This cornhole league inspired a bounty hunt for single men. It's now sold out.

Yahoo

08-03-2025

Determined to find enough men to sell out his cornhole league for singles, Tommy Flaim decided to take an extreme, and somewhat comical, measure. He put out a bounty for straight single guys.
The offer? Fifty dollars to any person who would refer their straight single friends to sign up for the New York City edition of the event, which drew over 100 participants this week.
It's a marketing strategy that Flaim has successfully used since he started the event in Chicago in November. His league, Silly Sports, has been such a success that it has sold out events in 20 cities.
'IRL' (in real life) dating events have surged in popularity since the Covid-19 pandemic as people grow increasingly tired of the revolving door of dating apps. A Forbes Health study last year found that 80% of millennials and 79% of Gen Z singles are burned out on apps.
The alternative has become a rise in speed-dating events or run clubs to meet people. But some organizers of these events have said they've struggled to attract enough single straight men for an even ratio.
'We've noticed the girls are going to show up regardless, like they're willing to try anything,' said Flaim, whose videos on TikTok about the league have garnered thousands of views. 'And the guys are the ones we have to be very sensitive and calculated about in regards to how you attract them, how you recruit them, how you make them feel comfortable.'
The idea for the league came when Flaim was working at a bar that was looking to use its cornhole equipment more during weekdays. Having already run a pickleball league where people were looking to meet, Flaim realized it could be an opportunity to cater to the many singles sick of dating apps and looking for real-life connections.
And while pickleball requires some skill and exertion, cornhole is one of those casual lawn games that's much more accessible to the athletically impaired. Singles are paired up on a team and rotate out to meet new people over the course of an hour in a league that lasts about five weeks.
In nearly every major city, no matter how many marketing tactics he's tried, Flaim said 'finding men is ubiquitously difficult.'
'I feel like girls, there's an effort discrepancy,' Flaim said. 'I think girls are willing to do something that's as ridiculous sounding as speed-dating cornhole. … It's corny, no pun intended. And the guys that signed up, it was because of the bounty.'
Flaim, a gay man who had no prior experience with the heterosexual dating scene, added that his heart goes out to women.
'It seems very, very rough out there,' he said.
During Tuesday's event, held at Lawn Club in New York City's financial district, friends Jeniea Howard, 31, and Lacey Smith, 35, decided to come together. Howard makes dating content on TikTok and was excited when she saw Flaim's videos about his dating league coming to New York.
The two women have been on the dating scene for a while and agreed that no matter how often they go out, they had difficulty meeting men who were serious about dating.
'There's a weird tension between men who want a relationship, but they don't want to come off as eager, or they don't want to be tied down too quickly,' Howard said. 'I feel like a lot of men, even on dating apps, they'll say they're still figuring out what they want. But what they want is a relationship, they're just afraid to say it.'
Smith doesn't blame men for being nervous or hesitant because she admitted to working on her own bad dating habits. Both of the women felt the cornhole league was low-pressure, even if they didn't end up meeting their match.
'If everyone can just want something, we can all change,' Smith said. 'This doesn't have to be permanent, but, you know, that's hope. Hope is a valuable currency.'
Dating coach Stevie Bowen has seen the rising trend of dating events and the challenge of finding men to participate. Some of her own male clients have been hesitant to take the risk, she said.
'When you're going to a dating event, you're like, 'Hey, I'm looking for someone,'' Bowen said. 'You know, 'I'm trying to find someone.' And for a man — and for anyone — that's really vulnerable to say.'
Bowen says the men she speaks to perceive a lot more pressure around dating events, whereas women see it as more of an opportunity to build community. Women take the risk thinking they could make new friends or have a fun time even if they don't find a relationship in the end, Bowen said.
Bowen encourages her clients to see the events as a tool to try new things and work out their social muscles.
'You know, practice makes almost perfect, is what I like to say,' Bowen said. 'And I think that's what comes with dating and meeting people in real life. ... You just have to go up and do it, and it's gonna get easier the more you do it. And I think that's what these dating events are helping daters do.'
Everardo Montoya, 31, learned about the cornhole league from his friend Katie, who saw Flaim's TikTok call for men and encouraged him to go. Sick of the dating apps and struggling to meet people organically, he said he decided to step out of his comfort zone.
A bit of an introvert when meeting new people, Montoya said he's hesitant to approach other people because he doesn't want to feel like he's bothering anyone. But he found Tuesday's event fun and low-pressure.
'It's definitely less intimidating, for sure, because you know that everyone here is trying to find their person, right?' Montoya said. 'So it's like, even if you get rejected, it's just like, it's fine.'
Joe Wilhelm, 31, was actually looking to join a sports league and happened to start getting ads for the cornhole league on Instagram. Dating can be pretty horrible, he said, but even as a more personable type of guy, he wasn't sure about a speed-dating league.
'Maybe girls are a little more emotionally open to events like this — for a guy, not so much,' Wilhelm said. 'I mean, even for myself, I could talk to a wall, very social, but I had one of my friends kick me in the ass to tell me to come here.'
He guessed that maybe men could be 'a little hardheaded' about stepping out of their comfort zone. But once there, Wilhelm said most of his interactions felt easy and organic.
'I feel like everyone here that I met knows how to socialize … but I feel like today's generation is far from it,' Wilhelm said. 'Everything's behind a screen, and that's how they communicate. So I like how we're bringing back the history of dating and meeting people organically.'
This article was originally published on NBCNews.com