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Relationships

Sail, Sail Away

Ray told me to meet him at the yacht club right after work on Friday. It was a gorgeous, sunny day barely a breeze in town. If I could hurry up and get there by 5:30, he and a few others were departing for a short sail. If not, no worries, he would leave a guest pass for me at the front desk with carte blanche for anything my heart desired at the bar.

I felt out of place as soon as I arrived, driving my beat-up Honda Civic into a parking lot full of shiny Bentleys, Beemers, and Volvos. I collected my guest pass and made my way into the main room. I should have felt quite at home with so many Filipinos around. But I’m sure the Trumps were wondering what I was doing ordering a drink…I should have been serving alcohol behind the bar with the rest of my people.

Ray finally arrived. What a relief. We had a great time chatting and he proceeded to introduce me to everyone there that he knew. Everyone was actually really nice. We continued to drink and ended up having dinner there. It was probably the most perfect date I’ve ever been on: great view, good people, seamless conversation, yummy food…I couldn’t have asked for more.

We both agreed we had a great time. Plans for the next day? Call me. We would figure something out.

(Start scary music here.) He leaves 5 messages on my voicemail. Not one. Not two. Not even three, but FIVE. 1, 2, 3, 4, and yup 5. Yikes! I’m listening to my messages thinking, “If I get one more message from him, I’m going to call the cops!” At this point, I don’t even want to hear or see him ever again. Psychoaggressivemaniacstalker. But that Catholic guilt sets in. I had already agreed to meet up with him. I tell him to meet me and a friend at a bar.

When he arrives, his eyes lock on me for the rest of the night. He cannot stop staring. Then the psycho starts rubbing my shoulder and arm. I’m flipping out at this point—totally at my wits end. I tell him I’m ticklish and jerk myself away, but the dumb bastard continues his Lenny-like touchy-feely gestures. Yuck!!!

What a letdown. I claim tiredness and get ready to leave. All of us pile in my car, I drop psychopath off, but before he shuts the door, my friend calls out, “Keep trying, Ray. Keep trying!” That’s right, Ray. Sail, sail away toward that beautiful sunset I had believed in just the night before. Good luck and good riddance!

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04.12.05

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Welcome to my site, derived from an advice column I wrote while getting my MBA. I live in the San Francisco Bay Area. I give helpful, opinionated advice based on my own experience and from the expertise of my extensive network. For more, click here.

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  • Blogging
  • Burning Man
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