let's talk about Monopoly.

Monopoly is just one of those games: you love it or you hate it. It should be no surprise to hear that I love it – after all, why would I write a blog story about a board game if I didn’t like it?

My dad taught me how to play Monopoly (my mom falls unapologetically into the “hate it” camp). I’m sure it was during a blizzard, as that tends to be the only time my dad and I play Monopoly. As anyone who has ever played Monopoly knows, the game can be a real time-suck. Plus, it’s bad form to just give up: you must keep playing until the bitter end. When my brother and sister got old enough for Monopoly, they’d enthusiastically accept an invitation to start the game, but they would rarely finish. I guess they just hadn’t yet developed the thirst for fake capitalism and heartlessly bankrupting your family members.

There is one thing you need to know about playing games with my father: he will mock you mercilessly. No one is safe from Dad’s snark; he’s an equal opportunity ridiculer. Even if he’s losing, Dad will continue with sarcastic comments until the very end. The game you’re playing doesn’t matter: from Monopoly to cribbage to tic-tac-toe, every game played with my dad is infused with derision. As long as you can insult him right back, you’ll be just fine.

Anyway, playing Monopoly with Dad is how I first learned the fine art of good-natured taunting. It’s critical to be able to do this to be a member (in good standing) of our family. Dad, my brother Mitch, and I come by it naturally, but kinder souls like my mother and sister have to work a little harder. James, my fiancée, is nicer than all of us, so it’s taken him almost eight years (can you believe we’ve known each other that long?!) to be able to tease with the rest of us. He’s not yet up to Dad’s, Mitch’s, and my level, but we’re hoping that James will just keep practicing.

I keep getting side-tracked. Back to Monopoly.

My cousin Dana was (and probably still is) a Monopoly aficionado. He would come from California to visit in the summer, and we would always play a game or two of late-night Monopoly. One such game has gone down in family legend: Dana and I were neck and neck, and we played into the wee hours of the morning. I think we may have had hotels on the entire board, and the properties were pretty evenly split between the two of us. The game showed no real sign of ceasing until, at long last, the bank ran out of money. We had reached an impasse. No longer able to play our game (and not feeling ambitious enough to mint some new Monopoly money), we totaled our assets to determine the champion. Dana ended up winning, but by some ridiculously small margin like two hundred dollars. That, my friends, was a GAME.

This is not that game, but it's a Monopoly game with Dana all the same.

Another favorite do-or-die Monopoly story is from a snow day I spent at my friend Allison’s house. I had spent the night at my friend Allison’s house, and an overnight blizzard had us snowed in the next day. Allison and I played a six-hour game of Monopoly with her dad. Allison was the first one to go bankrupt, but I hung on for dear life. Sadly, my railroads and few prime properties (Boardwalk and Park Place; Pennsylvania, North Carolina, and Pacific Avenues) were no match for Frank’s: he owned the purples (Mediterranean and Baltic), the light blues (Oriental, Vermont, and Connecticut), and the pinks (St Charles, States, and Virginia). He was the slumlord, and the Community Chest and Chance cards worked in his favor: the “advance to Go” card set you on the brink of his string of properties, and the “advance to St Charles Place” card put you right in one of his hotels. It wasn’t long before I foundered, but I fought nobly… or, at least that’s how I remember it, so that’s what I’m telling you.

The last truly memorable Monopoly game I played was during my freshman year of college. As a college student, I didn’t play a whole lot of board games. There are two reasons behind this: 1.) I was always quite busy (and sometimes, I was even doing schoolwork!), and 2.) nobody really wanted to play board games. My college friends tended to have better things to do, like drink beer and… drink more beer. This game of Monopoly came about only because said friends wanted to make a drinking game out of it; hence, “Drunkopoly” was born.

Now, I’m not just saying this to make you think I’m some sort of paragon of responsible choices, but I didn’t drink during Drunkopoly. This game was on a weeknight, and I’ve never been a fan of weeknight drinking (unless you have the following day off, of course). There was only one other sober person playing that night, and it was none other than James! This was well before we were a couple: at this point, we had another year-and-a-half of friendship to go before we began dating. Nobody else was really into the game, but James and I had a great time. I don’t remember who won, but I distinctly remember James offering to shave his mustache off if I’d trade him New York Avenue. (I didn’t take him up on his offer, but I really should have: to this day, James insists that he would’ve honored the deal.)

You can't see the Monopoly board, but I promise, it's there.

My Monopoly career has not been restricted to the board game. For Christmas one year, my parents gave me the hand-held electronic version. 

Let me tell you, that hand-held Monopoly game got me through countless road trips and stints in the waiting room at the orthodontist. It was really kind of ridiculous; the game had all these dorky characters you’d play against (the only one I remember was named Diamond Jim), and there were even goofy sound effects (like a train whistle when you landed on the railroads and a booming noise if your token was the cannon). It’s been years since I’ve played hand-held Monopoly, but I bet I could still find that game buried deep at my parents’ house. I should probably start bringing it for my lunch breaks at work… but only if the “mute” button is still functioning, as no one wants to hear Uncle Pennybags’ narration.

The final component of my Monopoly trifecta was the Monopoly computer game. I don’t remember a whole lot about the game… except for one incident where I asked my dad to watch an auction for me while I ran upstairs. In this version of Monopoly, properties were auctioned off if whoever landed on it declined to buy it. I wanted to buy whatever property was being auctioned, so I stationed Dad there to guard it. From downstairs, I heard Dad yell, “Calla! You’re going to lose the auction! Marvin Gardens is about to be sold for a DOLLAR!” I bolted down the stairs, only to slip on the rug at the bottom and go crashing into the wall. Dad laughed like a hyena, but dammit if I didn’t win that auction.

Whenever I played Monopoly, there was never a certain token that I HAD to be. Dad was always the car, and Darrah was always the dog. Me? I like variety.

I’ve never gotten to be the car (because I’m almost always playing with someone who demands the car), but I’ve tried all the others. I was particularly fond of the battleship (because it’s badass) and the thimble (because seriously, what is a thimble doing there?). And I don’t know about you guys, but I was bummed when the American public voted to retire the iron. The iron was one of my favorites, thanks to its handle. I’m not going to stress about it too much, as I’m sure the Iron Police aren’t coming to confiscate the token from my game.

I’ve lusted after a few specialty Monopoly boards (Lord of the Rings Monopoly and A Christmas Story Monopoly come immediately to mind), but I’ve never made the leap and bought them. It’s just as well: I don’t think anything could quite compare to the original. What a wonderful feeling to FINALLY land on that last color blocked property you need to create your Monopoly. And it’s pretty damn great to watch your opponent (especially when you’re playing against someone as cocky as my dad) sell of their little green houses and scrape together just enough cash to take care of the bill… THIS time. On the other hand, nothing strikes fear in the heart quite like approaching a cluster of bright red hotels that don’t belong to you… and then the grim realization that you have to mortgage your precious railroads to make it to your next turn. It’s exhausting.

It’s been years since I’ve played a game of Monopoly (maybe it was my four years at a liberal arts school?), so it’s about time to get back in the Monopoly saddle. Next time we’re looking for something to do, I’ll see if James is up for the challenge. I’ll even let him be the car.