The similarities connecting Kelsey Ann Castañon and Kelsey Hughes Whitaker were undeniable. They had the same first name, were both born in July 1990, raised in Kansas, came out in their 20s and, unbeknown to each other, moved to New York around the same time.
And where the coincidences ended, fate stepped in.
The two met briefly in Manhattan, Kan., at a party in 2011, thanks to another random connection — Ms. Castañon’s then-boyfriend and Ms. Whitaker’s ex-boyfriend were roommates. They met again in 2013 at a party in a clothing store in New York, but it would be 2018 before they made their first real connection.
Ms. Whitaker was “feeling inspired to make new connections with other gay, like-minded women in my community,” she said. “I heard through friends that Kelsey was dating women and hoped to meet up.”
She reached out to Ms. Castañon on Instagram.
In November 2018, the two met at Attaboy, a speakeasy on Manhattan’s Lower East Side, near where Ms. Whitaker was living. Unable to get in, they went across the street to a wine bar for a drink. They then stopped at the Flower Shop bar and restaurant for a game of pool, followed by the Grey Lady for a comedy show. By the time Attaboy could accommodate them, “it felt like we had been on multiple dates and that we had known each other forever,” Ms. Whitaker said.
High on conversation and connectivity, not to mention a few drinks, Ms. Castañon kissed Ms. Whitaker. “I wasn’t looking for a relationship,” she said, but “we kept uncovering all these layers of depth.” The kiss, she added, “felt like coming home.”
Their numerous similarities, however, gave them pause.
“We thought we were doomed because of them,” Ms. Castañon said, “and tried being friends for months.”
Ms. Whitaker agreed the similarities were a lot, but didn’t feel doomed. “We had grown in different directions only to come back to the same direction,” she said.
Once they gave in, they became inseparable.
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Sharing a passion for food, wine and travel, 2019 was spent falling in love as they visited California, Japan and Thailand.
Just one month before the pandemic Ms. Whitaker moved into Ms. Castañon’s Upper East Side apartment, which Ms. Castañon shared with two roommates.
Ms. Castañon, 34, is a senior director at PS, a digital lifestyle publishing company under Vox Media. She received a bachelor’s degree in journalism from Kansas State University. Ms. Whitaker, also 34, is the head of innovation and creative experiences at Mindshare, a global marketing agency based in New York. She received a bachelor’s degree in journalism from the University of Kansas.
In August 2020, the couple moved into a one-bedroom apartment in Clinton Hill, Brooklyn. A year later, they adopted Ziggy, a rescue mutt who brought their commitment to “co-parenting status,” Ms. Whitaker said.
While traveling in the Philippines in July 2023 as part of their yearly two-week birthday travel ritual — this one affected by Typhoon Doksuri — Ms. Whitaker proposed.
Ms. Castañon immediately said yes, and six months later counter-proposed at Attaboy, with the lead guitarist of Incubus, Mike Einziger, and his wife, the master violinist Ann Marie Einziger, serenading the couple in front of friends and family. (The couple both grew up as fans of Incubus, and the Einzigers have since become friends.)
The couple were married Nov. 1 at the Brooklyn municipal courthouse by their best friend, Alana Peden, who was ordained for the occasion by the Universal Life Church. On Nov. 9, the couple celebrated their marriage with 70 friends and family in Sayulita, Mexico.
Despite their similarities, their differences became their most important qualities.
“She’s a beautiful wordsmith; I express things visually,” Ms. Whitaker said. “When that’s combined it’s a powerful and beautiful balance.”
Ms. Castañon also spoke positively about their distinctions.
“We are inherently different in the best ways, which makes us work,” Ms. Castañon said. “I didn’t want to marry myself or someone who had the same thought process and reactions.”
She added, “Kelsey helps me see the world in a difference lens and adds dimension and intrigue to my life.
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