Can love beat the odds? Prediction markets are taking bets this Valentine’s Day that celebrity relationships can thrive — or break apart. By wagering money, bettors are setting the odds on the amorous relationships of high-profile figures, from Zendaya to Katy Perry.

For example, on Polymarket, an online prediction market, registered users can take a financial position on whether or not American pop star Katy Perry and former Canadian Prime Minister Justin Trudeau, who announced their relationship in December 2025, will be engaged by the end of 2026. As of early February, the probability of the pair committing to wed by then was 27%. To date, more than $22,800 has been wagered on the couple’s fate. 

Polymarket users are also betting hundreds of thousands of dollars on aspects of pop-star Taylor Swift and Kansas City Chiefs tight end Travis Kelce’s engagement, including whether or not they’ll be married before June 30, or if the bride will become pregnant before she weds (unlikely, according to bettors).

A similar bet is hosted on a prediction market called Kalshi, where the site puts the probability of Swift and Kelce marrying before Jan. 1, 2027, at 70%, based on customers’ bets. 

“In the spirit of Valentine’s Day, who doesn’t want to see two people find each other?” Melinda Roth, a professor at the Washington and Lee University School of Law, who researches prediction markets, told CBS News.

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The Free Press: Tough Love: Do I Like Being Single Too Much to Fall in Love?

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While she doesn’t personally wager money on prediction markets and has no skin in the game, she does have a preferred outcome.

“I’d rather bet on a love contract than a breakup contract,” she said.

Wisdom of the crowd

Polymarket, which operates globally and was forced in 2022 to shut down in the U.S., has since relaunched domestically under regulation by the Commodity Futures Trading Commission, or CFTC. Kalshi is similarly regulated by the CFTC in the U.S. and also operates globally. 

Experts in prediction markets say that U.S.-based users often access offshore markets on Polymarket, bypassing regulations using virtual private networks, without which Polymarket’s global sites would be off limits.

“Americans still bet on Polymarket’s non-USA platforms, but they have to go through a VPN, or call a friend or a cousin or whatever,” Prof. Roth said. 

Other amorous event contracts include: 

• Will Kylie Cosmetics founder Kylie Jenner and Oscar nominee Timothée Chalamet become engaged this year? Kalshi’s answer: 53% chance
• Will Zendaya and Tom Holland get married by December 31? Polymarket’s answer: 49% chance 
• Will Bill Belichick and Jordon Hudson be married before 2027? Kalshi’s answer: 27% chance

An expired market even let the public bet on whether or not Caroline Ellison, the former girlfriend of disgraced crypto entrepreneur Sam Bankman-Fried, would have a new boyfriend by the end of 2025. 

Such sites rely on the “wisdom of the crowd” theory, which holds that a large, diverse group of people has superior judgment to that of a single individual. Users’ bets determine a market’s odds, which shift in real time and indicate the likelihood of each outcome.  

In an interview with CBS News’ “60 Minutes” late last year, Polymarket founder and CEO Shayne Coplan characterized the platform as “the most accurate thing we have as mankind right now, until someone else creates some sort of a super crystal ball.”

Roth said there is at least some truth to Coplan’s assertion. 

“One way prediction markets work really well is because people do have knowledge, and they put their money where their mouth is,” she said. 

Odds of effective regulation are low

Critics of prediction markets say they allow insider trading, the illegal practice of trading a company’s stock based on nonpublic material, to fester, putting regular speculators at a significant disadvantage. 

“People are using inside information to profit at the expense of people on the other side who don’t have that information,” said Ben Schiffrin, director of securities policy for Better Markets, a nonpartisan advocacy group focused on financial reform.

Kalshi prohibits anyone with material non-public information on a contract from betting on it.

As far as playing the odds on romance goes, even those who warn about the sites’ potential pitfalls encourage consumers to be optimistic about love, as long as they are aware of the betting stakes. 

Rajiv Seth, a professor of economics at Barnard College, characterized betting on love as a relatively “harmless” pastime, “as long as people are aware that they may be trading against insiders, or people with better info than them.”

Roth also distinguished between trading on inside information and what she characterized as “superior knowledge.”

“Someone who knows that Justin Trudeau bought a ring would have a leg up on other bettors,” she told CBS News. “They are not using any skill or creating superior knowledge for themselves. They are taking material, nonpublic information and capitalizing on it.”

By contrast, a loyal Swift fan who has read everything under the sun written about and by the artist, “might be able to put two and two together,” to make an informed guess about her wedding date, she said. 

Coplan, Polymarket’s founder, doesn’t take issue with the allegation and says it’s actually a feature of the platform, rather than a liability, saying, “it’s sort of an inevitability that this will happen, and there’s a lot of benefits from it.”

Skeptics also say such markets increase access to, and encourage, gambling.

“They allow betting on pretty much anything, including celebrity relationships, and that opens up a whole other avenue to get consumers into gambling,” Schiffrin said.

Michael Selig, chairman of the CFTC, addressed prediction market regulation in recent comments, saying that while he wants the markets to flourish, he is directing the agency to draft rules governing so-called event contracts. 

“For too long, the CFTC’s existing framework has proven difficult to apply and has failed our market participants. That is something I intend to fix by establishing clear standards for event contracts that provide certainty to market participants,” he said in prepared remarks at a joint CFTC and Securities and Exchange Commission event on Jan. 29. 

Particularly when it comes to a matter as fickle as love, prediction markets face another challenge: connecting outcomes back to reality. That’s why they make the rules clear. For example, speculation about Chalamet and Jenner’s status would not suffice as evidence of an engagement. An official representative, or the couple, would have to make a public announcement stating their intention to marry.

“We’re engaged,” or “I said yes,” announcements would suffice for bettors who wagered money on the couple living happily ever after to cash in, according to Kalshi. But unconfirmed rumors would not.

Edited by

Cara Tabachnick

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New Yorker Shardil Ahmad always imagined meeting his future girlfriend at a coffee shop: he’d spot her thumbing through a book, curiously approach and they’d fall into easy conversation.

“I very much describe myself as a romantic guy— I’m big into ‘meet-cutes’ and stuff like that,” said Ahmad, 28, recalling a time he met a woman on the subway.

So when his mom suggested a matchmaker,  the first-year medical resident was skeptical.

“I wanted to be the one to discover this person,” he said.

But after a few months, Ahmad, with little time to spare outside the hospital after working six-day weeks, decided to sign up.  

He joins a growing number of Gen Z singles seeking alternatives to algorithms amid reports of widespread dating app fatigue and declining user numbers. For some young people looking to foster connection in real life (IRL), matchmakers make sense.

“I’m just letting someone take the wheel,” Ahmad said. 

After the swipe surge, interest in dating apps drops 

During the COVID-19 pandemic, dating apps saw record highs; Tinder recorded 3 billion swipes in a single day.  Match Group, the parent company of dating apps like Tinder and Hinge, reported a surge in subscribers from the previous year.

Six years later, some disenchanted daters are logging off. Match Group recently reported a 5% decline in paying subscribers from the same period last year, as Gen Z embraces in-person opportunities they missed out on during the pandemic.

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The Free Press: Tough Love: Do I Like Being Single Too Much to Fall in Love?

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Maria Avgitidis, the founder of matchmaking agency Agape Match and a fourth-generation matchmaker, says she’s seen a rise in outreach from young singles. Matchmakers from across the country told CBS News they’re seeing an uptick in younger clients craving in-person connection and moving away from dating apps.

“Many of them graduated high school or college via Zoom, so they really do want that intentionality of in real-life experiences,” Avgitidis said.

Even though Gen Z is delaying marriage and parenthood, the majority eventually want those things, according to the latest available data from the Pew Research Center. Nearly 70% of adults ages 18 to 34, who have never been married, say they want to get married one day, with men and women equally likely to say they’d like to get married.

“If you’re not dating for marriage, what are you dating for?” Ahmad said.

Over the last decade or so, Avgitidis said she’s seen people burned out by online dating and seeking things a profile alone can’t reveal. 

“The language dramatically shifted about why someone was using us,” she said, noting that things like values and politics don’t always come across in a dating app profile. She noted that Gen Zers especially tend to consider things like lifestyle, hobbies and having a life plan.

“They really appreciate and value authenticity,” she said. “It’s not so much about fitting into a certain aesthetic.”

Matchmaking is trending— but love isn’t cheap

A rising interest in matchmaking has been reflected in popular culture, from reality shows such as “Indian Matchmaking,” which has since expanded into “Jewish Matchmaking” and “Muslim Matchmaker,” to movies such as “Materialists” starring actress Dakota Johnson as a jaded Manhattan matchmaker, Lucy.

Matchmaking services can cost anywhere from a few thousand to a hundred thousand dollars, depending on what’s included. Some high-end matchmaking firms charge $15,000 to $25,000 for curated matches. Avgitidis said that at Agape, services can range from $30,000 to $100,000. 

Working with a matchmaker is a multi-step process, usually involving an in-depth initial survey, a screening interview, and a consultation before a match is made, experts said. Matchmakers create detailed profiles of their clients and prospective matches, including information about their dealbreakers and preferences and religious and political ideologies. 

For Ahmad, the financial aspect contributed to his initial hesitation about seeking out matchmaking services.

“How am I gonna spend this much on love?” he said. 

But vetted matches and intentional dates ultimately felt like a time saver for Ahmad, who said he recognizes that the services may be inaccessible for some people his age.

“I would recommend anyone to do this if they had the time and financial capabilities to do so,” he said. 

Members of Gen Z seeking the matchmaking experience, but feeling daunted by the price, still have options within the matchmaking world. Some matchmaking agencies have free databases, where you can submit a profile to be considered as a potential match for a paying client. Agencies also offer packages which can include individual coaching sessions, dating app profile feedback and dating support communities.

When in doubt, Avgitidis reminds daters that good old-fashioned meddling from family and friends is always an option. After all, dating used to be a collective experience, Avgitidis said, with friends and family members involved.

“One day, we all just started swiping alone on the couch,” Avgitidis said. “We are not meant to date alone.”

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