On an overnight stopover in Los Angeles in September 2017, Alicia Cepeda Maule arranged a meeting with her childhood crush63jili, Isabelle Claire Davis, at the Black Cat, a bar in the Silver Lake neighborhood.

They had grown up as family friends a few blocks apart in the Kenwood community of Chicago, but hadn’t seen each other since their teens.

Ms. Davis expected a quick catch-up drink, but ended up talking to Ms. Maule for hours. Ms. Maule, for her part, confirmed that her interest from decades ago was still there.

“I remember leaving and feeling like she’s the coolest,” Ms. Maule said. “She’s got the best taste in music, she smells the best.”

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After a second date a few days later when Ms. Maule stopped over in Los Angeles on her way back to New York City, they began a relationship.

“We didn’t really intend to start dating,” Ms. Davis said. “We just never stopped talking.”

Ms. Maule, 35, is a digital engagement director at the Innocence Project, a nonprofit group that works to overturn wrongful convictions, and a founder and chief executive of Givepact, a crypto currency philanthropy platform. In 2012, she was a project manager on Barack Obama’s presidential campaign. She has a bachelor’s degree in Africana Studies from Brown.

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