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 Kansasfortune coin slot machine, 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.”
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