When He Starts Drawing Diagrams on a Napkin, It’s A Good Time to Leave

Part I
About 15 years ago I made my maiden voyage to Martha’s Vineyard. I was meeting some friends who lived in LA and knew the Vineyard really well (WASPS opening their world to a Jew who wasn’t used to crossing water for the weekend.)

I ended up on a small, rough-hewn ferry, not like the ones I’ve been on since with their wireless and wine. There weren’t many people on the boat, just a handful of us, so the handsome, pock-marked man with a calm look caught my attention. I don’t remember how we ended up talking (my ex-husband would say that I probably pushed my breasts out and tossed my hair, something he always says I do when I flirt)but I found out that he was the roadie/manager for a band that was playing at a bar in Oak Bluffs very close to where the ferry docks. Somehow I wormed my way into his lunch with the band members at the bar. I probably drank my signature drink from back in those days–a white wine spritzer– which probably got me tipsy after only one (I’m still very much a light-weight–I now stop after two glasses of non-spritzy wine.)

I can’t remember if (let’s call him….”Clive”) Clive was paying any attention to me but I was comfortable enough to hold my own. After lunch, I walked to my small hotel, very “London bedsit,” and probably the only place under $150 a night on the Vineyard. The guys from the band asked me to come see them play that night and I didn’t think that there would be any way in hell that my two gay, West Coast friends would come with me to continue my flirtation with a roadie for some hippie-ish bar band. But, well, they did and it actually became their MISSION to get me laid by a roadie for some hippie-ish bar band.

My friends and I had a great time at the bar and the band was surprisingly excellent. When they had played their last set and Clive started breaking down, my friends URGED me to suggest that he come back to my hotel room. Even NOW, in my recently-discovered sexual confidence I couldn’t see myself being quite that bold, and back then? Unheard of. The bar lights were flashing last call, and my friend was insisting that I slip him my room number. Somehow, it ended up on a napkin along with my lipsticked mouth imprint and my friend ran to the stage to give it to him. I was mortified. I was thrilled.

Like a ship captain’s wife holding vigil, but without the widow’s walk and flowy white nightgown I always picture the pacing widows in, I stared out my window almost all night, waiting for Clive to walk up the path to the hotel and come rap at my door. I TRULY believed that it would happen and it would be the beginning of a whole new kind of me. The bed was right under the window and I remember just finally sinking, rather sadly, into sleep. When I left the next morning to go meet my friends, I noticed that they had left a little note taped to a post that said “Gayle’s Room” with an arrow pointing in my direction.

(A detail that I can’t remember now, but is so typically me): The internet was in its infancy stages but somehow, I found out Clive’s home address. He must have told me where he lived (New Jersey? Connecticut?)I found a postcard with a Vineyard sunset and said something about how I was disappointed that he never made it and mailed it off. After that, I ended up at my first nude beach where I had it in me to go topless, and probably like every human being who has ever been there, saw Alan Dershowitz, naked except for a straw hat, strolling along the sand.

Part II

Back in Boston, resumption of real life. The Vineyard always seems so NOT real. Again, details fuzzy, e-mail primitive, but somehow I found yet another way to contact Clive and I received an e-mail back, with some semi-apology about not coming back to the hotel, how he had taken a late-night walk and watched the sunrise. At the end of the e-mail, though, he said that there was something he really wanted to talk to me about in person and wondered if I would meet him in Providence when the band was playing, sometime during that next week. Something he needed to talk to me about in PERSON? Was he going to profess his love for me and needed me in front of him to kiss passionately and carry me away into the Providence sunset? In my mind, that was the only option and I told him that, yes of course, I’d be there.

On the night in question, I had a work barbeque at a board members fancy house. I remember that it was HOT and I was having serious hair worries (this was well before flatirons were available to the masses, when now, every day can be a good hair day.) A few people there knew that I was going straight from there to a “date” and were all very excited for me. I drove the hour-plus thinking of nothing else but how exciting a first kiss would be.

I walked into the rather large place and saw Clive, in shorts, Timberlands and a tee-shirt. We hugged each other and sat down at a high-top table, ordered drinks, some pub-ish food and made quick small talk. Within maybe 8 minutes, Clive pulled a napkin out of the dispenser and took out a pen.

“This is what I wanted to talk to you about.” He started drawing boxes and arrows and began to describe something that I couldn’t even follow. Why was this man DRAWING DIAGRAMS ON A NAPKIN WHEN HE WAS SUPPOSED TO BE KISSING ME????? It didn’t take long before the boxes became a pyramid and I realized what was happening. I became an arrow on the bottom of a pyramid. He thought that I would bring him money and a bump up to the next level. To this day, I’m still confused how “boxes” could make someone rich.

I let him finish his spiel and he went back to setting-up for the band. I was stunned. I was temporarily immobilized. I had an hour and a half drive home and it was already way past my bedtime. All I could think about was how it wouldn’t matter anymore if I smoked a million cigarettes because my breath wasn’t an issue. I’m pretty certain that I had it in me to laugh, shake my head and not blame it on myself for being deficient in any way.

There have been some other doozies of dates and situations since then, but, I’m sure that this will stand out as one for the “Dates From Hell” record books.



  1. That's my uncle Jackie! Swear to God!

  2. Dan

    First: "Alan Dershowitz naked, except for a straw hat" made me throw up in my mouth a little bit.Second: We do NOT bring these things upon ourselves. By saying "yes" to life, you sometimes set yourself up for these little, um, "moments," but it beats saying "no." Keep writing, Gayle. This is good stuff!

  3. Seems I picked a good story for my first read of your blog. I'm hooked and can't wait to delve into more. I'm excited – for me and YOU!

  4. Egads. I had a somewhat similar experience with an old friend from college getting in touch after ten years, calling and chatting for over an hour about our marriages and our kids, and then him calling a few days later and leaving a message because he "forgot to ask me something", and when I called back, got a similar spiel. I felt dirty, I talked to him about my CHILD, and have not talked to him since. Creeps.

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