Route 66 and the Girl I Almost Didn't Meet

I was supposed to be on Route 66 with my girlfriend. We'd planned it for months—two weeks, Chicago to Los Angeles, staying in motels, eating at diners, seeing all the weird roadside attractions. Then, three days before we left, she broke up with me. Said she needed to 'find herself' or something. Classic.

So I did what any reasonable person would do: I went anyway. Alone. In a 1998 Honda Civic that had seen better days. My friends thought I was crazy. My parents thought I was having a breakdown. But I'd already taken the time off work, already booked the motels, already planned the whole thing. I wasn't going to let a breakup ruin my road trip.

The first few days were rough. I drove through Illinois, Missouri, Oklahoma, and I was miserable. Every diner reminded me of her. Every motel room felt too big. Every roadside attraction felt pointless without someone to share it with.

Then I hit Texas. Specifically, a diner in Amarillo called The Big Texan. It's famous for their 72-ounce steak challenge—eat it in an hour, it's free. I wasn't going to try it (I'm not insane), but I went in for lunch anyway.

That's where I met Emma. She was my waitress, and she had this energy that just filled the room. She asked me about my trip, and I told her the whole story—the breakup, the solo road trip, the existential crisis I was having in a Texas diner. She listened, really listened, and then she said something that changed everything.

'You know what? Screw her. You're on Route 66. You're doing something most people only dream about. Don't let someone else's decision ruin your adventure.'

We talked for two hours. She was working a double shift, but she kept coming back to my table, refilling my coffee, asking me questions. She told me about growing up in Amarillo, about her dreams of traveling, about how she was saving up to go to Europe. I told her about my job, my life in Chicago, my plans for the trip.

When I left, she gave me her number. 'Text me when you get to California,' she said. 'I want to know you made it.'

I did text her. Every day. I'd send her photos of the places I was seeing—the Cadillac Ranch, the Painted Desert, the Grand Canyon. She'd text back with encouragement, questions, and stories about her day. By the time I hit California, I realized I was falling for her.

I turned around. Not all the way—I made it to LA, saw the Pacific, took the photo I'd been planning to take. But then I drove back. Not the same route, but close enough. I wanted to see her again. I wanted to tell her how I felt.

When I walked back into that diner two weeks later, she was there. Same shift, same section. She looked up, saw me, and her face lit up. 'You came back,' she said.

'I had to,' I told her. 'I realized something on the road. The best adventures aren't about the places you go—they're about the people you meet along the way.'

We're getting married next year. We're planning our own Route 66 trip, but this time we're doing it together. And Emma? She's coming to Europe with me. We're going to see all the places she's been dreaming about.

Sometimes the best trips are the ones that don't go according to plan. Sometimes the person you're supposed to meet isn't the person you started with. Sometimes you have to drive 2,400 miles to realize that the best part of the journey isn't the destination—it's who you find along the way.