When Sofia Vaninna Franklyn was going through a breakup in 2021, her friend Sarah Powell at Maclynn International, a matchmaking agency, persuaded her to sign up.
“I never thought about matchmaking in that way,” Franklyn said. “I thought it was kind of this older style” of dating.
Franklyn went on a date through the agency and ghosted the “very kind man” from that date, she said, because she got back with her ex. But then they broke up again the following year, and Franklyn didn’t hear from the service again until 2024. “I thought that maybe I was banned,” she said.
Her matchmaker’s suggestion was John Benjamin Messamore, who wasn’t having much luck finding the one on dating apps. A friend also recommended the matchmaking service to him, and he decided to give it a shot.
In interviews with matchmakers, Messamore explained the type of person he thought he would connect with: someone who works in law, accounting or finance and would understand his world. (He has worked in finance his entire career.) But his dates with people who fit the bill went “wildly unsuccessfully,” he said. The agency tried something different.
Before a work trip from his home in London to New York in September 2024, his matchmaker asked him if he would like to meet an entrepreneur in Manhattan named Sofia. On the way to their first date at the bar inside Fouquet’s, a hotel in Manhattan, he looked her up.
“I was like, ‘Oh my God, this might go horribly wrong,’” Messamore said. On paper, they were entirely different. She’s a podcast host; he works in private equity. Her life is public; his is not. Plus, she had gotten wrapped up in quite a bit of drama.
That drama was her public split with her former best friend and college roommate, Alex Cooper. In 2018, the two debuted “Call Her Daddy,” a podcast about sex, dating, culture and life in New York. It quickly became a hit with millions of listeners. When their contract with the distributor, Barstool Sports, came up for renegotiation, a messy disagreement over the terms left Cooper as the podcast’s sole host in 2020. Since then, Franklyn has created her own podcast, “Sofia with an F.”
Despite his initial worries, Messamore, 39, called it “the best date of my life.”
“We just connected on so many levels we didn’t expect,” he said. They discovered they both grew up in middle-class families — she in Salt Lake City, Utah, and he in Fayetteville, N.C. — and both speak Spanish.
“We talked about books, philosophy, religion, whether free will exists,” he said. As their conversation unfolded, so did their connection. “It’s not that we agreed on everything,” Franklyn, 34, said. “It was just synergy, and it was just chemistry — chemistry you can’t really describe or explain.”
They also talked about their dating goals. He was looking for a life partner. She said her next boyfriend would be her last.
The earnestness of their first date was a change for Franklyn, who said she had “made a living off the dating game,” and often treated dating like a game. “In the past, my whole thing would have been: ‘Don’t ever let the guy catch you saying that. Try to just be casual and fun, and maybe that can be intimidating.’”
“But then I grew up,” Franklyn said, “and I did some healing and some soul searching. And I was like, I don’t want to play a game anymore.”
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That night, they messaged about a storybook Franklyn grew up reading called “The Missing Piece Meets the Big O” by Shel Silverstein. It made him feel closer to her, and he thought she could really be the one. But he also said he had a feeling that “she’s probably somebody who could be a little flaky.”
“Probably lots of guys are trying to take Sofia out,” he said. “So I was really worried that I wouldn’t get that second chance to meet her.”
In the event that she tried to cancel their second date, he purchased the book as a gift so he could at least drop by and give it to her.
As they were trying to set up a second date, Franklyn indeed was being a bit flaky. Even though she really liked him, she’s a homebody, she said. So Messamore resorted to his backup plan and asked to drop by her apartment in the East Village to drop off the gift. She met him downstairs, and they sat at the bus stop and talked.
“We had this outrageously forward conversation,” Messamore said. They acknowledged that pursuing something serious would mean a long-distance relationship down the line.
He returned to London, and they were texting and having long calls. Date number three was in Paris in October after he invited her on the spur of the moment. They walked around Paris, hand in hand.
“She brings out a side of me that was lacking,” he said. “I’m not the most emotional person on earth, and there’s just a connection and a life that she brings out of me that no one else ever has.”
Part of that comes from Franklyn’s emotional intelligence rubbing off on him. “And then there’s just this familiarity,” he said. “We love some of the most random same things. Like, we’re obsessed with the Postal Service and Death Cab for Cutie. Movies, TV shows, music, fast food preferences.”
Their fourth date was in Miami later that month and their fifth was in New York in December, when he stayed with her for a week. Messamore surprised her with a mini Christmas tree for her apartment. They went to F.A.O. Schwarz, watched rom-coms on her couch and said “I love you” for the first time.
They began seeing each other once a month, meeting in destinations like Mallorca and Barcelona in Spain, and Zermatt and Saint Moritz in Switzerland. But it was during their quieter moments together that their relationship deepened. “Where the real connection was formed was watching TV on this couch, getting takeout and being homebodies together,” he said.
Franklyn has kept her home in New York, and Messamore has kept his in London. The two hope to start a family. “I did want to do it in the traditional way of getting married, and then starting a family,” she said.
Franklyn started off in her career challenging traditions in the dating and relationships space — by offering a form of female locker room talk on “Call Her Daddy” that discussed sex as openly as men do while embracing dating, pleasure and having fun.
But, she said, “People can have growth, women can have growth, opinions can change. When I started having a very public career, I was 25, and that was a long time ago.”
During that time, she was also jaded about love, she said: “I mean, hi, my memoir is called ‘Daddy Issues.’ I would go into relationships with some stuff from my past.” But Messamore, she said, was patient and understanding with her.
“Daddy Issues” will be published by Simon & Schuster in November. In it, she reflects on her time on “Call Her Daddy,” the falling-out with Cooper and the journey of reinventing herself since. Franklyn graduated from the University of Utah with a bachelor’s degree in economics. Messamore graduated from the University of Virginia with a bachelor’s degree in finance and Spanish.
In August 2025, he proposed over room-service pancakes and a bottle of rosé at Airelles La Bastide, Gordes in Provence, France.
On July 31, before their wedding festivities began, the couple were legally married at Villino Rubini, a villa in Brunate, Italy, with two witnesses present. Brandon Bear Bangs, an ordained minister with a Utah wedding officiant service called $99 Weddings, officiated via Zoom from Utah. Because the officiant was in Utah, where the couple obtained their marriage license, the remote ceremony was legally solemnized under Utah law.
Later that day, the couple held a welcome dinner outdoors in Piazza Roma in Argegno, Italy. The next day, they hosted activities at the villa for their guests, including pasta making, wine tasting and watercolor painting.
On Aug. 2, they held their wedding celebration at Villa Pizzo in Lombardy with about 140 guests. Shelley J. Whitehead, a relationship coach who had guided Franklyn and Messamore through an intensive couples retreat before their engagement, led the ceremony.
“There’s kind of nothing more beautiful about this life than finding your person,” Franklyn said. “I can’t even believe what’s coming out of my mouth right now because never have I ever spoken like this.”
On This Day
When July 31, 2026
Where Villino Rubini in Brunate, Italy
Riva Boat After the Aug. 2 ceremony, Messamore and Franklyn, who wore an archival Vera Wang gown, took a ride on Lake Como on a wooden speedboat. They wanted a quiet moment together on their wedding day.
The Club For the after-party, their friend, a D.J. named Gallivanter, transformed the wedding venue into a club by bringing house music and bagpipes. “I was like, ‘Make this a D.J. set,’” Franklyn said. “‘I want people to feel like they are in the club.’”
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