One of life’s most valuable lessons is to never assume. I learned this a few winters ago while living in Chicago. A couple lady friends were in town for the weekend to explore the city’s nightlife. They invited me to come out with them, so I accepted. I was on my own that night. My roommate had a severe case of the itis so he was on the couch passed out farting in his sleep pretty early. I took the train downtown and met up with the ladies. We club hopped, and as the evening carried on and the drinks flowed, the flirting increased exponentially between me and one of the ladies. We stopped by one of Wicker Park’s 4AM bars after all the 2AM clubs downtown closed. We were hugged up ever so tightly. We were drunk in love in that moment and it was glorious. A street artist even stopped us and drew a picture of her for $1 and told me I was a lucky man. The picture was terribly drawn, and in crayon, but it was a nice gesture and only $1. Her friend made some new friends at the bar and eventually disappeared over the horizon with a couple of random black dudes. It was time to call it a night. My lady and I took a cab back to the hotel she was staying at. I was almost to the promised land. We entered her room at about 4:48AM, and she went to turn on some mood music on her MacBook. By the time she turned around, I was laying on the bed butt ass naked. She was startled. “Damn you got naked fast. We can’t do all that tonight,” she explained. “Oh,” I answered with a slight quiver in my lip. I knew exactly what she meant, and neither of us wanted to wake up laying in a crime scene. She sat at the edge of the bed as I searched the room for my Hanes briefs that I recklessly threw somewhere in the room upon removal. I couldn’t find them in the darkness, so I had to put my jeans back on with no draws. There was so much friction in the room and in the confines of my trousers. We spooned until she fell asleep. I had real tears in my eyes… Not because of the sadness I was feeling, but from the pain of sleeping in jeans with no draws on while spooning with a curvaceous woman. I woke up a few hours later, still quite drunk, but I had to get back to campus for class. I kissed her forehead to avoid a mouth full of morning breath, and exited the room smoothly. However, I completely forgot to grab my missing draws, and had to take the Red Line train, mid-winter, back to campus with no draws on. It was an indescribable discomfort. The brutal Chicago wind found it’s way all up and through my Levi’s and other restricted areas. It was one of the darkest days of my life. I never saw those draws again. Never assume.