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Playing Dress-Up in Greenwich, Connecticut

*** This is an excerpt from my book about failed relationships coming out at the end of the year!

I remember when I was in elementary school one of my friends told me that when she was on vacation in Disney World if someone asked where she was from and she told them she was from Connecticut, they immediately assumed she was rich. I was perplexed. She had an in-ground pool but certainly didn’t live in a gated community. Our families were predominately from Waterbury, Connecticut, a remnant of the long-gone industrial era.

I discovered when I went to an out of state college that what she said was true, that when you tell people you are from Connecticut they assume you live in a neighborhood on par with one of the most affluent ones in Greenwich. Years ago I had never been to Greenwich and wondered what this place was like. The richest town in the entire country would surely be something to see. I imagined that I would be pegged an outsider from the second my 2001 Kia Sportage crossed over the city limits. I was very wrong.

I got a job working for a holistic beauty company and had to go to various health food retailers. Now I had to drive down towards the Gold Coast for work at least once a month. My first experience there was good and it really hasn’t changed since I began working in that area.

One day I answered an ad on Craigslist. They needed bartenders and servers. I sent them my resume and a picture and was hired immediately and asked to come down the next day. Not only would I be bartending in Greenwich, but on a yacht! I would be lying if I told you I was excited. No, I reacted as I usually do when something really great and exciting happens in my life: I was terrified! I had never answered an ad on Craigslist before and feared it wasn’t legit. A yacht? Really? As usual, I pictured worst-cases-scenarios in my head; the yacht taking off with me and other unsuspecting young “bartenders” on it, carrying us out to sea awaiting some sort of mass-auction, our introduction into sexual slavery. Yes I know, I don’t deny that I’m a little crazy. I lived on the Mexican border for a year and never ventured south for the same reason. It’s funny, how someone who has lived to tell the tale of so many risky and dangerous events can be so scared and cautious. I would wager that it is because I lived to tell the tale of so many risky and dangerous events!

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