Chapter 2: The Bet

When I first started dating Caleb, his friends made bets—actual money on whether we’d last more than a month. It was like some twisted game to them, all played out over bottomless coffee at Lou’s Diner. Lou’s always smelled like burnt toast and old coffee, the kind of place where the waitress calls you “hon” and the booths are patched with duct tape. Everyone in Maple Heights knew Caleb’s family. The Harts run this town. Getting mixed up with them? It’s never simple.

But my roommate told me, “This Caleb Hart is a little different. I heard he’s easy to win over, never loses his temper with girls, and always parts on good terms with every girlfriend.”

She wasn’t wrong.

But between us, it never felt like anyone was chasing anyone. It just… happened.

I was in my second year of grad school, drowning in research. I needed an out-of-print English monograph—something nobody seemed to have. I posted on Facebook a dozen times, and just when I was about to give up, I got a reply.

The message was half sarcastic, half sincere—

[My dad might have it. If you want it, hit me up. I’ll do a good deed.]

I replied instantly.

After that, to thank him, we met up twice more. We clicked. The last time, he stood under a streetlamp, eyebrows raised, looking almost too handsome for Maple Heights. “Will we meet again?”

The glow made him look like he belonged in an indie movie. It made me wonder: in a year or two, after all this fades, will we still run into each other?

The night air was cold. I could’ve said no, but instead, I grinned and shot back, “I heard you’re easy to win over. Is that true?”

He burst out laughing. “Then try.”

Sometimes you meet someone so different—unapologetic, calm, like they own the world—and you just want to be close. Truth is, I’d seen him before, a long time ago, on one of my worst days. I’d just gotten to town, my wallet stolen at the Greyhound station. The rain stung my cheeks, mixing with tears. My shoes squelched on the cracked sidewalk as headlights swept past. I was miserable, soaked, and on the verge of falling apart.

A pickup slowed beside me. Caleb leaned out, voice soft. “Hey, it’s okay. I promise I’m not some creep. Need a ride? Or just someone to talk to?”

Of course I didn’t get in. But he waited a moment, gentle, not pushy.

Later, I always wanted to thank him, but we never crossed paths again. In a place like Maple Heights, sometimes even meeting once feels like fate.

Not long after that, we got together.