When Nadya Tolokonnikova, one of 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.

Despite Mr. Caldwell’s sense that the meeting had been a disaster, Ms. Tolokonnikova reached out again, and the two decided to work together on a new venture: UnicornDAO, a fund-raising and investment vehicle focused on female, nonbinary and L.G.B.T.Q. artists and creators.

Nadezhda Tolokonnikova, 34, was born in Norilsk, Russia, and studied philosophy at Moscow State University. At 22, before she could complete her degree, she was imprisoned for nearly two years for her role in “Punk Prayer,” a public performance piece that protested the Russian government’s close relationship with the Russian Orthodox Church (the protest was also the subject of an HBO documentary in 2013). In 2014, she and another Pussy Riot member, Maria Alyokhina, founded an independent news outlet in Russia called Mediazona. Ms. Tolokonnikova was married previously to Pyotr Verzilov. They split up in 2016.

Ms. Tolokonnikova’s continued outspokenness against President Vladimir V. Putin and his government landed her on Russia’s list of “foreign agents,” a label the authorities use to suppress opposition figures, according to rights groups. Because of concerns for her safety, she does not disclose where she lives. In 2019, she received an honorary doctorate from the Rhode Island School of Design, fulfilling a personal dream. She is currently working on a memoir.

John Ferguson Caldwell, 40, was born in Providence, R.I., but grew up in Pacific Palisades, Calif. Mr. Caldwell graduated from Pepperdine University in 2006 with a bachelor’s degree in art. He worked in surfing tourism in the Marshall Islands, managing a private island and organizing luxury yacht charters, until the pandemic began. After returning to the United States in March 2020, his interest in cryptocurrency and blockchain led him to join Wave, a financial services company. He is a founder of RFLXT, a company that is building a platform of artificial intelligence and crypto tools for creators.

After Russia invaded Ukraine in February 2022, Mr. Caldwell and Ms. Tolokonnikova led an effort to raise $7.1 million in cryptocurrency for Ukraine. The crypto wallet they used for the fund-raiser publicly listed Mr. Caldwell’s name. “All my friends were like, ‘The Russian government will put you on a list,’” Mr. Caldwell said. “I don’t think it’s a coincidence that was the moment Nadya got little hearts in her eyes.”

“That was a very clear moment for me,” Ms. Tolokonnikova said. “I really cherish kindness and bravery and consistency and high moral values in people.”

Mr. Caldwell, too, was full of admiration for Ms. Tolokonnikova. After she messaged him on Discord, he decided to learn more about her and watched the speech she gave at her trial in Russia in 2012, in which Ms. Tolokonnikova described herself and her fellow Pussy Riot activists as “freer than the people sitting opposite us and representing the prosecution because we can say everything we like, and we do.”

“It’s one of the most inspiring moments in humanity’s recent history,” Mr. Caldwell said. “And that’s just in the background. She’s funny and beautiful and smart and goth — and now vegan.” Mr. Caldwell has been vegan for more than two decades and succeeded in converting Ms. Tolokonnikova to the diet in the fall of 2022.

Now they enjoy eating at new vegan restaurants together. “John knows every single place for vegan food on planet earth, and it’s always the best,” Ms. Tolokonnikova said.

They also like to stage political actions together; in November, for example, they protested against restrictions on abortion rights in front of Indiana’s Supreme Court building. “We brought a giant inflatable vagina, and I came up with the contraption to inflate it, so I was holding it,” Mr. Caldwell said.

“His friends called him the Man Behind the Pussy,” Ms. Tolokonnikova said.

Both struggle with depression and other mental health issues and find comfort in helping others. “Most people, if one of the members of their partnership was put on a criminal wanted list in their country and exiled and couldn’t visit their home and their family and everything they knew, they would consider it a challenge,” Mr. Caldwell said. “But it’s just our reality. We’re not sitting around feeling sorry for ourselves. We just want to be helpful.”

He added that he does not prioritize happiness. Instead, he said, “I prioritize ideals and being useful and creative and being supportive of people around me.”

Ms. Tolokonnikova said she found Mr. Caldwell’s approach comforting. “I don’t even necessarily know what happiness is,” she said. “I spend most of my time on my art or my activism. I don’t spend much of my time on human activities, like going to a bar or just having fun.”

And so, fun was the top priority for Mr. Caldwell’s proposal. “Nadya has been through a lot,” he said. “I wanted to give her something cute and nice and kind of traditional.”

A few days before a trip to London, Mr. Caldwell commissioned Alligator Jesus, a jewelry designer and friend, to create an engagement ring for Ms. Tolokonnikova. Within 24 hours, Alligator Jesus delivered a black gold ring with diamonds and a pink sapphire. Mr. Caldwell also asked Gera Riot, Ms. Tolokonnikova’s 15-year-old daughter, for permission to propose, which she granted.

On Nov. 11, Mr. Caldwell and Ms. Tolokonnikova were joined by Marina Abramovic, a close friend who, Ms. Tolokonnikova said, “spiritually adopted” the couple, in central London. They were there to see a short art film, “Nadya Means Hope,” in which Ms. Tolokonnikova burns a candle in the shape of an eggplant emoji, play on an enormous screen in Piccadilly Circus. At the end of the video, a poem written by Mr. Caldwell appeared on the screen, followed by the words “Will You Marry Me?” in Russian and English. Mr. Caldwell got on his knee and took out the ring.

“I fell on the ground because I was so surprised,” Ms. Tolokonnikova said. Literally. And then she said, “Da!”

They were legally married on Jan. 12 at a courthouse in Los Angeles. Afterward, Nathan Monk, a priest who left the Russian Orthodox Church because he did not support its stance on gay marriage, led a short ceremony in their friend’s yard in front of about 200 guests.

“He spoke about Ukraine, about the fact that this love was brought together by challenges of the modern world, but also our common wish to make the world a little bit better, more just,” Ms. Tolokonnikova said.

Ms. Tolokonnikova’s daughter made the party’s playlist, which featured Soviet pop and contemporary Russian trap. For food, Ms. Tolokonnikova suggested serving pickles and vodka, but Mr. Caldwell insisted on something more robust.

He asked Wendell Hooper, a friend who is a chef, to cater. “He answered my call a week before,” Mr. Caldwell said. “He said, ‘This is normally planned six months in advance,’ and I said, ‘Welcome to Pussy Riot.’”

They served vegan meatballs, vegan charcuterie, vegan shrimp and eggplant caviar. Ms. Tolokonnikova baked a large vegan Napoleon cake, dyed it black and assembled it in the shape of a cross, a symbol she uses often in her artwork.

The dress code was “gopnik,” a word that encapsulates a style of dress, music and art reflecting the working class in the former Soviet states in the 1980s and 1990s. Mr. Caldwell asked Mark Hunter, a.k.a. the Cobrasnake, to serve as wedding photographer. “I like his pop-event club style.”

Guests showed up in tracksuits, house slippers, Adidas slides and newsboy caps, and one brought an accordion. Ms. Tolokonnikova wore a corset top from Adidas, a skirt from Depop with a petticoat over it, a faux leather jacket and velvet, high-platform Doc Martens.

She sewed three stripes — the Adidas trademark — along the arms of a suit jacket for Mr. Caldwell, using a skill she picked up in prison. “I thought I would never sew again,” she said. But for this occasion, she was happy to.

“Everybody was saying it was the most comfortable party they’ve been to,” Ms. Tolokonnikova said. “It was absurd and goofy at times, and the overall vibe was very cozy.”

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On This Day

When Jan. 12, 2024

Where Los Angeles

Breaking Bread A friend gave Ms. Tolokonnikova and Mr. Caldwell a loaf of dense rye bread, which they pulled from opposite sides until it broke. Per Russian tradition, whoever ends up with a bigger chunk will be in charge. “We did it exactly equal,” Ms. Tolokonnikova said. “Well, maybe mine was a little bit bigger.”

Bitter Cries At Russian weddings, when guests shout the word “gorko,” or “bitter,” the newly married couple should immediately kiss. But not all the guests at Ms. Tolokonnikova and Mr. Caldwell’s international wedding understood what the word meant. “They would scream at me and he’d be at the opposite side of the house,” Ms. Tolokonnikova said.

Master of Ceremonies A friend of the couple’s who is a translator and speaks Russian and English, Max Lawton, acted as the “tamada,” or toastmaster, in the Georgian tradition. Besides organizing the toasts, Mr. Lawton led the guests in playing games, like one in which people hold a balloon in their lap and others try to sit on it until it pops.