Week 13: Gamble

No one will play Monopoly with me anymore.  I suppose it’s fair – I tend to get insanely competitive.  There’s just something about that game that forces me into an alpha male state.  It must be the trading aspect.  Much like poker, you can win Monopoly entirely on the strength on your ego.  If you’re a good bully, it doesn’t matter what comes up on the dice.  I’ve certainly taken the bully role to heart.  I went to beach week after college with some friends and one other person I had never met before.  We all played Monopoly together on the first night.  The new person didn’t say a single word to me for the remainder of the trip.


When my friend Matt volunteered to take me to Atlantic City for the gambling challenge, I was thrilled to be adding a patch to my man scout uniform in Monopoly’s birthplace.  It just seemed right.

I’m not a novice at gambling.  I entered college just as the poker craze hit its apex and had a weekly game with the guys on my hall.  I was a decent player – I rarely let my emotions get the better of me, and I was smart about when to take risks and when to lay low.  But I’ve always seen playing a low-stakes game with friends as a totally different beast than gambling at a casino.

The most I’d ever done in a casino was play a few slot machines on my honeymoon cruise.  Though I was familiar with most casino games through years of playing Hoyle Casino on the computer, I was under the impression that it doesn’t take long to lose a few hundred bucks and frankly, I don’t have that kind of money to burn over a quick thrill.

Still, I was intrigued and knew I was in good hands with Matt, who has done his fair share of casino gambling.  Matt and I met in our first year of college, and by senior year, we were hosting the weekly poker game.  Not surprising for a math major, Matt makes his moves with careful consideration of the odds and has always been a smart player.  As a logical person myself, I figured I could take his cues while in Atlantic City without fear of regret.

On the drive from Manhattan to our hedonistic destination, Matt lays out his three big commandments for gambling without losing your shirt:

view from car
  1. Accept that you are going to lose.  Matt says the money you put down in the casino is no different than the money that goes towards a Broadway show or nice dinner.  You’re paying for entertainment, not making an investment.
  2. Don’t bring your ATM card and never go to the ATMs.  Set the amount of money you feel comfortable losing and don’t go over that amount no matter what.  After some deliberation with co-workers and gently persuading Q that this money is an investment in my manhood, I decided on three hundred dollars.  I feel vindicated when I see that Matt has brought the same amount.
  3. At every table game, play until you double your money, lose it all, or get bored.  Matt advises me to start with eight to ten times the bet limit at each table.  I tell Matt that I’m worried this method will result in losing a hundred dollars in ten minutes, but he assures me that table games take much longer than I would expect, especially in games like craps and roulette.

Matt further elaborates on other tips of the trade, like to never comment on anyone else’s playing style and to always get a free drink when you sit down at a table game.  I ask him if those big three commandments were common sense to him or if he only learned them after making some costly mistakes.  He says everything was second nature except for the fact that when you’re down in chips, you’re still spending for entertainment, not trying to win your money back.  I’m hoping I can learn from Matt’s advice and not have to make my own mistakes.  But I know that’s never been my way.

Want to read more? You’ve reached the end of the preview, but the full text of this entry and many more can be found in my book, BE A MAN: How I Spent One Year Drinking, Shaving, Farming, and Fathering My Way Toward Masculinity.

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