Around Valentine’s Day last year, Jenna Bush Hager, a host of NBC’s “Today with Hoda & Jenna,” embarked on a mission: to help her friend and colleague Elizabeth Harrington Leist, who goes by Libby, find romance.
“Jenna was reporting on love in the pandemic and how people were finding each other,” Ms. Leist, the senior vice president of “Today” and a senior vice president of NBC News, said. “I was looking to meet someone.”
Ms. Leist, now 43, had by then been single for years — “since my 30s,” she said. “I’d been fixed up with a million people who didn’t work out.” She had also recently been promoted from her previous position as a senior executive producer of “Today,” which meant she no longer had to get to bed early and wake up at 3:45 a.m. The lifestyle change opened her up to new dating possibilities. “I was transitioning and gaining a new perspective,” Ms. Leist said.
Though she had discussed her dating life with Ms. Bush Hager, Ms. Leist had never before been set up by her. To source potential suitors, Ms. Bush Hager contacted her fraternal twin sister, Barbara, and two friends. One of them was Emily Fisher, a fine arts photographer, who had met Ms. Bush Hager years ago through Willie Geist, the host of “Sunday Today.” Ms. Fisher quickly replied with a suggestion: Sayan Ray, her husband’s best friend.
Like Ms. Leist, Mr. Ray, 48, was experiencing a period of transition. In the summer of 2020, his previous marriage of 12 years ended in divorce. But he wasn’t as concerned with meeting new people. A father of two — his daughter, Shailey, is 12 and his son, Kieran, is 9 — Mr. Ray said that, following his divorce, “making sure my children were OK was my priority.”
His first reaction to Ms. Fisher’s overture was that he wasn’t ready. “Then she sent me a picture of Libby and I thought, she’s really nice looking and had a nice smile and I could tell she was a good person,” he said. “So I agreed.”
After Ms. Hager Bush introduced the two via email, Mr. Ray, the creative director at Harrison and Star, a health care marketing agency in New York, invited Ms. Leist on a date. She suggested they meet virtually, on Zoom, but he persuaded her to get together in person. “I wanted to get out of the house,” he said.
Their first date, on Feb. 21, 2021, began at Central Park, where they strolled around the reservoir. Coffee at The Consulate, a restaurant on the Upper West Side of Manhattan, followed.
As they talked, Mr. Ray said he found Ms. Leist to be “smart, solid and down to earth.” When he brought up his divorce, “she just listened,” he added. “I found that comforting.” Of her impression of Mr. Ray, Ms. Leist put it this way: “Jenna really delivered.”
Weeks later, they met for a second date on March 6. Ms. Leist traveled from her Manhattan apartment near Gramercy Park to spend the day with Mr. Ray, who had planned an itinerary of activities for the two near his home in Danbury, Conn.
The nine-hour excursion began with coffee and pastries at Hayfields Cafe & Florist, in North Salem, N.Y. Then came a two-hour walk. Afterward, they visited The Aldrich Contemporary Art Museum, in Ridgefield, Conn., and went shopping for antiques. Their last stop, in North Salem, was for dinner at Purdy’s Farmer & the Fish, Mr. Ray’s favorite restaurant.
“It was a lot to commit to, but it was sweet of him to show me” his area, Ms. Leist said. “He put a lot of thought into everything.”
Mr. Ray was thrilled to see Ms. Leist, whom he described as “a busy city girl in a busy job,” appreciate his slower-paced life. When the two became acquainted, he had wondered about the compatibility of their different lifestyles. “But showing her around and her being receptive to my area” made him more confident that a relationship would work, said Mr. Ray, who had begun to fall for Ms. Leist before their second date ended.
It took Ms. Leist three more outings to have a similar epiphany. Following their fifth date in late March, she recalled thinking, “Wow, I’m going to marry this man.”
That summer, Ms. Leist met Mr. Ray’s children at a Fourth of July barbecue hosted by Ms. Fisher and her husband, Murray Fisher. “I knew in my heart he was a great dad,” Ms. Leist said, “but now I got to see it.”
“It became very clear that Sayan had a whole life that existed before me and that I would have to figure out how to be a part of it,” she added.
As they continued to spend time with each other, slowly, a family unit formed. “I’ve always wanted children,” Ms. Leist said. “The more we got together, the closer I felt to gaining that.” Her weekends, which were previously spent going to SoulCycle and coffee with friends, as she put it, soon became dedicated to activities with Mr. Ray and his children.
Throughout their courtship, Ms. Leist and Mr. Ray always kept Ms. Bush Hager and Ms. Fisher abreast of any progress. “No detail was too small,” Ms. Leist said.
Their matchmakers appreciated every update. “There’s energy setting up two people, especially someone I love like Libby, who is funny, brilliant and a terrific friend,” Ms. Bush Hager said. Ms. Fisher described the pairing as “one of my proudest achievements.”
Though she had no hand in introducing the couple, Savannah Guthrie, a “Today” anchor and friend of Ms. Leist, also cheered on their developing romance. “We were texting at all hours of the night,” she said of herself, Ms. Bush Hager and Ms. Fisher. “Everyone was hanging on every development. It was like high school.”
Ms. Guthrie had tried to set Ms. Leist up many times, but never succeeded. “While giving birth I was checking out the anesthesiologist to see if he was good for her,” she said. “It became my mission,” she added, but “Jenna beat me to it.”
By the fall of 2021, Ms. Leist and Mr. Ray, who had begun discussing marriage months earlier, were both ready to take the next step toward it.
“It’s amazing how your mind can change,” Mr. Ray said, describing how he went from thinking “I’ll never get married again” to feeling like he couldn’t live without Ms. Leist. “I needed her in a way I didn’t expect,” he added.
Of their bond, Ms. Leist said, “It’s rare to find this, to have a deep trustworthy, honest connection with someone,” adding, “I never knew I could feel this way.”
Mr. Ray proposed that November at the New York City marathon, which happened to fall on his birthday. To execute the proposal, he had enlisted the help of Mr. Fisher and Mr. Geist from “Today,” who was running in the race.
About two miles before the finish line in Central Park, Mr. Fisher handed Mr. Geist a bag of Dunkin’ munchkins. Inside was also a small box containing a citrine and diamond ring. Mr. Geist then ran five blocks with the bag, before handing it off to Mr. Ray, who was waiting with Ms. Leist and a few friends near an entrance to the park.
To keep her from becoming suspicious, Mr. Geist said he was not only asked to deliver the bag to Mr. Ray, but also a line: “Someone in the crowd gave this to me, can you throw it out?”
After the handoff, Mr. Ray and Ms. Leist walked through the park, returning to a spot they had passed on their first date. Stationed nearby to take photos was Ms. Fisher, whose presence did not go undetected by Ms. Leist. “I didn’t get to finish everything I had to say because Libby saw Emily in the bushes taking photos and asked why she was there,” Mr. Ray said.
Despite being rushed, he still had time to get down on one knee and ask her to marry him. Ms. Leist immediately answered yes, and the two later celebrated their engagement at Sona, an Indian restaurant near Gramercy Park, with a small group that included the Fishers, Ms. Bush Hager and Ms. Guthrie.
On June 4, the couple were married at Grace Church in Utica, N.Y., before the Rev. Christine Williams-Belt, an Episcopal priest, and 145 guests. Mr. Ray’s son served as the best man and his daughter was a junior bridesmaid. Following the ceremony were a cocktail hour and seated dinner at Ms. Leist’s parents’ home in New Hartford, N.Y.
At the reception, Ms. Bush Hager and Ms. Fisher delivered a surprise speech, during which they read from a book they had created. Its pages were filled with the many text messages exchanged among their larger friend group during the couple’s courtship.
“There must be a thousand texts between all of us,” Ms. Bush Hager said, before quoting a message she had sent to Ms. Fisher on April 19, 2021.
“I really think this is it,” she said, adding, “and it was.”
On This Day
When June 4, 2022
Where Grace Church, Utica, N.Y.,
The Reception The bride’s parents’ home in New Hartford, N.Y.
High Notes The ceremony featured music and vocals from a pianist, tenor and opera singer. During the cocktail hour and dinner, guests were entertained by Troy Ramey, a singer, who performed “My Love Is Your Love” as the couple had their first dance. The evening concluded with a set from DJ Spider.
Just Kids At the dinner, the newlyweds sat at a table with 13 children, including Mr. Ray’s and those of Ms. Bush Hager and Ms. Guthrie. “We feel very close to all these children — they feel like family,” Ms. Leist said. “It was so joyful to watch them enjoy the wedding and it was a chance for us to connect during the wedding.”