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Conor Thomas Cahill was wearing a Santa suit and a cast boot when he made eye contact with Jenna Ann Wynne at the Public House in Midtown Manhattan in December 2015.
A group of mutual friends had met at the bar for drinks during SantaCon, a yearly Santa Clause convention in Manhattan. Ms. Wynne, a wedding singer, had to work that night, but she stopped by the bar before heading to her gig.
The two started chatting, and Mr. Cahill explained that he had broken his foot while playing basketball a few weeks earlier. They exchanged numbers, and for their first date, they met at Kinha Sushi, a restaurant in Garden City, N.Y.
Ms. Wynne, 31, sings at about 50 weddings a year and is usually busy working on the weekends. She said that dating had been difficult for her at times because people were often dismayed by her busy schedule. But Mr. Cahill, 32, was impressed by her career.
Ms. Wynne started singing at weddings in 2012. At the time, she was a 19-year-old student at Pace University and a trained singer looking for a viable career option. At a cousin’s big New York City wedding, which included a 12-piece band, she looked at her mother and said, “Oh my God, this is what I want to do.”
The following week, she auditioned for Hank Lane Music, a New York company that oversees 20 bands. She was placed into the Bobby Attiko Band, for which she was a lead singer for two years. Then, she started her own band: the Jenna Wynne band.
Ms. Wynne and Mr. Cahill, both from Nassau County on Long Island, were texting nonstop and started hanging out with their mutual friends. “It was not hard to start falling in love with Jenna,” Mr. Cahill said.
Three weeks later, after their first date, he asked her to be his girlfriend. In November 2016, they got a dog, a Siberian husky named Maya. In May 2017, she moved into his place in Long Beach, N.Y.
Ms. Wynne graduated from Pace with a bachelor’s degree in communications. Mr. Cahill also received a bachelor’s degree in communications from the Catholic University of America. He is a senior account executive at SMP Nutra, a manufacturer of vitamin supplements in Brentwood, N.Y.
The couple connected through music. Together, they watched “American Idol” and “The Voice” and danced at many concerts in New York. He introduced her to the electronic dance music world, and she introduced him to artists like Celine Dion, whose songs she frequently performs at weddings.
“I live, eat, sleep, breathe weddings,” Ms. Wynne said.
[Click here to binge read this week’s featured couples.]
On Feb. 3, Ms. Wynne celebrated her own wedding, after Mr. Cahill proposed on the boardwalk in Long Beach, in February 2023.
They wed at the Liberty Warehouse in Brooklyn in front of 230 guests. Sheila Cahill, Mr. Cahill’s sister who received a one-day New York State officiant license, officiated.
The couple enlisted the Bobby Attiko Band for their wedding. “He taught me everything I know,” Ms. Wynne said. “It is such a full circle moment.”
Ms. Wynne walked down the aisle to “My Heart Will Go On” by Celine Dion. For their first dance, the couple executed the moves they had practiced together in their living room, including a spin into a dip and a lift. They danced to “I Was Made for Loving You” by Tori Kelly and Ed Sheeran. “Everyone was cheering,” Ms. Wynne said.
After their first dance, they had their father-daughter and mother-son dances. Then, Mr. Cahill brought Ms. Wynne’s grandmother onto the dance floor. As the couple danced with her on the dance floor, Ms. Wynne started walking toward the stage, confusing everyone, including Mr. Cahill.
Before the wedding, guests had kept asking Ms. Wynne if she would sing at her own wedding. (“Everyone was so annoying,” she said.) And each time, her answer had been the same: she always sang at weddings and wanted to simply enjoy her own. So when she stepped onto the stage and started singing “The Prayer” by Andrea Bocelli and Celine Dion, she took everyone by surprise.
“There wasn’t a dry eye in the audience,” Ms. Wynne said. “Everyone was hysterical.”
“Everyone caught our fever — we were just so head over heels in love,” Ms. Wynne added. “It’s been eight years. We’ve been waiting for this moment.”
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