Jen and I have been making bets on Flickr photos since we first became friends in 2006. It started when we noticed a ton of photos on Flickr from large scale public events like Newmindspace pillow fights and bubble battles, roving street parties like One Night of Fire, and crazy costume processions like the Mermaid Parade. We would attend these happenings and then bet on how many photos from the event would be up on Flickr by the end of the week tagged with an obvious, agreed upon tag. Whoever was closest won a free drink from the loser the next time we hung out.

The game was both a criticism and celebration of NYC's penchant for over documentation of public space spectacles. It was also a way to not take that last sentence too seriously.

In 2007 we had an idea to become a part of the game! We would choose a sure-to-be over photographed happening, then the two of us would don shirts with the text "Tag me on Flickr as JasonWinsTheBet" or "Tag me on Flickr as JenWinsTheBet". The main rule would be that we couldn't offer unsolicited explanations of the bet. We could only tell people about it if they asked first. And no bribing! At the end of the week, whoever was tagged the most received a free dinner from the loser!

At Burning Man later that year, Jen rolled up with a surprise. Her mom had made the shirts for us! Awesome! They were even pink and blue like the Flickr logo! We agreed to tuck them away until we could find the perfect event at which to unveil them.

Fast forward two years. Newmindspace was planning a "People photographing people photographing people" meta-event at South Street Seaport. PERFECT. We showed up and started snapping our own photos. People caught on pretty quickly.

Unfortunately, no one had taken into account that humans are not flat, but in fact, cylindrical, and my tag—JasonWinsTheBet—which is two characters longer than Jen's tag—JenWinsTheBet— was often lost under my arm pits or just partially obscured by my slender physique.

Jen ended up winning the bet 5 to 0 because of these flaws, but maybe also because she's prettier to look at. I took her out for dumplings and tried not to gnash my teeth too much. After all, this was only round one.

I think we'll submit this to Conflux next year. Hopefully I can convince Jen to wear the shirts all weekend, and then the loser has to buy drinks not just for the winner, but for everyone who tagged the winner on Flickr!