Nadya Tolokonnikova of Pussy Riot Marries John Caldwell

When Nadya Tolokonnikova, one of the founding members of the anti-establishment punk collective Pussy Riot, reached out to John Caldwell on Discord, an encrypted messaging app, he asked if she was a bot.

“She just said ‘haha,’” said Mr. Caldwell, who was already familiar with her work. “I was very suspicious.”

Ms. Tolokonnikova had developed an interest in cryptocurrency and blockchain and had heard about Mr. Caldwell, a partner at a financial services company who specialized in crypto, from a friend. “I was jumping on Zooms with random people with no romantic intentions, just learning about crypto,” she said.

They met for dinner a few days later, in mid-September 2021. “It ended horribly,” Mr. Caldwell said. “She faked a call to Europe and left.”

Ms. Tolokonnikova, an activist, musician and artist, described herself as a “super introverted person,” and said she normally spaces out meetings with new people. But at the time, she was in the process of crash educating herself on a new topic, and had therefore scheduled several meetings in one day, and the dinner with Mr. Caldwell was last.

“I was overwhelmed,” she said. So she left abruptly. But, she said, “it was not a reflection on John at all.” In fact, she had been intrigued by their conversation about reproductive rights and religion, and by Mr. Caldwell’s suggestion that she tap into the deep pockets of the crypto world to raise funds for causes she was interested in.