My First Affair with "Miss Amy Wineglass"

Part Two

The Moon Man Chronicles
The Scarlett Letter
5 min readDec 28, 2021

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Photo by seabass creatives on Unsplash

As soon as I realized who it was standing on the black asphalt a few feet below me, I immediately regretted my decision not to pack more t-shirts.

Typically on a 3-stop weekend run, you would only carry what you could pack into your backpack and whatever instrument you needed. In a flash, after Amy introduced herself, my brain was retelling me the story of how I got to this place.

Running off stage, hand slapping with some of the crew, someone handed me a blue Gatorade, which I promptly drank half, and I grabbed my towel to wipe down. Sadly, I was down to my last shirt, which I placed on the bench next to the half-filled blue Gatorade. The same bench that one of my intoxicated bandmates decided to use as a placeholder for a woman so he could show us all how he intended to "bang this broad silly." During this desperate attempt at masculinity, which always fails, the only ones who suffered were my eyes and my last clean t-shirt.

Only one person in the crew had a clean shirt that fit me, and she was married to the bass player. Maxine, or affectionately called Max, was essentially the "Band Mom." She looked after us all while we were on the road and on-stage. Whether we asked her to or not. Max was about 5'9, weighed about 230lbs, and was completely obsessed with only two things in this world. The Bass Player and the New Kids on the Block.

And since we didn't have any t-shirts, I was wearing a New Kids On The Block Tour T-Shirt.

Smiling and ready for a self-deprecating introduction, I placed both hands on the ground to push myself off the dock. "Amy, nice to meet you; I'm Moon, and let me state for the record, I am not a New Kids fan at all. Although Donnie Wahlberg is dope as fuck on that cop show but other than that, this isn't even mine…".

I could tell she tried to think of a better comeback, but she also knew the value of a well-timed response. "You're not? Well, then this whole thing is a waste of both of our time. Are you going to light that thing or what?" she responded with a slight grin as we stood face to face for the first time.

Standing on a stage and looking down, it's always challenging to get a read on how tall someone is. However, even in her flip-flops, Amy was only about 3 inches below my 6'1 height and curvier than I had thought.

"Yeah, yeah, hold up.." I stuttered as I reached back up on top of the deck to grab that still very large joint I had put out before. "Amy, you scared the shit out of me coming through the vans with all those questions. I thought you were the Manager Lady coming out here to kick my ass." Amy's eyebrows raised in an amused arch at my statement while I lighted the joint for the second time.

"That Manager Lady is my Aunt, and she wouldn't kick your ass," she responded while reaching for the already lit joint. "She'd probably kick my ass for being back here with you." As she placed it between the two lips that I had been staring at most of the night, I had transformed into a grade school kid and foolishly thought, "Did we just kiss?."

"What did I do? I was sitting there. We saw each other earlier. You came over here. Seduced me into giving you my weed." I said with a sarcastic smirk. I was feeling the effects of way too many hits now and getting a little more confidence with every heartbeat. "Trust me, Moon," she paused to take another pull and held it in her lungs while she spoke,

"If I seduced you, you'd be giving me a lot more than your weed."

Photo by Gijs Coolen on Unsplash

Standing there, in between two tour vans, holding myself up with my left hand on the truck behind me, I remembered what it was to feel flirted with in person. On-stage, when a musician is flirting, especially a married one, there's a pretty good chance they're doing it for the job. You may find a few women in the crowd that is sending you some vibes, and you may decide that those women will feel sexy tonight. You may never talk to them, you may never touch them, or even thank them for their unending support, but they'll forever be a fan of you.

I decided it was time to address the elephant in the room at that point. My left hand held something on one of its digits that I noticed was not on Amy's. A Wedding Ring. "You do realize I'm married, right?" I asked with no ulterior motive other than to restate the obvious. Maybe not to her. Maybe to myself.

As she passed back the now almost burned through joint, she looked up once our fingers had touched and successfully passed it. "I do realize you're married. I am too. I also realize that we haven't broken any vows either." she said back to me in a reflective tone.

I crushed the last remnants of our shared experience underneath my Nike AirMax and returned the lighter to my jeans pocket. As I brought my head up, it was Amy who had suddenly latched onto me and brought both of her arms up to my shoulders. She locked her fingers around my neck and leaned her body against mine. The force of which pushed my back against the side of the truck where I just had my hand.

Reaching around her waist with my right arm, I steadied us both and looked deep into those same eyes that had bewildered me all those months back. Holding silence for what felt like hours, she smiled and put her head on my chest.

Breathing deeply for a second, Amy looked back up, kissed me on the lips, and said, "This is nice. We should do this again. When are you coming back here?" I didn't know and didn't have my phone to check, so I answered, "A few weeks, I guess. Will I see you, or will you be playing with that bar napkin on the wine glass again?" Confused and interested, she looked up and said;

"What napkin on a wine glass?"

Part 3 Soon

Moon Man

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The Moon Man Chronicles
The Scarlett Letter

I write pieces about the human condition, things that I like, and stories about the debaucheries of my life. simplemanonthemoon@gmail.com