Craziest Bet You Have Ever Made

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  • Casperwaits
    SBR Hall of Famer
    • 08-25-06
    • 5042

    #1
    Craziest Bet You Have Ever Made
    I know we all have made dumb bets, drunk bets, chasing bets, but what I am talking about is a bet that might not have been for money or a bet that was not on a traditional situation or setting.

    For instance, as I was working on my screenplay today, I remembered a bet I had made as a freshman in High School. The year, 1989. Tenafly, NJ. I was a gangly and awkward kid trying to find his way in the rough and tumble world of BMW's and Mercedes'. Our school was very well off financially, so every year they held an Olympic themed day for all students. The kids were seperated by grades, and competed against each other for bragging rights. The one signature event was the Pie Eating Contest. Now, as I have gotten older pie eating has become one of my favorite activites (pun intended), at that time not so much. Even though I knew I had no chance of winning I bet the 3 time winner that I would beat him in the aformentioned contest. The bet was that if I had won, he would get me a date with any girl in the school I wanted. I know, I know that sounds far fetched, but this kid was pursuasive. If I had lost I would have to sing to the girl of his choosing. With the contest looming, word got around quickly that the challenge was on. Day of the contest, my morale and vigor had never been higher. As we sat in front of the pies I felt like I had a chance...a snowballs chance, but a chance nonetheless. To make a long story short, I lost by literally a hair. The three time champion was adept at putting most of the pie in his. Suffice to say a week later I was on my knees in a Top Gun styled outfit singing "You Lost That Loving Feeling" to the HOTTEST senior in the school in front of 800 kids. Looking back on that bet I consider it a pyrrich victory, for without it, I may never have gotten the chance for a girl of that caliber to even talk to me. After that contest her beauty was only surpassed by her sweetness and friendship towards me. Sometimes losing a bet is not so bad.
  • TPowell
    SBR Posting Legend
    • 02-21-08
    • 18842

    #2
    sounds like a win-win to me lol
    Comment
    • jjgold
      SBR Aristocracy
      • 07-20-05
      • 388179

      #3
      I actually bet a beat up house I inherited to a bookmaker and lost the bet like an asshole
      Comment
      • fiveteamer
        SBR Posting Legend
        • 04-14-08
        • 10805

        #4
        One time I was drunk and bet $100 into the Canadian Cal Expo win pool at 2 am, there was about $300 total.
        Comment
        • SlicWilly3
          SBR Wise Guy
          • 11-05-08
          • 607

          #5
          I was up around $3000 in my Betjamaica acct and decided to do a $100 parlay for fun. $100 to win around $10,000
          I took 8 games and won the 1st 7. Came down to the Marlins beating the Braves....
          They lost ........ Sucked.
          "Success doesn't just happen, it happens for those that take action"
          -Donald J. Trump
          Comment
          • robmpink
            SBR Posting Legend
            • 01-09-07
            • 13205

            #6
            I was up $13,000 at Canbet in 2000. I then lost $3,000. I was going to cash out. Before I did so, I bet $5 or $6,000 to win a $1,000 on an aussie rules game I knew nothing about (money line). I won then cashed out the next day for $11,000 minus bank wire fees.
            Comment
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