May-December Matchup: 5 Couples compete in a Bill Belichick-inspired contest

Our May-December Matchup brought five couples into the studio to vie for a grand prize from Steven Singer Jewelers.

For months now, Fred Toucher has been obsessed with former New England Patriots Head Coach Bill Belichick having a 24-year-old paramour. If you've listened to the show, you're well aware of this. You've probably seen the fisherman-and-mermaid photo, too.

For Valentine's Day, the show was tasked with cooking up a contest for one of our favorite clients, Steven Singer. We let Fred's obsession light the way, and what we came up with made for a pretty entertaining hour or so of radio.

A week before Valentine's Day, five couples joined Toucher & Hardy in studio, all with significant age differences between the two partners. We took some time to get to know them, find out how they met, and quiz them on each other.

Thanks to Mike and Brooke, Betsy and Chris, Dave and Becca, Fred and Rachel, and Steve and Audra for taking part in the May-December Matchup. And thanks, of course, to Steven Singer. Check out the video below to see who won!

Want more? Follow Toucher & Hardy on Instagram for highlights and more clips from the show.

Here we are with the Boston Calling 2025 update. Yes, we'll dig into the lineup. But there's a lot going on at this year's version of the fest to discuss.

Boston Calling Music Festival has been going strong since 2013. Back in those days, it all went down on City Hall Plaza in Boston. And it happened twice a year: one weekend in May, and another weekend in September.

In 2017, Boston Calling moved to its current home at the Harvard Athletic Complex in Allston. The previous year, it became a once-a-year thing, happening on Memorial Day Weekend. I've been to all but one Boston Calling. Here's a history lesson.

The Festival team took a ton of fan feedback into account when planning this year's iteration. Gone are the Red and Green stages. There will now be one main stage with a turntable, providing seamless entertainment without having to slog through the crowd.

The improved layout should help concertgoers get around, too. You'll also see more water stations and have access to indoor space on the grounds to get out of the sun and cool down when needed. You can learn more about the 2025 improvements here.

Hit the Boston Calling website for all the details on tickets, including on-sale dates, packages, and more. If you're looking to win a pair, make sure you're listening to the Toucher & Hardy show all this week, then again as the festival gets closer.

If you want the skinny on who to see this year, keep scrolling. I've highlighted a handful of acts scattered across the three-day festival that I think will be worthy of your eyes and ears. After all, I'm the guy who's there ever year. Trust me.

Boston Calling has done outstanding work in recent years to feature Boston's wide-ranging music scene. Future Teens are a local indie rock standout and worth checking out on Friday.

Obviously, right? For real, though, I caught the Robinson Bros. doing a solo acoustic gig in Boston right before the COVID pandemic. They're rejuvenated and their new album, Happiness Bastards, has some great music on it.

The duo has collabed with everyone from Roger Waters to The War on Drugs. They're Boston Calling alums and they're always good for a tight set.

The Boston band blends a batch of rock genres into something that's uniquely theirs. Another standout act from the local music scene that's getting their well-deserved Boston Calling moment.

When you have an opportunity to see one of the greatest, most influential rap acts of all-time, you take advantage of that opportunity.

When Mr. Morello takes the stage, you can bank on a bevy of songs from Rage Against The Machine, Audioslave, The Nightwatchman, and whatever covers he's fancying at the moment.