Like most men before getting hitched, I snatched defeat from the jaws of victory plenty of times, but few fails rival what transpired in 2006 when my friend Scot and I visited South Beach. I had arrived first and met two women visiting from Uruguay, and they agreed to meet us for drinks later that night at the Clevelander. The sharply dressed Uruguayan ladies arrived at the Art Deco bar shortly after we did.
“So, where are you from?” asked Scot, a bulky Chicago native with a tough-guy tone.
“From Uruguay,” said the first woman. “Do you know where that is?”
The correct answer should always be, “Yes, I hear it is a wonderful place.” That was not my friend’s response.
“No,” he said. “I don’t know any of the countries down in South Africa.”
“Ha! He’s kidding,” I stammered, my chuckle as unconvincing as a low-budget telenovela.
“Huh?” replied Scot, bemused.
The women exchanged a split-second glance before one of them remarked, “Actually, we stopped by to say we are not able to hang out tonight, but thank you for the invite.”
“No problem,” I said. As the ladies darted for Ocean Drive, I glared at Scott and said, “South Africa isn’t even a continent!”
“What you gonna do?” replied Scot with a nonchalant shrug.
With this exchange burnt into my frontal lobes, a call I received a month later almost seemed surreal.
“Hey Dave, you ever been to Uruguay?” asked my friend Eric. “Punta del Este is like the South American riviera, and I am going for New Year’s Eve. Are you interested?”
The Portlandia-raised Angeleno wanted a wingman who knew Chile from Chad, and I agreed to go, but the experience would show I apparently can’t tell Chloe from Chad. But we’ll get to that later.
Ibiza-style Punta del Este sits on a peninsula, but the Punta reference typically entails a stretch of coastline that extends 20 miles northeast past La Barra to Jose Ignacio, the poshest of the beachfront towns. The famed Bikini Beach sits on the outskirts of La Barra, and Lonely Planet said you must “tan it, wax it, buff it” before daring to step upon its fine sand. In decades past, this coastal strip reportedly hosted the likes of Che Guevara, Brigitte Bardot and the Rat Pack, and its current celebrity clientele led the travel press to dub Punta the St. Tropez of South America.
“If you want to get wild on the beach, the place to come is Punta del Este,” said host Natalia Cigliuti in a 2001 episode of Wild On E! filmed at Bikini Beach. Five years later, Punta had only become more festive, and New Year’s Eve in the middle of summer is the peak of high season.
After arriving in the capital city, Montevideo, we had to take a bus to Punta del Este. I sat next to a woman who also came down from Los Angeles for New Year’s Eve. “I won’t go to a nightclub unless we have a table and bottle service,” she said, as the beat-up bus rolled down the highway. The woman had spent New Year’s Eve here several times before, and she told me about the exclusive villa parties and luxury night clubs. Eric and I looked like thirtysomething backpackers who didn’t know the meaning of bottle service, so obviously no villa party invites were forthcoming.
Jetlagged and exhausted, we arrived in La Barra and quickly headed out for a drink at one of the waterfront bars. The beach, with DJs spinning dance music on the sand, was packed yet still manageable. As is often the case, the first day after a long flight is more low key, and we spent most of our time jumping from bar to bar. Day two, however, meant hitting the beaches and enjoying the South Atlantic, but what happened that morning is still very much up for debate.
“You got stung by a jellyfish, and you kept asking me to pee on you,” Eric claimed in a recent conversation about the trip. “You were mad that I wouldn’t do it.”
“That never happened,” I retorted. “That is not something I would forget.”
“I swear. No joke.”
“Look, if it did happen,” I rationalized, “I would have found a bathroom and urinated on myself before asking a friend to do it. I wouldn’t risk that type of ridicule.”
“Maybe you got stung some place where you couldn’t piss on yourself,” he countered.
“Like on my back?” I said. “I would have emptied a beer can, pissed in it and then poured it on my back. I certainly wouldn’t get on all fours and ask you to urinate all over me.”
“I’m just telling you what happened,” he said. “You wanted me to pee on you.”
While I am certain I never asked Eric to make it rain, the party that night involved a situation I cannot deny. We spent the night in downtown Punta visiting the casino and drinking at popular bars like Tequilas. In between watering holes, we saw a group of women by the harbor. I walked up to the most beautiful woman in the group and introduced myself. She smiled and flirted and told me they were visiting from Brazil.
“I really like you,” she said without a demoralizing “but…”
“I like you, too,” I replied with an air of cockiness.
“That is why I want to be honest with you,” she returned. “I was born a man.”
Apparently my year living in West Hollywood did little for my deduction skills.
“I would have never guessed,” I replied as the beer goggles abruptly fell from my face.
“That is what I thought,” she said with a smile.
We exchanged a few friendly words, and I rejoined Eric. He looked surprised. “What are you doing? She’s hot, and I think she likes you,” Eric said, per my crystal-clear recollection. He denies saying this, claiming all he saw was me running for a taxi “visibly shaken.”
Night three: New Year’s Eve. After spending the day at Bikini Beach, we broke out our button-down shirts and headed back downtown. That’s when Eric dropped a surprise question.
“You want to do ecstasy? I brought some with me from the States,” he said.
Uruguay is now cannabis country, and if it were Thanksgiving, a sweet sativa would be perfect, but MDMA and alcohol made more sense for New Year’s Eve. We both popped a pill and spent the next six hours walking the boardwalk and drinking at Moby Dick’s bar near the harbor. I even attempted to dance, though not even the MDMA could improve my Ewok-y dance moves. Right before midnight, we headed to the beach for the fireworks, but overall, the night was relatively event free. We crashed out sometime around two in the morning and flew home the next day.
On the surface, the trip seemed like another face-flop in the romance department, but it was actually what the religious folk might call planting a seed on good soil. Remember the “table and bottle service” woman from the bus? She transformed into a backpacking road warrior visiting 100+ countries, and we randomly reconnected three years later and spent several months traveling South America. During a stop in Medellin, Colombia, she made friends with a group visiting from Bogotá, and in that group was the woman I would marry.
My future wife and I exchanged information after pounding aguardiente shots at a debaucherous, sexist and politically incorrect Medellin nightclub that claims to have “the largest staple of midget performers in South America.” But we’ll save that story for the next _de_Generation X.
Photo: Juan José Richards Echeverría, CC-BY
David Jenison is a Los Angeles native and the Content Editor of PROHBTD. He has covered entertainment, restaurants and travel for more than 20 years.