawned on me, ‘Let’s work it out.’”

In the summer of 2015, he moved back to New York. He proposed to Ms. Shull a little over a year later, presenting her with a screen shot of a ring he thought she might like.

Organizing a wedding seemed like a daunting time commitment to Ms. Shull, who everyone describes as a workaholic, but getting married made perfect sense. “There may be times when we can’t stand each other but we can’t live without each other,” she said.

On April 12, the couple were married at the Aspen Mountain Club in Aspen, their favorite ski town. It was so windy that riding the gondola up to the club, atop Aspen Mountain, seemed more like a leap of faith than marriage.

The ceremony was small but not subdued. Eleven guests huddled together on the club’s outside deck, facing the Elk Mountains and shivering. The couple dressed neither warmly nor practically. “We are going all out, overboard, in terms of clothes and food,” the excited bride said. Mr. Long wore a morning suit while Ms. Shull appeared in a pink strapless organza and tulle gown, pink faux fur shawl, and a tulle veil that occasionally flew perpendicular. She was escorted onto the deck by Mr. Kluge, her half brother, who later said he was amazed to discover, upon first meeting Ms. Shull, that their feet and hands were nearly identical.

The ceremony began with Chloe Smith, a recent graduate of N.Y.U., singing “Truly Madly Deeply,” a song by Savage Garden, the Australian pop group. With no accompaniment, and as if she were addressing a lover rather than an audience, she slowly, plaintively sang, “I want to stand with you on top of the mountain/I want to bathe with you in the sea/I want to lie like this forever/Until the sky falls down on me.”

In Colorado, no particular authorization is required of wedding officiants so the couple chose Bill Smith, Ms. Smith’s father and a longtime friend, to lead them through the vows. He cried more than they did.

Afterward, everyone returned inside for a feast at one long table, amid the club’s mix of mounted antlers, abstract paintings, antique wood tables, cushioned banquettes and windows the size of highway billboards.

The bride, who is always monitoring her own emotions closely, later said: “I wasn’t the least bit nervous. I was just really happy. It was just so darn joyful.”

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