Rich Kids Make Outrageous Bets in the Hamptons

Big Duck, Rich Kids OutrageousBets
Wanna bet? Photo: Gen Horsburgh,

My neighbors Mike and Dottie took their daughter and a couple of her friends to Europe the second week of September. Their son Jason stayed behind with four of his fraternity brothers (I have no idea how they avoided attending school) and decided to spend almost the same amount of time at his parents Southampton home.

As a favor to the parents, I consented to keep an eye on the young man and his friends, so they did not get into any real trouble. Somehow this morphed into my keeping a diary of their antics. Perhaps this could be used as a basis for a new television show titled Rich Kids Doing Outrageous Things in the Hamptons.

Each of the antics involved bets. They are in no particular order and, for God’s sake, DO NOT TRY THESE AT HOME!

1. All subjects decided to have a paddleboarding competition. The basis of the competition was to see who could remain standing on the paddleboard for the longest period of time while in the water without falling off. To make it more challenging, each person had to down five shots of Jack Daniels prior to commencing the challenge. Subject #3 won with a time of 17 minutes and 5 seconds.

2. All subjects decided to have a selfie competition. The first person to return to the house with a selfie of themselves and a squirrel in the same picture would be declared the winner. Subject #2 somehow was able to accomplish the challenge and returned with a selfie of himself and not one, but two squirrels in the same picture.

 3. Subjects #1, 2, 3 and 5 bet subject #4, who is a competitive swimmer, that he could not swim 20 laps in the pool within 30 minutes. The only caveat was that his ankles had to be zip tied together. Subject completed the task in less than 17 minutes.

4. Subject #1 bet subjects #2, 3, 4 and 5 that he could walk from the Big Duck in Flanders to the fire department in Hampton Bays in 3 hours. The challenge was made more difficult by the fact that he was required to wear full scuba gear—including swim fins. Subject did not make it to the fire department in the allotted timeframe due to the fact that his scuba tank ran out of gas before his arrival.

5. All subjects agreed to a bet to be paid to the first person who could catch a live fish with their bare hands. The challenge took place in a tidewater pool at Reeves Bay. All subjects were unsuccessful at the challenge. Subject #5 did cut his foot and was transported to the emergency room for stitches and a tetanus shot.

6. Subject #3 bet subjects #1, 2, 4 and 5 that he could get the very aggressive pit bull that resides in the fenced front yard of the house at the end of the block to lick his face. Subject departed house with a jar of gourmet peanut butter and the remaining subjects close behind. Said pit bull was unreceptive to peanut butter ploy and subsequently removed part of subjects shirt with his teeth.


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