The first and only time I’ve ever gone to Key West was with the Feldman’s when Casey and I were 16 years old. Casey brought me along and Brett brought Jason Spector. We had planned to stay there for about a week but after only a few days all tourists were told to evacuate the island because of an approaching hurricane. Not wanting to end our vacation early, the Feldmans booked a room in Miami at the Lowe’s Hotel right on the beach. During the day, Casey and I were allowed to go off on our own and sit by the pool while Aunt Dianne and Uncle Joel did whatever the boys wanted to do.
Taking advantage of this new freedom, Casey and I decided to try to get non-virgin pina coladas from the bar by the pool. To avoid the awkwardness of being denied this coveted drink, Casey and I came up with a plan. After a short conversation we decided that out of the two of us I looked the oldest and would have to be the one to order the drinks. Casey and I went up into the hotel room, took one of Aunt Dianne’s straw hats and applied red lipstick, hoping I would look even older with these accessories. Once we got back down to the pool my nerves started to kick in and I told Casey that she would have to order the drinks, that we could go back up stairs and put red lipstick on her instead (because apparently redlipstick = old enough to drink). But Casey never let me back down, and told me that I had to order the drinks and to stop being a cow.
Finally, I got up enough courage to ask the bartender for 2 pina coladas. He looked at me for a second and then asked for the room number. Excited that our plan had worked, I quickly blurted out the room we were staying in and that it was probably under the name Joel Feldman or Dianne Anderson. Once the bartender returned with our drinks Casey and I went back to our lounge chairs for our first sip of a “real” pina colada only to discover that it contained no alcohol. It was, in fact, a virgin pina colada.
After all our hard work and preparation our plan had failed!
[To see more photos from this vacation click here.]