A Love of Sea Monsters Was the First Clue

Two friends and a sea monster brought Caitlin Kiernan and Kenny Kaplan together. These were not your average friends, nor sea monster. The creature came courtesy of a 1970s children’s television show about two boys and their briny buddy. The friends were a bit more timely.

The couple’s story begins in 2014, two years after Ms. Kiernan, 50, was diagnosed with breast cancer. Five surgeries and six months of chemotherapy later, her nine-year relationship had broken up and she was robbed.

“I can’t begin to tell you what a terrible time this was,” said Ms. Kiernan, a writer living in New York. “Yes, breast cancer is a health crisis, but it has also caused a major identity crisis for me. After losing my breasts, half of my hair, my smooth skin and my relationship, I no longer recognized myself or my life. It was devastating to the soul. “

While she wasn’t interested in dating, she knew she should at least get the training wheels off. So when her good friend, Juliette Levy, suggested going out with her brother-in-law’s best friend, a recently divorced music manager named Kenny Kaplan, she agreed.

“Caitlin is a unique person,” said Ms. Levy, a New York publicist. “She is a unicorn and has a great mind and energy. It was more, here’s someone I love so much, and Dave had an incredible relationship with Kenny. I didn’t know Kenny that well, but we ventured into loving these two people and said, what’s the worst that could happen? “

The brother-in-law in question, David Masor, had known Mr. Kaplan for years and felt that Mr. Kaplan and Mrs. Kiernan would at least spend a pleasant evening together. “Kenny is a very thoughtful person, very introspective,” said Mr. Masor, 47, who is one of the founders of the Home Applause real estate company in Montclair, NJ. “He has a spiritual side to him and he would do anything for a friend or family member.”

“He’s always supportive and there in a non-judgmental way,” he continued. “He may seem aloof at first, but it doesn’t take him long to remove that layer to discover that he is fun and confident and can talk about any topic.”

Their first date was at a wine bar on Manhattan’s Upper East Side. As they browsed through topics, they discovered a shared appreciation for ‘Sigmund and the Sea Monsters’.

“I connected with that show because I always felt like a fool in my family during my childhood,” she said. “So when Kenny knew about something from my childhood, it was a huge sign.”

Not only did 46-year-old Mr. Kaplan know the show, he also had the toy characters in his office. “I liked the aesthetics,” he said. “I liked everything.”

He liked everything about her too. She was very put together and stylish, while often looking like he just came out of a mosh pit from the 1990s. “I’m pretty relaxed so I liked that she had the assertiveness people have from here, but when we got deeper and started talking, she had a playful side, she’s very open,” he said.

Mr. Kaplan is also Jewish, and although Ms. Kiernan grew up in an Irish Catholic household in Middletown and Stone Ridge, NY, she was associated with Judaism and had seriously considered converting long before she met him. He also had two children, Carly, now 14, and Jonah, 11, which appealed to her, given that childbirth was one of the victims of her cancer. Chemotherapy put her into an early menopause.

After the night, he took her to her car, gave her a quick kiss on the cheek, and asked for a second date. She said yes.

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“She was electric,” he said. “She just lit the room.”

But there was a hitch, as so often.

During this time she was still finishing her cancer treatments. Between Mrs. Kiernan’s and Mr. Kaplan’s first and second dates, she had traveled to Virginia for the final stage of her treatment: nipple tattoos. She wrote an article about the tattoo parlor, recorded by a film crew, which was published on The Times’s Well blog. The story went viral and she panicked.

“I was so connected to women going through reconstruction and often their husbands and partners were not supportive,” she said. They look down on a reconstructed chest. It had never been discussed before. I was like, ‘He doesn’t want to date me anymore.’ It can be very embarrassing; you show your breasts to the world. “

Mr. Kaplan had seen the story and the video. But he was the opposite of ashamed. Instead, he told her how strong and brave she was. “She does important things for other people, and I am all for that,” he said. She took her experience with her and gave people hope, as opposed to ‘woe me’. I liked the fight. “

They went on a series of active dates: a painting and wine class; a sushi and sake-making class; and a private stand-up paddle boarding lesson on the Jersey Shore. They got closer and closer. Mr. Kaplan encouraged her to use her experience as a survivor and beauty producer at Amazon to write a book to help other cancer patients. That book, “Pretty Sick: The Beauty Guide for Women With Cancer,” was published in 2017.

He suggested taking a trip to Boulder, Colorado that same year for an early morning hike to see the sunrise.

“We are both independent and respect each other’s needs,” he said. “We are both looking for adventure and love to travel, but she is the first to push me to do what I want. If it’s something I’m interested in and she isn’t, she won’t suggest an alternative. She will say, ‘Go do it! You should!’ and the same goes for her. “

They planned a March 2020 wedding in Napa, California, but Covid-19 squashed that idea. They awaited the pandemic in Freehold, NJ, Mr. Kaplan’s hometown, with his mother and two children.

They finally married on March 20, 2021 at the Mark Hotel in Manhattan to a small group that included Mrs. Levy, Mr. Masor and their husbands. Rabbi Judith B. Edelstein, with whom Ms. Kiernan had studied for five years before her conversion last year, conducted the ceremony.

“The thing about our relationship is that neither of us intended it to be a relationship,” said Ms Kiernan. “We just wanted to have fun and laugh. But what we got out was so much more. We fell in love not only with each other, but also with life. “

When March 20, 2021

True The Mark Hotel, New York City

Star Lensman Mark Weiss, a celebrated photographer whose subjects included the Rolling Stones, Kiss and Madonna, captured the couple’s wedding day. He and Mr. Kaplan are friends and he offered his services.

The wedding attire Mrs. Kiernan designed her dress with Madeline Gardner of Morilee. “With all the wedding dresses out there, I couldn’t find one that flatted my body,” said the bride. “I was very aware of what my reconstructed breasts and chemopause-induced curves looked like.” After an eight-month search, Juliette Levy, the friend who introduced her to Mr. Kaplan, put her in touch with Mrs. Gardener. The groom wore a cobalt blue Ravazzolo suit.

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