A Night Out With Dad

By Josh Cain * Other Josh Cain Posts

I was pretty sure my friend Gabe was about to be disappointed. It was his first time in New York City and I had just found a bar that would let 18 year olds drink. For some reason his enthusiasm was undiminished by the facts that a) it was a Tuesday b) we were being allowed to drink because the bar was almost empty and my dad knew the owner and c) the only reason the bar was “almost” empty was because my dad was the sole patron.

We arrived to find a simple bar adorned with various sporting memorabilia and outfitted with a dozen televisions, each displaying groups of men using some combination of sticks and/or balls to make scores and thus earn the adulation of the unwashed masses. At the bar sat my father, a handsome 50-something in t-shirt, jeans and a baseball cap casually drinking a beer and watching the progress of his favored squadron. It may seem weird to refer to one's own father as “handsome,” but he once went to a pornstar convention and had to pretend he was gay to keep from getting jumped by the women there. I’m not even joking. The best I’ve managed to pull off is having an overweight drunk girl talk to me at a frat party before pausing to vomit on herself.

Hanging out with Dad was the staff: the bartender, a pudgy, jovial guy who was clearly in his element talking loudly and drinking beer while watching sports; the waitress, a tall blond who might have been hot but looked like she’d lived hard; and the owner, a cute little blond bouncing with energy who was clearly slammin’ back in the day but whose hotness was diminished by the fact that she was at least 40 (which might as well be 80 to an 18 year old).

Gabe and I joined my dad and grabbed beers, made all the more delicious by their illegality. I quietly sipped while Gabe and my dad discussed athletics and politics, two subjects where I know nothing and have no interest in learning. It was likely due to this distraction that I overheard the owner proudly describing her custom-made underwear that prominently featured her own face on the crotch. When the bartender heard this he exclaimed, “oh yeah, check this out! Thunderbolts!” slightly pulling down his pants to reveal the electric undergarments in question. I am, of course, an asshole and thus feel the need to one-up people whenever possible (that’s pretty good, but I’ve got a way better public urination story), so I foolishly said, “man, I’ve got cooler underwear than that.”

Conversation halted and everyone froze. After a few seconds of silence the owner issued a challenge, “Let’s see ‘em,” she whispered.

“Uhhh…I’m not actually wearing them right now,” I said. The superior underpants I had in mind, namely Spider-man undies and my Monopoly board boxers with “Water Works” over the fly, were both items I saved for special occasions. 

“I said show me your underwear,” she said more forcefully, the waitress and bartender shouting down my protests. “Get behind the bar and drop trow,” she ordered.

Uncertain and grasping for help I turned to my father for assistance. Our eyes met and with a slight nod he said, “Do it, son.” This might seem like an odd reaction for a parent, but when you view the situation as a man who once complained that there were just ten truly gorgeous women at his college and he “only” dated 3 of them speaking to his 18 year old virgin going on 19 year old virgin son, you can maybe understand why he was encouraging me to take my pants off in front of women.  

With a resigned sigh I hopped over the bar and soon found myself wearing distinctly uninteresting grey boxer briefs and holding a bottle of whiskey. Gabe’s laughter at my predicament was quickly silenced as the increasingly excited owner commanded him to join me in my state of undress. Pantsless and confused we were told to create a drink neither of us had heard of. Gabe and I floundered behind the bar amidst the cheers of my father and the staff. This was accompanied by the occasional comment by the waitress indicating that she thought we were both “cute,” but “preferred darker men,” leering at me as she said this. The surreal nature of putting on a sex show for two older women and my father allowed me to dissociate myself enough to focus on the task at hand and eventually slop some random combination of liquors into several shot glasses.

We took our shots with gusto and the owner announced that we were going to get our “reward.” As she leaned over the bar and grabbed the bottom of her shirt, the bartender started hitting me on the shoulder and saying “oh man, you are so lucky!” As I turned to face him to figure out what about this event could be construed as “lucky,” I heard a collective cheer. As I turned back with a puzzled expression Gabe leaned over and informed me that we had just been flashed. Yet again I had been denied the adolescent Holy Grail that is the booby.

As I rejoined my dad, newly pants-wearing, he took me aside.

“So I was talking to that waitress,” he said, “and she offered to take you home and show you some things if you’re interested.”

Slightly aghast, I asked, “How old is she? Like 26?”

“38!” he said brightly, a smile creeping across his face.

I admit that I did consider it, but decided that I didn’t want my first time to be associated with public degradation, a woman twice my age, and having my father as a wingman.

“I’ll pass,” I said to him. He told me that it was ok and, strangely, didn’t seem disappointed.