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Stories >> Challenge-a-Day

There is a Pittsburgh punk tradition called "fun-a-day." For the entire month of January, fun-a-day project participants pick something and do it every day. Someone might do "postcard a day," where they write a postcard to someone every day. Someone else might do "tresspass a day," where they make it a point to tresspass somewhere every day. The more ambitious amongst us might compose an animation every day or paint a small piece of art every day. And at the end of the month, there's a party for everyone to present their fun-a-day.

Picking your fun-a-day can be tricky. Just like some jobs which might initially appear enjoyable, but that inevitably become insufferable due to their repetitive 9 to 5 demands, by the end of January you might find yourself doing "not-fun-a-day." People who used to love writing postcards become sick of trying to fit their thoughts into those four sentences, and people who used to love tresspassing just want to sit quitely at home for once. So my housemate Jamian and I decided to do something together and alternate days to reduce the relentlessness of it all.

At first we settled on "internet date a day." We'd alternate going out on a date that was setup through the internet every day. While certainly terrifying, it seemed like an interesting way to spend the month, so we began scouring craigslist, signing up for every online dating site we could find, and blackening the skies of the internet with messages and responses to ads in an attempt to schedule enough dates in advance. As uninitiated internet daters, we imagined that the dates would flow freely enough for us to easily fill the month, but it turned out that neither of us managed to line up a single date in the week before January began.

The whole process was a lot more work than we imagined, so on January 1st we decided to switch projects. Instead of "internet date a day," we would do "challenge a day." Every day, we'd alternate giving each-other a challenge. The deal was that the person receiving the challenge had to complete it by the end of the day, otherwise that person owed the other an Indian Buffet (which had, for some reason, become the common currency for all bets in our life).

Throughout the process, coming up with a challenge embodied a constant tension between wanting to do something really challenging and the knowledge that you yourself would be receiving a challenge from this person the very next day.

I started it off by challenging Jamian to go to Whole Foods and ask a stranger there out on a date. He ended up prowling the aisles for an hour — sweating bullets — before finally returning home to announce "she was flattered, but unavailable."

The next day he returned fire by challenging me to do paperwork (I'm notoriously incapable), but I managed to actually get it done.

I challenged Jamian to invite a group of students from the college dining hall he regularly snuck into back to dinner at our house, he challenged me to write a poem about a stranger and read it to them aloud.

I challenged him to build a snowman in the front yard of someone he didn't know's house, and he responded the next day by challenging me to start a snowball fight with a stranger.

This was probably my most difficult challenge. I biked down to Shenley plaza, a spot in a college neighborhood of Pittsburgh that gets a lot of foot traffic, initially confident that I'd knock the challenge out pretty quickly. At first I tried standing on the sidewalk with a snowball in one hand, eagerly (and then later dejectedly) asking passers-by if they would like to be part of a snowball fight. For this, I was met almost exclusively with ridicule and derision. "Uh, I'm good dude." "Yeah, uh... no thanks, buddy." Some people would politely decline, but nobody accepted my offer.

After 45 minutes, I thought "fuck this," and just started randomly pelting people on the sidewalk with snowballs. But do you know what happens when you randomly hit someone in the face with a snowball? They don't throw one back. In my experience, they'd yell from a distance, run the other way, or perhaps most ridiculously, pretend that nothing had happened. Not a single person, however, even appeared to think about reaching for a snowball to throw back. An hour passed, and I became more and more frantic with my snowball assaults, but no snowball fight emerged.

I decided to try a different tactic, and found some outdoor tables from a summertime outdoor cafe, which I drug next to the sidewalk at 20 yards apart. Then I built a big pile of snowballs for each table. I would stand in between the two tables, waiting for someone to come from either direction, and then run to the table opposite the direction they were coming from. Just as they walked past the table full of snowballs, I'd lob one at them from the other table. My hope was that, given a perfect collection of ready-made snowballs, they might choose to return fire.

But again, most just chose to turn around and run the other way.

So I went further and drug the tables directly into the center of the sidewalk, then built a small snow barricade around them. Just getting past the table was difficult now, and I finally timed it perfectly such that I hit a group of college kids with a snowball right as they were coming up to the blockade. They looked at the shrapnel of the broken snowball around them, their eyes rose in unison to look at me, and the pile of snowballs caught their gaze intead. They looked at me, back at the snowballs, then back at me. Something clicked inside their head, and a snowball fight finally began.

At last, after three hours of standing in the cold, the challenge was met.

I felt as if the stakes had gone up, so the next morning I met Jamian in the kitchen and asked if he was ready for his challenge. "Attend a Jewish religious service," I said, while pausing to prepare him for the gravity of what was to come next — "...and sing."

Jamian had a friend teach him some hymns, and the two of them posed as a visiting couple at Pittsburgh's Rodef Shalom Synagogue. His anguished voice stumbled through the lyrics, while he no doubt mentally plotted future challenges to avenge that awkward moment.

The challenges continued. I had to bake something I'd never baked before, compose a piece of music (which briefly became a Pittsburgh dance party hit), and sneak into a sauna.

One morning I challenged Jamian to paint a self portrait. Later that day, Jamian, who'd never drawn anything before in his life, rummaged through our free box, found a blank canvas and some kids paints, and disappeared for a few hours. The self portrait that he returned with was clearly him, and even featured his signature goofy grin, but it appeared to be drawn by a third grader. Over time, however, it really began to grow on us, and I'd often find houseguests transfixed by it.

The most embarrassing challenge I got was "ask a stranger in a gym out on a date." There's just something about the combination of dating and gyms that creeps me out. I can't imagine how anyone manages to hit on anyone else in that setting without feeling completely ridiculous.

I didn't have a gym membership, but rode my bike to the nearest gym and simply walked past the front desk. Once I'd gotten in, the scene was even worse than I imagined. While the place was pretty full, there wasn't any music playing, and nobody was talking. Basically, it was a packed room that was absolutely dead silent. Additionally, every woman in the place was (smartly) wearing headphones, leaving no opportunity at all for casual conversation.

So I was coming to terms with the idea that I was going to have to wave someone down, get her to take out her headphones, and then ask her out on a date straight-up while every other person in the place heard the whole exchange in crystal clear fidelity.

That seemed pretty grim, but I discoverd that the lower level of the gym was all treadmills and "elliptical machines." Strangely, each of the machines had individual TVs mounted to them! This room was also completely silent, but there was at least some background noise from everyone running, which was a slight improvement over the absolutely dead silence that I was staring down before.

The only open machine was next to an attractive woman my age who appeared pretty invested in whatever was happening on TV. So I got on the available elliptical machine and started swooshing. This lady was obviously not in any mood to talk, so I decided that I'd just have to go straight for it. Finally I said "Hey," while trying to sound cheerful. She slowly turned her head from the TV screen, looking over at me. "Think you might want to go out some time?" I asked point blank.

Without saying a single word or displaying any emotion at all, she just turned her head back towards the TV and continued watching what she was watching before.

I chuckled, got off, and fled into the night a few minutes later, the challenge met.

The end of challenge-a-day also coincided with Jamian's last day in Pittsburgh. His bags packed, our farewells almost complete, I asked "are you ready for your final challenge?"

I produced a folded slip of paper from my pocket, the final challenge being that he had to give this note to a woman his age in the airport, without first reading the note himself or qualifying the exchange by explaining that he was completing a challenge.

At his layover in Philadelphia, he nervously walked through the airport before sitting down next to a punk woman headed to Houston. He tentatively started a conversation before producing the note from his pocket, awkwardly holding it out in the palm of his hand. "Uhm," he asked, "could you read this?"

The woman took the note, as Jamian's mind raced with all the possibilities of what could be written on it. Airports are dangerous places for people like him and me these days, and distinct visions of being hauled off by security guards flashed through his mind. Finally the woman opened the note, laughed out loud, and exclaimed "me too!"

"Wait, could I see that?" he asked. The woman gave him a confused look before handing it back. On the note, I'd simply written "I'm wearing pink underwear!"

What's amazing is that he was actually wearing pink underwear. He had one pair, which I'd never even known about, that he chose to wear that day.

It was a great month.

Julian

Above: My housemate's self-portrait. He's obviously never painted anything before, and while this does appear to be done by a 3rd grader, it has some kind of unusual draw that really grows on you over time. While it was up, people visiting our house would find themselves strangely entranced by it.