There is a Pittsburgh punk tradition called "Fun-A-Day." For the entire month of January, participants of the "Fun-A-Day project" 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. At the end of the month, there's a party where everyone gets together to present their fun-a-day.

Picking your fun-a-day can be a challenge. Just like a job that might initially seem enjoyable, but which inevitably becomes insufferable due to its 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 this year my housemate and I decided that we'd like to do something together. We thought that by alternating days we might lessen 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. This seemed like a great plan, but neither of us had ever been on an internet date before. So in the week leading up to January, we scoured craigslist and signed up for every online dating site we could find. We literally blackened the skies of the internet with messages and responses to ads in an attempt to schedule enough dates in advance.

In that week, neither one of us were able to successfully line up a single date. I had this conception of internet dating as some magical place where the dates flowed freely, but boy were we wrong. We might have made some headway had we perservered, but the whole thing was really a lot more work than we anticipated.

So on January 1, 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. You had to complete the challenge by the end of the day, and if you couldn't, you had to buy the other person an Indian buffet. (For some reason, Indian buffet had become the common currency for all bets in our lives. To buy someone an Indian buffet had become almost insulting in its implications.)

The challenges ended up being kind of amazing. They were often borderline brutal, but you couldn't go too crazy, because you had to temper your challenge with the knowledge that you were going to get one back on the very next day.

Most Difficult Challenge

The most difficult challenge I got was "start a snowball fight with a stranger." I biked down to Shenley plaza, a spot in the college neighborhood of Pittsburgh that gets a lot of foot traffic, sure in the knowledge that I'd knock the challenge out pretty quickly.

At first I just tried standing on the sidewalk with a snowball in one hand, eagerly (and then later meekly) asking passers-by if they would like to be part of a snowball fight. For this, I was met with nothing but ridicule and derision. "Uh, I'm good dude." "Yeah, uh... no thanks, buddy." Some people would politely decline, but nobody accepted my offer.

So after 45 minutes of that, I thought "fuck this," and just started pelting people on the sidewalk with snowballs. 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 happened. But not a single person 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 into 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.

Instead, most 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 someone with a snowball right as they were coming up to the blockade. Something clicked inside their head, and they pretty furiously started unloading on me from their table.

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

Most Embarrassing Challenge

The most embarrassing challenge I got was "ask a stranger in a gym out on a date." Asking someone out cold on a date is always a little difficult, but I find the gym setting to be particularly unappealing. I know that the gym is supposed to be a major pickup spot or something, but the whole environment is so gendered to begin with that I just can't imagine how anyone manages to chat someone up while actively lifting dumb-bells, without feeling completely ridiculous.

I also didn't have a gym membership, but that didn't actually turn out to be much of an obstacle. Once I'd gotten in, it was even worse than I imagined. The place was pretty full, but (to my surprise) there wasn't loud music blasting, and nobody was talking. Basically, it was a packed room that you could hear crickets chirping in. Even worse, every woman in the place was (smartly) wearing headphones.

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

That seemed pretty grim, so exploring a little more, I discoverd that the lower level of the gym was all treadmills and "elliptical machines." Strangely, each machine had individual TVs mounted to them! This room was also quiet, but at least there was the background noise of everyone running rather than 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, but wasn't wearing headphones. 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 with a serious totally inconsistent with what I was attempting.

Without saying a single word, she just turned her head back towards the TV and continued watching what she was watching before.

I shook my head at myself, got off, and fled into the night a few minutes later, the challenge met.

The Complete List

The list of challenges I gave my housemate:

(We'd been somewhat enthusiastically sneaking into the University of Pittsburgh dining hall during these months, so some of the challenges revolved around that setting.)

1. Ask a stranger out on a date in Whole Foods.
2. Successfully invite someone from the Pitt dining hall back to dinner at our house.
3. Attend a Jewish religious service, and sing (he's not Jewish).
4. Build a snow man in a stranger's front yard.
5. Run on a tread-mill.
6. Do 100 pushups over the course of a day.
7. Paint a self portrait.
8. Start a dance party in the Pitt dining hall.
9. Give a sealed note that I'd written ("I'm wearing pink underwear") to a woman his age at the airport, without knowing what was on it and without explaining that he was merely meeting a challenge.
10. Surrupticiously install the self portrait he painted on the wall of an art gallery.

The list of challenges he gave me:

1. Do paperwork of my choice (I'm notoriously incapable of doing this).
2. Write a poem about a stranger and read it to them aloud.
3. Attend an Orthodox Synagoge with a friend of ours, posing as her boyfriend for the older Jewish women there.
4. Start a snowball fight with a stranger.
5. Get into a hot tub, sauna, or steam room without paying.
6. Bake something I'd never baked before.
7. Compose a piece of music.
8. Ask a stranger out on a date in a gym.
9. Get fired from a job.
10. Audibly fart in a crowded elevator.

It was a funny month.

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.