Jacqueline Ann Agostinelli and James Ernest Squires ignored their mutual attraction, remaining friends for more than five months after they met. Eventually, they both said, it became “impossible to resist.”
The two were introduced in October 2020 through an acquaintance who thought Mr. Squires, the owner of an information technology company, could help Ms. Agostinelli revamp her life-coaching website.
At the time, she was coming out of a long-term relationship of more than 25 years and moving from the West Palm Beach, Fla., home she had shared with her partner into her own apartment in that city. Mr. Squires lived about 20 minutes away in Jupiter, Fla., with his mother, Beverly May. She had dementia, and he had moved from Freeport, N.Y., in 2014 to be her caretaker.
He, too, was fresh out of a relationship that had lasted more than two decades, and neither had love on their minds.
“I was not in any way looking for a committed relationship,” Mr. Squires said.
Ms. Agostinelli added, “I definitely didn’t want to jump into anything right away.”
They spoke by phone about her website, and when they later met in person at Mr. Squires’s mother’s home, their spark was instant.
“Jacqui was beautiful, and my interest was piqued in wanting to know more about who she was,” he said.
Ms. Agostinelli was intrigued as well. “James possessed a hippie vibe and was soft and kind and quiet,” she said.
They worked on her website and then fell into a long conversation about politics before realizing that they both pursued music on the side. Ms. Agostinelli, who holds a bachelor’s degree in musical theater, performed in musicals at theaters across South Florida. Mr. Squires, a former full-time musician in Miami, is a member of Hot Sauce Moon, an acoustic rock, folk and New Orleans blues band that performs throughout South Florida.
Their second meeting, a week later and also at Ms. May’s home, stretched for hours and ended with dinner at her dining table. “My mom was there, and even with her dementia, it was obvious that she really took to Jacqui,” Mr. Squires said. “It was just so easy, all of us sitting there and talking.”
By their third meeting, in December, Ms. Agostinelli said that she knew she wanted more than friendship. “I remember thinking to myself, ‘Oh boy, I’m in trouble,’ because I was having some incredible feelings for him,” she said. She was 57 then and, after a divorce and long-term relationship that didn’t work out, had begun to doubt whether she would ever find lasting love.
“Jacqui came out of nowhere,” Mr. Squires said. “I was 69 and never thought I would find ‘the one,’ but being with her was like fireworks.”
Mr. Squires, now 74, grew up in Battle Creek, Mich., and South Miami, Fla. He is the founder and owner of Tele Computers Services, an information technology company based in Jupiter. He is also a singer and drummer for Hot Sauce Moon, an acoustic rock, folk and New Orleans blues band and a member of Sweet Basil, a duo he founded with Ms. Agostinelli in January 2025.
Ms. Agostinelli, 63, is from Rochester, N.Y. She runs a life-coaching company, Your Curvy Coach, which aims to empower women 50 and older to achieve their dream lives. She is also a member of Hot Sauce Moon. She holds a bachelor’s degree in musical theater from the Boston Conservatory of Music, now known as the Boston Conservatory at Berklee.
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The pair’s relationship took a romantic turn in March 2021 when, following a meeting at Ms. May’s home about YourCurvyCoach.com, Mr. Squires asked her to accompany him to the live music venue Double Roads Tavern in Jupiter, where his friends were playing guitar and singing.
As he sipped a martini and she drank wine, they held hands and sang along. The night continued at Das Beer Garden, where they listened to Americana music and had a lively conversation about their love for eclectic music, their childhoods and their careers.
“It was the first time we had gotten personal, and the more I found out, the more drawn to her I was,” Mr. Squires said.
Ms. Agostinelli said she couldn’t stop looking at him. “He was just so different from anyone else I had met.”
Six hours later, close to midnight, Mr. Squires walked her to her car, where they shared their first kiss.
“It literally swept me off my feet and made me tingle from head to toe,” she said. “It was that passionate and intense.”
After that night, they began seeing each other regularly, texting throughout the day, with Mr. Squires often suggesting ideas for dates. They often frequented local bars and live music venues. “We had a routine of starting off the night at my mother’s house, where the three of us would have dinner, and then going out,” he said. “We would end up back at her house in the hot tub in the backyard, talking until late.”
Within a few weeks, they were together every day and night. “I had lived a life of performing in musical theater shows, and James introduced me to bands, which were completely new to me,” Ms. Agostinelli said. “I relished every second and never wanted to be anywhere else but with him.”
Mr. Squires wasn’t the only one who welcomed Ms. Agostinelli’s presence. “My mom adored Jacqui, and we were like a happy family,” Mr. Squires said. “She had issues, including episodes of yelling because of her dementia, and Jacqui was loving and helpful through it all.”
When Ms. May died in July 2021 at age 93, Ms. Agostinelli officially moved in. The couple continues to live in the home today.
Living together felt “natural,” they said, but it also meant some adjustment. Ms. Agostinelli described herself as “open and a straight shooter,” while Mr. Squires is more reserved. “I would have to pull things out of him, which was frustrating,” she said. “ I have learned to respect our different communication styles.”
Their opposite sleep schedules were also a contrast. Mr. Squires, a night owl, stays up until 2 a.m. and sleeps until 10 a.m. Ms. Agostinelli, an early bird, prefers to be in bed by 9 p.m. to watch her favorite TV shows. She rarely sleeps past 7 a.m., but has taken to slipping back into bed for a few hours so they can wake up together.
And then there was the question of marriage. “James made it clear it wasn’t for him, but I told him early on that I was wife material, not girlfriend material,” Ms. Agostinelli said.
“I didn’t believe that you had to get married as an expression of love,” Mr. Squires said.
Despite their differences, they continued to grow closer and found ways to stay connected. Ms. Agostinelli was drawn to performing so much that she joined Hot Sauce Moon in January 2022 as a singer. Three years later, the couple formed Sweet Basil, performing songs from the 1950s to today across a range of genres, accompanied by recorded backing tracks.
By then, Ms. Agostinelli had come to terms with being Mr. Squires’s “forever” but not his wife. “I loved him and decided it was worth it to be with him no matter what,” she said.
When he proposed on Oct. 9, 2025, over dinner at Takato, a Japanese restaurant in Fort Lauderdale, Fla. — five years to the day after they met — she was “floored,” she said. “He asked our server to take a video of us, then pulled out a velvet pouch with his great-grandmother’s two wedding rings,” Ms. Agostinelli said. “I almost fell out of my chair.”
“Getting married just seemed like the next evolution of our relationship and something that I had a change of heart about,” Mr. Squires said.
They wed on April 9 before 30 guests at Memorial Park in Stuart, Fla. The Honorable Carolyn Timmann, clerk of the circuit court and comptroller in Martin County, officiated. The couple hosted their reception on the patio of Lynora’s, an Italian restaurant in Palm Beach Gardens that they both love. The menu featured their two favorite dishes: margherita pizza and beef and pork meatballs.
The night ended with the newlyweds alone in their backyard hot tub until 2 a.m., gazing at the moon and sipping white wine.
On This Day
When April 9
Where Memorial Park in Stuart, Fla.
Dressed to Impress DaisyMae, Ms. Agostinelli’s Jack Russell terrier, wore a lavender dress printed with daisies, along with a matching harness, leash and a pearl-adorned taffeta bow. The outfit was a gift from her dog nanny, Ann Sergent.
Old Is New Again Ms. Agostinelli chose a diamond wedding band with a vintage feel to complement her existing set from Stampar Jewelers in Jupiter, Fla., where the rings were also refurbished. Mr. Squires, who had never worn rings before, designed a custom band for himself with a diamond and a brushed gold finish.
Seeing Each Other First The couple opted to forgo tradition and got ready together at a friend’s home nearby to avoid wrinkling their outfits — his, a navy blue Armani jacket paired with a baby blue T-shirt and white jeans, and hers, a white calf-length dress with a fitted bodice and flared skirt she found on Amazon.
A Line of Roses The table settings were meant to be simple, without flowers, but a close friend, Tracy Sands, surprised the couple with store-bought roses in varying colors. They were laid horizontally across the tables at Lynora’s with greenery beneath, forming an unbroken line symbolizing a long, well-lived life together.
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