Date 11 - The Strategist (Part 1)

  • The Scene: Poolside Party.

  • The Attire: Black bikini, black shorts, white cover-up hooded top, and black flip flops.

  • The Meeting: We met briefly the night before, but it was short and uneventful. The next day, I was introduced to four male friends by our concierge service to share a ride to and from a party that was a long-haul distance from the hotel. The Strategist was one of these four gentlemen. While at the party, we engaged flirtatiously, but it was nothing to write home about. Then, the song, this song, an incredibly thematic one with a phenomenally catchy beat called “Pick up Something,” captivated everyone, including me, and he, this Strategist, picked me up! He carried me from one end of the venue to the other, all while being soaked with the vibes of this insatiable Trinidadian themed song. I mean, somebody!

  • The Environment: Spirited, electric, easy, and colorful (pool on one side and the open water on the other).


On arrival at the venue, I made a decision to leave the gentlemen to do their thing and not be impacted by the fact that this “female” caught a ride and is now hanging around. I got food, took great pictures, got a poolside massage, and rocked to the incredible tunes that were blurring across the waves. 

I don’t drink and hadn’t consumed anything the entire time I had been on this wonderful island. So, I began to think to myself (silently, of course), “I fly back tonight on the redeye (midnight) – it’s a day party – sooo let me have a small sample of this infamous rum that was heavily promoted and primed for the taking.” Combine the massage, the rum, and the atmosphere, especially after playing “Pick up Something,” the flirtatiousness escalated. The energy was apparent, the attractiveness obvious, our chemistry was inexplicable. He looked at me as if he only saw me, and that is a remarkable emotion to bask in. He asked me if he could come to Atlanta to visit, and I said, “We will see.”

 Together, all five of us got a taxi back to the hotel. The Strategist waited with me until my taxi to the airport arrived, placed all my bags in the car, and we bid one another a sweet farewell.


  • Note to Self: Never underestimate how and where a connection can happen. 

  • Shout Out to Men: Be bold and claim your heart’s desire. 

  • Question: Why is living in your own head so easy?

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Date 10 - The Dude

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Date 09 - Willie Wonka and All That Chocolate