Long Term Bets

My favorite bets to make are long term, low stakes bets. Half the fun is remembering you even made the bet.

My second favorite long term bet was one I made with my brother Brian. I can’t remember when we made the bet, but I am pretty sure I was in high school. I bet Brian some tiny amount of money (5 dollars maybe?) that he would not be able to dunk a basketball. I may have put a time limit on it (before he graduated college?) though I am not sure.

All I remember is Brian proudly coming up to me to tell me he did it. Admittly he barely did it and I never saw it. But the low stakes guarantees the lack of a need for him to lie.

That’s a lot of fuzzy details – but the reason I loved this bet is that instead of paying I made it double or nothing that he’d be able to do it again. He agreed.

I never paid that bet.

The reason its not my favorite bet is that I was betting on Brian failing at something.

My favorite bet is with Sean Taylor and Matt Pack. We were at a Mets game a few years back and we watched the ceremonial first pitch before the game started. I talked about how cool it would be to do that.

Quickly we made a bet that if one of us ever got to throw out the first pitch at a baseball game the other two would shave their heads into a mohawk.

Despite the fact that the bet may never be won we set a few guidelines in place. It had to be a for a major league game (a minor league single A game seemed too attainable!) And the loser’s had to wear the mohawk for a significant amount of time. I don’t think we set a firm time, but I’d figure a week at least would be fair.

I sort of hope one of us wins this bet.

Matt might be the closest as he is currently writing about baseball for True/Slant.

Though if he plans on winning the bet he’d better hurry before I lose enough hair to be unable to grow a mohawk.

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3 Comments

  1. Brendan
    Posted 7/21/2009 at 1:23 pm | Permalink

    I made a bet a few years ago with a co-worker that I will never get married. It was a stupid bet because I only win when I die unmarried.

  2. Brian
    Posted 8/19/2009 at 7:36 pm | Permalink

    I never dunked a second time. But once was pretty cool.

  3. Brian
    Posted 8/19/2009 at 7:36 pm | Permalink

    And, it was a single dollar.

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