Most people hate icebreakers. That said, they’re often a necessary inconvenience, so you may as well sweeten the deal with food. My favorite/least hated one for the classroom involves giving everyone a handful of Starbursts, then requiring them tell something about themselves based on the color. Red is a hobby, yellow is a random fact, orange is a goal for the class, orange is your bucket list. Or something like that.

I always include the bucket list category because it’s so telling about my students, to find out what they want to do in life. And they love learning about me.

Last time I did it, I used my orange Starburst to tell them I want to both pick up a hitchhiker and be a hitchhiker. And when I say this, the kids universally freak out. “You can’t do that! That’s not safe! That’s really f’ing stupid!” Yeah, whatever.

A year-and-a-half ago, I found myself wandering around Door County, Wisconsin. I took the ferry as a passenger, no car, to Washington Island, which really confused the ticket lady. “You realize it’s a three-mile walk to town, right?” Yeah. No problem. I didn’t tell her this, but I figured if I got tired of walking, maybe someone would give me a ride back to the docks.

Washington Island stavekirke

Sure enough, after I’d checked out an awesome little church in the woods and was heading back, an old guy in a pickup stopped and offered me a ride. It’s not quite what I had in mind when telling my kids I wanted to hitchhike, but concerned friends assure me that yes, it was hitchhiking. One thing down.

Since then, I’ve been trying to find someone to pick up, but it never works out: either my kid is with me, or they have too much stuff/dog for me car, or I’m going the wrong direction.

Last week, I was at the gas station airing up my bike tires when I noticed a scruffy kid and dog, surrounded by scruffy gear, sitting in the shade. I asked him if he needed a ride, and where he was headed.

“South.”

“How far south?”

“As far as you can take me.”

“I can take you to the next town. Let me ride home and get my car. I’ll be back in about twenty minutes.”

I was absolutely thrilled by this. I wrote a story about an inexperienced hobo, “Riding the Rails,” which was published by Hobo Camp Review in 2012, but I’d never really had a chance to talk to anyone about their experiences. This would be my chance for some great research.

“Cricket,” as he preferred to be called, was very quiet at first, barely answering my questions. He’d been traveling for about nine years (I’m guessing he was about twenty-five), had been to forty-eight states, and was making his way south to train to become a truck driver.

As the miles passed, he opened up more. He explained how to hop a train, why people in Massachusetts are crazy and Indianapolis is not a nice place, and the best ways to deal with asshole police officers on power trips. He didn’t finish high school, he said, and had been traveling since, staying with friends and working odd jobs, but he was getting tired of it and wanted something more permanent. I told him a little about the students I worked with, the at-risk kids everyone gave up on, and how sometimes they just needed someone to put things in a perspective they could understand. Sometimes, they just needed someone willing to give them a chance.

And then I got to see his sense of humor.

I asked him who gave him more rides, men or women. He told me I was the first women to give him a ride in nearly two years, and I mentioned people thought it was a bad idea because he might be a serial killer.

“If I was a serial killer,” he responded, “don’t you think I’d have my own car? Or five or six of them?”

As we neared our destination, nearly seventy-five miles from where I’d picked him up, we discussed the best place to drop him off. Downtown was out, because it was mostly just college kids walking or biking.

I asked him if he’d considered getting a bike.

“Well, actually,” he said, “I’m gonna get five more dogs and hitch them to a sled, to pull me around. I do too much walking.”

I was really kind of disappointed to drop him off. I’d had a great conversation with him and learned a lot. For his part, he told me it was the best ride he’d had “in a long minute” (he told me that most rides he got were about two-five miles, just from one tiny town to the next, usually in the back of a pickup with no one talking to him). If it hadn’t been for his dog frequently licking my face, and me needing to pick my kid up, I would’ve kept driving him.

I make a point of talking to people who are different from me. Everyone has a story, everyone can teach you something, if you’re just willing to give them a chance.

I know I am; are you?