Wanted: True Love. Reward: $100,000.

For most of Mati Roy's life, dating was far down on his priority list. Although he tried dating apps half-heartedly, and would have welcomed a relationship if it had developed naturally, pursuing love didn't seem worth it.

But as Mr. Roy entered his 30s, his priorities began to shift. He pondered for a long time about the ethics of having children and then decided he wanted one of his own.

In December 2021, Mr Roy put together an online dating biography, known as a 'date-me-doc', and encouraged people to share it online. He noted that he was 6 feet tall, did not drink, smoke or use drugs and was less interested in spending time together than typical couples.

Kids were important, so to sweeten the pot, he offered $2,000 to whoever introduced him to the person he would eventually legally co-parent with. (Mr. Roy chose this wording so as not to rule out adoption.) The money was an experiment, and the amount reflected an amount that might motivate people to participate.

Mr. Roy, now 33 and a project manager at OpenAI, called the reward a “dating bounty.” One friend offered another $1,000 with a simpler demand: It would go to whoever introduced Mr. Roy to someone who brought him “a lot of joy” for at least 18 months. Another friend, Anatoliy Zaslavskiy, who goes by Toli, added $500 with the same 18-month condition, bringing the full premium to $3,500.

Mr. Zaslavskiy, now 31 and an engineer at Dropbox, was so excited about the idea that he decided to offer his own dating bonus: $100,000, which would be paid out on a four-year vesting schedule.

“I really liked the funding structure of startups and I thought, 'If this works in the financial world, why can't it work in the dating world?'” said Mr. Zaslavskiy, who chose the amount after analyzing his spending and thinking about how much he wanted to invest in love.

After the first year of the relationship, the amateur matchmaker would receive a lump sum of $25,000. The person would then receive monthly payments of approximately $2,000 until the full amount was paid out or the couple separated.

For those with a greater tolerance for financial risk, Mr. Zaslavskiy proposed an alternative: a profit-sharing initiative. If the potential partner agreed to the terms, the matchmaker would receive 10 percent of the couple's combined income under a similar vesting schedule. If their income were to increase, the premium would also increase.

Mr. Zaslavskiy, like Mr. Roy, posted his bounty online. As the documents circulated, commentators derided the idea as not only unusual but also cringe-worthy.

Love and money

The term 'bounty' conjures up images of reward posters for catching criminals and is reminiscent of the 'bug bounties' that technology companies offer to people who discover flaws in their systems. But Mr. Roy and Mr. Zaslavskiy's dating bonuses could be seen as a return to old-fashioned matchmaking.

Instead of swiping, they want to encourage connections to help them find a match — and indeed, that was once the main way people met their partners, said Michael J. Rosenfelda sociologist from Stanford who has done just that investigated how couples meet and stay together.

Mr. Rosenfeld believes that a dating bonus is sensible since friends and family are unable to make introductions.

“This is an attempt to put all hands on deck, and that makes sense to me,” he said. Moreover, he added, people don't view being single as an emergency, but rather as a state of life, so if you want to get your people to work on it, you have to kind of nudge them with the feeling that this is actually something that is very important.”

For Mr. Zaslavskiy, the oddity of the idea is part of its appeal. He wasn't afraid of being ridiculed if it offered more opportunities to find love, and he hoped the reward would attract the kind of open-minded person he'd like to date.

At the time, Mr. Zaslavskiy, who lives in Brooklyn, earned about $200,000 a year, so the monthly premium payments of about $2,000 would have been about 12 percent of his salary.

“I've looked at all these things in my life that don't bring me much value,” Mr. Zaslavskiy said. “At that point, I might be spending $13,000 a month, but do I need all that stuff I'm buying? Absolutely not. If I could spend $2,000 of that on finding someone I love, it would be absolutely worth it.”

He points to Blind, an anonymous gossip app used by some tech workers. “It's basically a bunch of techies complaining about their lives, as one colleague put it,” he said. “Many people there earn well over half a million dollars a year and yet they struggle with relationships. I think people on Blind would happily pay more than 10 percent for a satisfying relationship.”

Matchmaker, Matchmaker

For most people, $100,000 would be an eye-watering amount of money. But larger amounts have been put on the table before. A billionaire ever offered Rachel Greenwald, a professional matchmaker and executive fellow at Harvard Business School, a $1 million dating bounty if she found him as his husband. She turned him down.

Ms Greenwald said it was not surprising that it was mostly men who offered dating bounties: “Women think it sounds desperate, and men think it sounds like a power grab,” she said.

It's not that “dating premiums” don't exist in matchmaking. “Marriage bonuses” and “success fees,” because when “success” is defined more broadly than walking down the aisle, are par for the course. Ms. Greenwald estimates that a third of matchmakers have some kind of success fee included in their contracts.

But don't confuse the success fee with the matchmaking itself, Ms. Greenwald said. While some professionals – real estate agents, for example – work on commission, the most common matchmaking business model is a monthly commission with a success fee. For top matchmakers, the commission can be $10,000 to $75,000 per month for three to six months, with a success fee of $50,000 to $1 million.

The success-fee-only model is not how the matchmaking business works, Ms. Greenwald said. It doesn't recognize that what you're paying for when you go to a matchmaker is not just “success,” but the person's time and network and psychological expertise to understand and guide you.

That's why a dating premium may seem rude, even though paying for a dating coach or for a premium subscription to Hinge is fine, said Michal Naisteter, a professional matchmaker in Philadelphia. One person wants to pay for expertise and help with self-improvement, the other wants to 'put a price on love'.

A bounty claimed

After Mr. Zaslavskiy paid out his reward, he received about five introductions, two of which turned into video calls, but none turned into dates. After a reunion and breakup with an ex, he's dating again, and the $100,000 bounty remains active. He is now polyamorous, so the bounty is paid to the person who introduces him to his primary long-term partner.

Mr. Roy received approximately 27 introductions, which resulted in five video calls and one in-person meeting. None ended in romance, but his girlfriend Carrie Radomski, who had previously tried to trap him, shared his reward on her Facebook page. It quickly attracted attacks — and the attention of Ms. Radomski's Facebook friend Carissa Cassiel.

The honesty and specificity of his profile (Mr. Roy wanted at least two children and was into cryonics) appealed to Ms. Cassiel, and the reward seemed smart. But the selling point was noting how he took the criticism. Commenters said the reward was weird, or that the profile had too much information or that he sounded autistic, Ms. Cassiel, 39, said.

“I saw in the comments how he responded to people,” she said. “He was very gracious and said, 'That's a good point' or 'I should change that' or 'I could add something like that' or 'That's not how I feel.' He just handled everything beautifully, and that felt very important to me.

Ms Cassiel decided to comment in defense of Mr Roy. She pointed out that as a single woman, she liked to have a lot of detailed background information when evaluating potential dates.

Mr. Roy was in Canada and Ms. Cassiel lived in Georgia, but the two began messaging and then spending time together at a mutual friend's virtual hangouts. To find out whether they would work as a couple, Mr. Roy went to stay with Ms. Cassiel for a few weeks and then spent time in Mexico with her and Thane, Ms. Cassiel's son from a previous relationship.

Eventually, Mr. Roy moved to Georgia permanently. The couple married last April and are raising Thane together. Because the relationship lasted more than 18 months, $1,500 of the bounty was paid to Ms. Radomski, who plans to donate it to a nonprofit organization. Mr. Roy has not yet legally adopted Thane, but if he does, or if the couple has a biological child or adopts another child, Ms. Radomski will also receive the original $2,000 bounty.

Mr. Roy and Ms. Cassiel are excited about the possibilities of dating incentives. He thinks it's a way for people connecting others to get paid for their work; it is a sign of respect. Ms. Cassiel believes that without this message, she and Mr. Roy might never have met.

“I think it's brilliant, and it really gets people involved and caring,” she said. “I think it really shows motivation, drive and commitment. It is very exemplary of his personality. When he decided he was ready, he put his money where his mouth was.”