For those of you who don’t live on the East coast, it was a rainy weekend out here.  New York always seems a little more in touch with its gritty side when it rains.  Everything seems to slowdown and everyone seems a bit more introspective–like a private detective in a dime store novel.  I crashed at Kate’s place Friday night and so found myself spending a lazy rainy Saturday at my girlfriend’s apartment on the Upper West side, trying to think of something to do.

“I’m in the mood to play Monopoly,” said Kate.  I was taken aback, not because of any sort of dismay on my part—I have a love of board games that every only child is cursed with and have spent most of my adult life trying to make up for all those lost nights of rolling dice and plastic pieces.  In college, I organized semi-regular sessions of Clue, Jinga, and Scene-it with my friends disguised as pregamming parties before heading out to the bars.  It was just that Monopoly was never my game. It was one of those games I always lost.  Maybe it’s because I lack any real serious financial know how (It seems I’m always trying to beat out a paycheck). I don’t think I’d ever even finished a game of Monopoly in my life.

I purposed playing Scrapple or Trivial Pursuit, but Kate had her mind set on Monopoly.  After I explained how I wasn’t wild about it and that “I always sucked at that game,” she eyed me much like a predator eyes her prey.  And so we were off on a mission to find the Parker Brother’s classic.  In the pouring rain—Kate’s dog, Marshall, in tow—we searched for a copy of the game.  It took us nearly an hour to find one, get back to the apartment, dry off, and set the game up.

The first game went about as well I remembered.  I bought pretty much every property I landed on and could afford, rolled with my fingers crossed, tried my best to save money, and Kate kicked my ass.  During my last roll, I landed on Park Place with a hotel on it and I had $50 left in toy money.  I threw my cards (deeds for my meager properties) across the table with a “take it” and sulked.  In between pouting I reiterated my hatred for the game and how I always managed to lose.  “Babe,” Kate said, “You’re being a sore loser.”   To which I responded, “Well, you’re being a sore winner.”   Yeah, I know—that doesn’t make much sense.

About thirty minutes later, she somehow talked me into another round and went off to get something to drink.  I took the few minutes I had alone with board game (which was mocking me with it’s tiny houses and hotels) to study it and try and develop a strategy.  I realized that if I focused on buying high-end properties around the corners (ignoring low cost land, railroad, and utilities) and building houses first , I could create an income to expand my holdings.  Around then Kate cam back into the room and asked if I was ready for round two.  “Yeah,” I said.  “I think so.”

And you know what, dear reader?  My victory was glorious.  I was shrewd, I had foresight, I was quick to act, and most importantly—I had great luck.   Here’s a picture of the end of that game, all the houses and hotels are mine:


And that’s how I won my first game of Monopoly.