Sept. 6, 2019, in Philadelphia
The Saturday of Memorial Day weekend 2017, Jim, his Shore housemates, and what seemed like all of Avalon crammed into the Whitebrier Restaurant. His pals wound up next to a group of women on a bachelorette-party mission, and he found one of them mesmerizing.
“She was vibrant and beautiful,” Jim said. He introduced himself.
Kaila was doing her best for her soon-to-be-married friend, but inside, she was grieving. Her grandmother, Marie, had lost her husband, Richard, just days before, and she and her grandmother were devastated. “I was not in the partying mood,” Kaila said. “My mom convinced me to go, just for the one night, and said she’d pick me up early the next morning.”
Kaila had to admit this Jim guy was a nice, handsome distraction. “We bonded over having the same breed of dog growing up – a West Highland White Terrier,” said Kaila, now 29. In addition to swapping tales of Jim’s late, great Taffy and Kaila’s Gracie, they discussed their close-knit human families and discovered a shared Italian heritage: Jim, now 39, is 100% South Philly Italian. Kaila, who grew up in Havertown, is half Italian, half Irish. After 30 minutes of enjoyable banter, he asked Kaila to dinner in Philadelphia the following week, and she invited him to a wedding three weeks hence.
“It was hard seltzer’s fault,” Kaila said.
As promised, Kaila’s mother, Geralyn, arrived at 7 a.m. “I just had the best night ever,” Kaila told her.
Jim felt the same. He lived in Manayunk, and his first text suggested dinner at a place right across the street. Kaila, who lived at home in Haverford, gently declined. She also turned down a place in Havertown, but agreed to Fat Salmon in Old City – a neutral location.
On their second date a week later, Jim had a question: “You invited me to that wedding the night we met. Are you sure you want me to go, because I’ll give you an out if you don’t.”
“You should definitely come,” said Kaila, a public relations specialist at Children’s Hospital of Philadelphia.
“OK, great. I got a new suit for it,” said Jim, who is assistant vice president of IT sourcing and vendor management at Radian Group.
Date two was in progress when they discussed date three. “I thought I would take you to Parc for your birthday,” Kaila said. There, she gave him a tie to go with his suit.
“She was not only willing to take me out for my birthday on our third date, she gave me a present!” Jim said. “It made a big impression that she was invested, and so was I.”
“I was telling all my friends and family, ‘He’s just so nice. I can’t believe how kind he is!’ But I was waiting for the other shoe to drop,” Kaila said. “Over time, I realized that truly is just who he is, for real. And at the end of the day, what you really want is someone to be nice to you, to treat you with respect.”
Wedding weekend came, and Jim picked Kaila up in Haverford – where he met her mother, her father, Frank, her grandmother, her sister, Jules, Gracie, the West Highland Terrier, and Ellie, the Maltese.
Jim loved meeting everyone, and thought he had made a good first impression. Kaila thought so, too, but said they wouldn’t know for sure about her father unless he offered Jim a bottle of homemade wine. Jim brought Kaila home after the wedding, then got back in his car to drive home. Her father came running out with a bottle of wine.
The couple was soon in love. “I had been 100% my true self since day one. That I could be my true self, that he loved and accepted that, was wonderful,” Kaila said.
Jim fell for Kaila’s kind heart, and the way she made it clear he was firmly ensconced in it. “I just wanted to be with her, and I knew she wanted to be with me, which is just as important,” he said.
These days, Jim and his father, also named Jim, help Frank with the wine-making.
The couple had known for almost a year that they were headed toward marriage. In July 2018, they had a long weekend in Nashville planned, and Kaila was certain a proposal was coming then. The weekend prior, Jim asked her to join a former colleague and his wife for dinner. Jim and Kaila started solo with drinks at Moshulu and then headed to the now-closed Cooperage for dinner, where Jim said his friends would be waiting.
Kaila hadn’t realized until they pulled up that the restaurant was at the Curtis Center – which had been her dream wedding venue until her must-have wedding caterer, Cescaphe, stopped catering there.
“Let’s just walk through it, just to see it,” Jim said. Kaila was lamenting as they walked up to the fountain and Jim said, “We won’t actually have our wedding here, but I have to ask you first.”
That last bit caught Kaila’s ear.
“Is this a joke?” she asked more than once.
Jim knelt and pulled out a ring. “Will you marry me?”
She said yes, and they had a celebratory dinner, not with Jim’s friends at the Cooperage, but with her parents and sister and his parents, Suzanne and Jim, at La Fontana.
The ceremony was held at Saint Monica Church – Jim’s parish – and included a full Mass. The couple laid flowers at the feet of the Virgin Mary and then brought flowers to their mothers and Kaila’s grandmother.
Kaila’s lament over the Curtis Center ended when she found the Lucy – a newish Cescaphe venue the couple booked based on an artist’s rendering. Not only did Jim change into a white dinner jacket to make his new bride happy, he managed not to spill anything on it, a minor miracle.
The flowers, including orchids and hydrangea, were pink – a nod to the bridesmaids’ hot pink dresses – and lime green. The name of the Old Fashioned-inspired signature cocktail was announced via a sign featuring a watercolor of dog Ellie. The sign is proudly displayed at the couple’s Wynnewood home.
Their 225 guests jammed to Jellyroll, who mastered “Magic Carpet Ride,” the song of Jim’s Saint Joseph’s fraternity, Lambda Chi Alpha. “The song plays and we all jump up and down, and at the end, everyone carried me while I was crowd surfing,” he said.
After the ceremony, as she and Jim began their walk back up the aisle, Kaila squeezed his arm and whispered, “We have to slow down because we are only doing this walk once.” They were married, she thought, and everyone they love had gathered from everywhere to support them.
Jim was in total agreement. “I thought, ‘Let’s slow burn this thing. Let’s not think to 10 minutes ahead. Let’s enjoy every second,’ and that’s exactly what we did.”
The couple splurged on wax-sealed invitations featuring a custom watercolor of the Philadelphia skyline on the inner envelope.
Two weeks in Italy, including a stay at the Hotel Santa Caterina, where the pool is carved into a mountain and overlooks the Mediterranean Sea, a visit to Pompeii, a morning boat ride around Capri, and a cooking class featuring ravioli and chocolate torte.
Officiant: Father Joseph Kelley, Philadelphia.
Ceremony: Saint Monica Roman Catholic Church, Philadelphia.
Reception and Catering: The Lucy, Cescaphe Event Group, Philadelphia.
Music: Jellyroll, Chadds Ford, Pa.
Photography: Rachel Pearlman Photography, Gladwyne, Pa.
Flowers: Frannie’s Fancies, Philadelphia.
Kaila’s attire: Dress: Martin Thornburg for Mon Cheri.
Shoes: Christian Louboutin, a gift from the groom.
Hair and makeup: C.E. Facial Artistry, Philadelphia.
Jim’s attire: Rudi’s Formal Wear, Philadelphia.
Planner: Cescaphe Event Group.
Transportation: First Class Rolls Royce, Willingboro, N.J.
Invitations: Chick Invitations, Philadelphia.