When I Was 25: Leaving Town

About 6 months ago, I installed the Timehop app on my phone. After awhile, I started to notice that my posts from early 2010 and prior were the most cringeworthy. There was a noted change in what and how I posted in 2010 compared to years that followed. I posted a lot of mundane things- doing laundry, being tired, traffic, short lines at Trader Joe’s. I know people post about that stuff all the time, but I generally think that posting lame stuff on social media that only you find interesting denotes a lack of self-awareness.  Your baby waved at a cat out the window of the car today? So what? The man on the bus next to me this morning did the same thing. Anyway, the marked change in my mid-20s was more choice than natural progression. My 25th year was the year I finally did something. Like, besides getting baked and writing bad sketch comedy. I have a “say I’m gonna do it, but then don’t” problem; I come from a long line of procrastinators. But that year, after talking about how much I wanted to see the world, I enrolled in a TEFL training program in Costa Rica that would begin in late May.

The beginning of my 25th year found me in my apartment, filled with someone else’s shit. After Christmas, my then best friend had dropped out of law school and run off to start a new life in Mexico. In her wake, she left me with a bunch of her shit. Like, pretty much her entire apartment. My studio apartment was filled with boxes, appliances, and books. I had to clear a path from my bed to the bathroom. It was a metaphor for the previous five years- she unloaded on me and I let her. Michelle and I had an intense, hilarious, and outrageous friendship that took place under a cloud of skunky smoke, peppered with unnecessary, bitter fighting. Its story is a book in itself. Michelle was a funny, brilliant person. But there was more there. She had a bad dad, a history of volatile behavior, and an extended family that enabled dysfunction. The ensuing pain that caused, combined with my then need to save, control, and play the martyr was a toxic combination. Our lives had twisted into a codependent coil and my life didn’t feel like it was mine. Although it would still be years til we finally stopped speaking, we were finally apart and I looked forward to focusing on me alone and living independently. I dropped her crap at her mom’s and adjusted my focus appropriately.

In February, I applied for the Costa Rica program. Two weeks later, I was accepted. Til May, I decided, I would prepare, enjoy my time left at home, and take a Spanish class. I did not, however, anticipate the Tall Dark and Handsome Musician.

At my 25th birthday party, I was feeling saucy and drunk and had decided I wanted to end the night with one of two guys there. There was my sometimes crush, Brandon, from my sketch comedy group, and then there was the Tall Dark and Handsome Musician (TDHM), a friend of a friend who I’d met a few months earlier. Neither of them ended up back at my place that night, though. Instead, I ended the night with my gay best friend, Nate, as usual. But TDHM had picked up on my vibes, and a few weeks later, we hung out. We went out for Mexican and stayed up til 4 am, drinking wine, passing a bowl, and talking. It was intense and I was into it. Our second date lasted 24 hours and involved me ditching work to take a day trip to Indiana with him. I know, nothing says romance like “Indiana”, but in truth, it was the most exciting thing I’d done in too long. Before TDHM, my love life had been stale. It hadn’t worked out with the sweet but schlubby doctor the year before and my online dating endeavors fell flat. There was Tom Nevin in college, who I had and on and off long distance thing with for a spell. He had once told me he wanted to name his son “Champion” and hold him in the ruins of a church, so y’know, maybe not the man of my dreams. I sobbed about him about three times and eventually moved on. My naive 25-year-old self had begun to wonder if I was broken. It seemed that relationships were popping up all around me and I was bemused by every guy I met. When TDHM came along, though, it felt natural, like it was supposed to feel all along, but hadn’t. TDHM was smart, very funny, kind, had great taste in music and a southern accent. What more do you want?

Besides the fact that TDHM was so much fun, I was going to leave in May and that gave me the tenacity I hadn’t been able to muster up with other guys. I think he felt similarly; he’d gone through some heavy stuff the year before, but this situation was safe and there would be no long-term commitment.

TDHM and I had a few months together and it was spring in Chicago. Summer is sexy and fall is snuggly, but I think there’s something about a spring romance that is especially exciting. We are crawling out from the depths of an arduous winter and spring in Chicago can be magic. There’s excitement and promise in the air- we made it, winter is over, “Yes, we would like a spot on the patio.”

I didn’t mind dragging myself into work on 2 hours of sleep, I was leaving anyway and the fatigue was worth it. I remember looking at the empty wine bottles on my kitchen table with pride; they were trophies for sexy, fun times with a hot, cool guy. On one of my last days in town, we rented bikes at the beach on a whim. We rode along the coast of Lake Michigan swerving back and forth and ringing the bells. We went around to the back of Museum Campus and shared a J on the water. Once good and buzzed, we marched (literally) up the stairs to the aquarium, where we spent the afternoon giggling at marine life. Telling it now, it seems like a scene from a Kate Hudson rom-com. It was so good, it was cheesy.

The word “bittersweet” hung in my mind. Yes, this was great, but I had enough foresight (thankfully) to see that leaving was necessary. My curiosity for new places and experiences had been gnawing away at me for years. In five short years, I would be 30 and people would be telling me to hurry up and settle down. Now was the time to go.

I was supposed to leave his place at 8 am on my last day in town, but I didn’t make it back to my irritated parents until that afternoon. Neither of us wanted me to leave and neither of us wanted to say it. I kissed him goodbye, he said something funny, I left. I pulled away and turned up the radio and Fergie’s “Big Girls Don’t Cry” was playing. I started to cry, full well knowing how stupid it is to cry while listening to Fergie.

Early the next morning, I hopped on the plane.


What is that feeling when you’re driving away from people and they recede on the plain till you see their specks dispersing? It’s the too-huge world vaulting us, and it’s good-bye. But we lean forward to the next crazy venture beneath the skies.

– Jack Kerouac, On the Road


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