IT HAPPENED TO ME: My Ad On Craigslist Rideshare Led Me To Love

If I wanted to find true friends, find humanity, maybe this was the way to do it—go on a cross-country road trip with a stranger!
Publish date:
June 15, 2015
Dating, love, craigslist, hippies, craigslist encounters, Sex,, Rideshare

The other day I asked three random people, “What is the first word that comes to mind when you hear "Craigslist"? They responded:

  1. Murder
  2. Apartments
  3. Creeps

The first thing I happen to think about when I hear Craigslist:

  1. My boyfriend Jose.

It’s January 2013. I'm living in downtown Chicago wearing the most obnoxious paisley leggings ever stitched into existence. I have a pocket of ylang ylang resin to crush throughout the day to cleanse my energy. I write daily journals on the status of each chakra and have a sudden affinity for palm readings, hula-hooping, and mass quantities of the Red Hot Chili Peppers after seeing them the previous summer at Bonnaroo.

It’s also my sophomore year of college as a Midwestern transplant in a city where I know no one. I'm 12 hours away from my hometown, my friends, and now that I am finally in college, I spend most evenings alone watching Breaking Bad on Netflix.

I am desperate to justify my loneliness, and this is how I do it — I am lonely because of how the planets align. I figure people will be attracted to my spirit if I am soaking—almost drowning—in "calming energy" and "good vibes."

One night on my daily Netflix search I came across the documentary Craigslist Joe. The film followed a man who goes searching for humanity in America via Craigslist—as in, he finds all food, water, shelter, and transportation for free online. His journey leads him across and out of the country. Families open their homes and show him the landscape of their lives. While recapping his experience at his Welcome Home party, he starts tearing up because he can’t believe this all happened to him.

When I finished the documentary, my heart was fluttering like a caged bird whacking against the bars. Maybe this was the thing that could snap me out of my funk! If I wanted to find true friends, find humanity, maybe this was the way to do it—go on a cross-country road trip with a stranger!

I began searching Craigslist’s Rideshare forum. I crafted a bulletin talking about the film, my intentions behind traveling, and my background. A few people responded quickly, mostly truckers who wrote short responses in ALL CAPS that left me less than enthused.

One person, however, sent one of the most important, coherent messages of my life.

His name was Jose. He wrote a paragraph about how he had seen Craigslist Joe and loved the film too. He wrote that he went to Bonnaroo with five strangers from Craigslist the same summer I went, and saw Red Hot Chili Peppers to boot. He was interested in doing another road-trip, and would I like to chat over coffee or lunch?

We made a date to meet.

My roommates at my dorm all thought I was crazy for doing this, but my heart thumped and adrenaline flew from my fingertips. I felt invigorated. When Jose picked me up in his car, he was wearing a beanie. His hands were sweaty, and his eyes were huge, lovely and brown.

Instead of coffee or lunch like he suggested, I insisted that we go to a free meditation session at a hip yoga studio in Lincoln Park. Jose and I cracked the ice as we drove and held elbows as we skidded on black ice to the studio.

In a circle of five people all desperate for free meditation, the instructor whacked a gong to symbolize the beginning of the silent session. Three minutes later, I heard a skittish sound. I peeked through one closed eye—Jose was still sitting up, adjusting his boots and trying to get comfortable, flicking his eyes open and looking around.

He laid his gaze on me and smiled before shifting again. I choked down a giggle as the other hyper-fit yogis began to scowl with eyes closed in his direction.

In the following weeks, we did things like sit in parking lots drinking wine watching the snow fall or listen to the Red Hot Chili Peppers and play footsie on my bed.

We were never once bored with each other.

I had never felt that before.

Soon enough it looked like what we had in the somewhat-platonic way we had it needed to burst.

Here is the thing: No matter the chemistry we had, I was hell-bent on hiding the fact that I didn’t feel comfortable in who I truly was. And if I wasn’t comfortable with myself, I couldn’t be with him no matter how much I wanted to be.

When May thawed, Jose texted me one night saying he wanted to take me to dinner and I told him to meet me at a Starbucks miles from my apartment. Over my massive cup of coffee and his shy eyes, I told Jose that he had issues in his first chakra that he needed to address—without any mention of my own concrete problems I was too righteous to admit to.

As he drove me home I bombarded him with questions. I scoffed, “Why do you even like me?”

He slowed to a halt for a STOP light and stared. “I’ve never met anybody like you. Isn’t that enough?”

We had a falling out after that night. I spent the summer wondering what happened to him, but I didn’t have the courage to give what we had a real shot.

One October night I finally sent him a nonchalant text in a veiled attempt to catch up. When I pressed SEND my stomach fluttered like that locked bird in a cage again.

I had given the paisley leggings away and I felt more like me—the true me—than I had in a long time.

He texted me back.

We made a date.

Something magical happened when we saw each other again—we just clicked. And for the first time, I didn’t need to question any of it.

Since Jose and I started dating, we’ve finally taken our road-trip. Multiple, actually. We’ve joined flash mobs in the streets of New Orleans, skidded across frozen lakes in Wisconsin, and intertwined pinkies wandering down the streets of my hometown in Annapolis, Maryland.

We keep finding adventures in the landscape of each other.

One night after one of my classmates mentioned finding miscellaneous "work" on Craigslist, I went searching on the Craigslist Personals thinking the friend meant prostitution. I began clicking and scrolling through all of these ads of men seeking men or women seeking men and I thought, wow, people actually do this? People actually post pictures of their penises online and get a response?

Jose came over after work that night. He leaned back on my bed with my laptop and opened Craigslist to begin searching for a new apartment. His eyebrows furrowed. “Karen, what’s this?”

The previously blue links to Craigslist forums were turned purple below all of the categories I’d clicked in the Personals. Jose opened each purple forum and suddenly all of my curiosities were outlined in color, pictures and ads and all.

I tried to explain, and when that didn’t work I combatted, “Ew, I would never go searching on the Personals for a serious ad on Craigslist.”

Jose’s eyebrows softened and he pointed to the screen. “Karen, we met on Craigslist. From this.”

I looked down at my fingertips. His paranoia made sense but my argument back didn’t. We had met on Craigslist.

Whenever I have told people how Jose and I met, they respond, “Oh, wow, that’s great you met off Rideshare and not the Personals.”

But why? Who is to judge how people find each other?

Jose and I wouldn't have met if I wasn’t lonely and busy being a pretentious hippie. We don’t live in the same city and we don’t have similar hobbies.

But this is the thing—we were made up of chances. He happened to see Craigslist Joe and become inspired by it at the precise time that I was.

I guess, in some ways, the planets do align.

Even though I am somewhat disgusted with the version of myself that led to my Rideshare post, being in my hippie-dippie phase gave me faith to take a chance. And this was a beautiful chance.

I think the reason Craigslist Joe cried at the end of his journey wasn’t solely because of the beauty of his experience. I think he might have teared up because he was overcome with all of the slight turns on the roads that led to the places it did, to the people he met along the way.

Maybe in that moment, all of the chances he took piled up and glowed like wintertime black ice and snow.

I know the feeling.