“Stop flirting with me or kiss me.” So I did.
The summer after high school, my older brother’s friend got me a job barbacking at a small club – normal, relatively quiet, bar five nights a week, packed hip-hop club on the weekends. It was a great gig – cash under the table, minimal hours for enough money to have fun, a sharp increase in alcohol tolerance…
I was young and enjoyed the job, so I worked hard and quickly became the owner’s personal barback in the DJ room on weekends. She could count on me to keep everything stocked and glassware clean, which earned me a number of free shots and lessons in bartending.
We had a rapport but I didn’t think much of it – Alyssa was in her mid 30s, married, a couple of kids, not smoking hot but very cute. I had dated but nothing serious and I was pretty self-conscious about being a virgin. As a young, six-foot tall white guy with red hair to my shoulders I got a lot of attention from the mostly black female clientele but I had no game and never could figure out how to proceed. All summer the best I could do was an occasional makeout session.