03/17/2015 01:50 pm ET Updated May 17, 2015

The Questionable Success of My 21st Birthday

Good News: An all‐paid vacation to Key West for my 21st birthday.

Bad News: An all‐paid vacation to Key West for my 21st birthday with my non­‐alcohol­-consuming mother, father and older sister.

It seems I spent my lifetime waiting for my 21st birthday: those 24 hours where by
American standards I am supposed to be a staggering drunk with my best buddies, testing the limits to see if I survive to the next day.

I put on an air of excitement when my parents surprised me with a trip to Key West to celebrate. In reality, the thought of taking shots with my mom wasn't quite as enticing as a night out in my college town with friends. I worked very hard though to persuade myself that participating in such revelry with the family might not be so bad. Granted, I had spent a lot of time convincing myself that my 60-­something­‐year­‐old lawyer parents were up to the task of giving me a memorable 21st birthday.

As the day approached, I was conflicted: do I attempt a night that would make my fraternity bros proud? Or do I cross the portal to adulthood like a civilized, mature adult?

The reality of my familial situation convinced me that the quiet (boring and sober) approach was the only real option.

I went to bed at 10pm on the eve of my big 2-­1, shutting down my fantasies about the ritual bar crawl that surely would have ensued back on my college campus promptly at 11:59 PM. I arose the next morning with a big, pasted-on smile, attempting to show my parents there was no other place I'd rather be.

We started the day with an educational trip to the Ernest Hemmingway home. The tour guide's numerous anecdotes, however, of Hemmingway's incessant partying were a harsh reminder to the pitiful start to my day.

Later, all four of us lumbered around town and lounged by our hotel pool. In short, it was a day the average American 21-­year­‐old would absolutely deplore.

At dinner, my inner partier peaked its head out. I suggested we should try out the bar scene tonight - you know, we might as well make sure my shiny new ID works and all.

Both my parents pulled out their thoroughly underlined Key West travel guides and started reading aloud the various options.

From the moment they booked our Key West tickets, my parents said to me, "It's so gay down there - you'll love it." Sure enough, they were right. We passed by bars with towering drag queens in six‐inch stilettos with names like Madame Ovary and Misty Cologne, recruiting passers‐by into their raucous world.

We ended up at an open­‐window bar with a half dozen men gyrating on the bar counter, dollar bills hanging from the crotches of their thongs. What a sight to behold, my flesh and blood relatives and me, watching Adonis males playing peek­‐a­‐boo, sliding their thongs up and down to give titillating looks of their bare butts and the promise of more, to the appreciative cheers of the mostly gay crowd.

"Is this gay enough for you?" my dad asked, Diet Coke in hand and twisted grin on face. Yes, my dad, standing there clad in his Lands' End best, obviously pleased with this daring departure from his uptight comfort zone.

Without waiting for my answer (which even now I don't know how I would have possibly responded), my parents and sister were already dancing along.

"Oh, how fun!" Mom exclaimed.

"Do you think they're straight?" my sister asked with more hope than confusion.

"I want a body like that!" my dad shouted, choking on his envy at the toned bodies-­in-­motion.

The bar was sweltering hot and the Christina Aguilera playing in the background was
deafening (while at the same time utterly fabulous).

The perfectly toned dancers flocked to us - the wholesome, Midwestern family with
their capris, Crocs and wind breakers. They crowded around us, their junk flying in every which direction, my parents cheering and the dancing boys clearly very confused about my family's dynamic (and sanity). I was the only member of my family without a dollar waving in the air.

Of course, being the talkative Jewish mother that she is, my mom ended up having a "wonderful" conversation with the bartender, while my dad pulled out his notepad and began asking the hunkiest of the dancers his workout and diet routine.

After they seemingly were satisfied with their stud fix, we left the bar, all of us wretchedly and utterly sober.

As it turns out though, my parents were just getting started. In my dad's efforts to be ultra hip, he read in his tour book about a "fun, clothing optional bar" just down the street. They started walking in that direction and I had no other option but to follow. I was admittedly very interested to see what a clothing optional bar would actually be like. We walked up three iron­‐wrought staircases and entered an outdoor garden­‐type bar scene, the lighting muted.

So there we were, the four of us goonishly standing in the corner, taking in all the patrons, hoping to be the first to spot a shirt coming off. At this point in the night though, I was just worried that my mom or sister - or even my dad - would be the first to disrobe. The beefy bartender explained that clothes don't come off until later, with some alcohol­‐fueled inspiration.

My sister, while we were back on noisy, neon Duval Street, then noticed the big "Coyote Ugly" sign, just like the Tyra Banks movie where sexy women danced atop the bar. My family ran in. There was no stopping them now.

Apparently, "Coyote Ugly" was more apt a name than I ever could have imagined. We sat at the bar in complete horror as girls "danced" around us. One woman wore her glasses and another even dared to wear red spandex under her jean shorts. Honestly, I saw more seductive moves at my seventh grade Bar Mitzvah party.

I immediately encouraged our hasty exit when I began to sense my mother and sister contemplating a step onto the bar, despite their 0.0 alcohol contents. I reminded them of their surprisingly forgotten suburban sensibilities.

We tore down the streets of Key West in our rented red Mustang convertible, a family on the run, back to our hotel. I was in a state of wonder. What would have transpired had this mature 21­‐year-­old not been there to supervise?

Now, as I reflect upon a night I surely won't forget, I pose the question: did I fail my 21st birthday? Or did I possibly just have the ultimate night with the coolest, most badass parents?

You decide.