Without hesitation, he says, “Yes. I will.” Then, in a voice peppered with innuendo, he adds, “I never leave a woman hanging.”

My brain whirs with questions I could volley at him in our next episode. Like, what do you really think when you walk into a date? Or what are you hoping for when you swipe? Or maybe do you ever think about that night we spent together years ago? The night you definitely didn’t leave me hanging?

But I probably won’t ask that one. Because I certainly don’t think about that night with my brother’s best friend. I’ve moved on. I’ll just ask one of the other questions. No big deal.

“I’m in,” I say, accepting the challenge. Not only do I want to win, but I do want this date to work, dammit.

“And what do I get if I’m right?”

“You won’t be,” I answer.

“But what if he is?” Sadie puts in, the college-age producer herding two unruly cats.

“Fair question,” I concede, then turn my gaze back to Monroe, ready to make my own offer. “Fine, then you can ask me anything.”

I make it sound like a generous offer when, truthfully, I’m an open book. If Monroe takes this bet, he’s a fool.

But that gleam in his eyes turns a little mischievous, and he reaches a hand across the table. “Let’s do it.”

After we shake, Sadie handles the phones, taking a few calls from listeners. “And we’ve got Eleanor Longswallow on line one,” Sadie announces. “She says she has a very important question for the Heartbreakers and Matchmakers.”

I brighten as Sadie gives us the signal that our self-proclaimed superfan is on air. “Hey, cuties,” she says in a familiar, gravelly voice that feels like your grandma’s hug.

“Hi, bestie!” I say. “Please tell me you’re working on your tan.”

“And drinking mai tais,” Monroe adds.

“Only piña coladas for this old dame. Which brings me to my question—what should I pack for my…wait for it…honeymoon?”

I squeal. “He popped the question?” I’m giddy with excitement. We helped coach her through her burgeoning romance with the younger tennis instructor at her club. Guess it’s burgeoned.

“Please,” Eleanor chides. “I did. I don’t have time to waste waiting around for anyone. I asked my honey, and he said yes, and now we’re cruising around the world.”

“Congratulations!” I clap my hands together. “And as for what you should take on your honeymoon, I believe they say ‘less is more.’”

“Exactly what I was thinking.” Eleanor cackles. “What about you, Monroe? Would you have bet on that first date of mine going the distance?”

“Absolutely. I had a feeling way back when that you’d be glad you went for it with him,” Monroe says with a warm smile that’s different from the smirks he slings my way. But that’s fine. I don’t expect him to needle listeners like he needles me. “Now, be sure to have a good time. And that’s the doctor’s orders.”

“I will,” Eleanor says. “And you two should be sure to enjoy yourselves.”

She must mean on the show, so I add, “We always do.”

We take a few more calls from listeners who mostly say encouraging things about my ExtraDate prospect, and then it’s a wrap. Once we’re no longer recording, I push back from the table and gather my things. Sadie tells Monroe she has some listener emails to review with him. That’s his area, whereas I focus more on social media marketing, which means I’m free to go.

“I don’t have any clients till four, so I’ve got some time,” Monroe tells Sadie.

“Great.” Then she turns to me. “Good luck tonight. I’m rooting for you. But I hope he doesn’t talk about wine because that sounds snooze-inducing.”

Time to play my ace. “Elijah and I will have no wine talk! It’s going to be so fun. We’re going to Zelda and Nico’s Cheese Experience. It’s reserved seating and ours is at eight, so yeah. The date is totally going to last more than an hour.”

No one leaves the cheese experience early. It’s legendary. Maybe I played dirty, holding this Gouda and cheddar intel back. But I don’t care. Let Monroe eat his words when my date goes ExtraDate. Combo date. Extend-a-date.

But the cocky man just scoffs. “Doesn’t matter. It’s not going anywhere. You only do first dates these days.”

I fume, my brow pinching. “It’s not my fault! I keep getting bad matches.”

Monroe holds my gaze for a good, long beat, his bedroom eyes taking me in, roaming up and down until I wonder if Sadie should even be in the room. “Or maybe you don’t pick the right guys,” he says.