My Picture-Perfect Holiday Fling Was A Beautiful Letdown

Dreaming of a sun-kissed holiday romance? Our editor reveals the strange disappointment of getting everything you thought you wanted…

Every winter, Hong Kong enters its year-end holiday ritual: the typhoon rains dry up, cold winds blow in and a city of underpaid 20-somethings frantically seek discount flights to anywhere warmer. By mid-November, my inbox was flooded with HK Express deals to Bali and Phu Quoc, promising paradise for less than a week’s rent. But I always closed the tab before booking, resigned to another grey winter.

Then came the Instagram notification. Gabriel, an older friend I hadn’t spoken to in years, replied to my story, asking about my holiday plans. When I told him I’d be in his hemisphere soon enough (visiting relatives in New York) he told me to stop by San Juan. “Stay for a week at my family’s house,” he offered in his characteristically quippy tone. “You don’t know a good time until you’ve been to Puerto Rico.”

At first, I hesitated. A week with someone I barely knew anymore — plus his family? It felt absurd. But then I considered the white sandy beaches, Gabriel’s lopsided smile and all the bad vacation rom-coms I’d ever seen: the kind where that sort-of friend, sort-of stranger turns out to be The One. This time, I decided, I wouldn’t overthink it. No more saying no to the universe. Minutes later, I booked my flight.

Fast forward two weeks, and I was sliding into the front seat of Gabriel’s car outside Luis Muñoz Marín International Airport. I braced myself for awkwardness, but the drive back to his house felt surprisingly familiar. We talked about his business in Taipei, how I still wanted to write for a living, and how much time had passed since we last saw each other. At one point, he reached over the dashboard, caught a strand of my hair between his fingers, and observed that it was longer now. “In a good way,” he laughed.

It was a simple gesture, but our eyes met for a moment as he returned his hand to the steering wheel, and suddenly it was clear: We’re going to sleep together. It felt inevitable in a way it hadn’t before, when we were friends in ‘real life’ and our five-year age gap felt more stark. Now, looking out his car window, tropical air washing away my typical neurosis, I got the strange impression that my teenage crush was belatedly reciprocated.

By 1am, we finally arrived. Gabriel carried my bag upstairs and showed me the guest room, interspersing quiet commentary: “You can use this towel,” and “Don’t drink the tap water.” Then he said goodnight, and suddenly I was alone. I’m at Gabriel’s house in Puerto Rico, I thought, but it still didn’t feel real. As I drifted to sleep, my mind flashed back to the late nights I’d spent in his apartment in Hong Kong, wishing just once he’d ask me to stay.

The next morning, we went straight to the beach. Gabriel’s best friend was waiting outside and, seeing me, let out a sputtered laugh. As we filed into the car, he said something loudly in Spanish that provoked Gabriel to cuss him out. “Sorry, J doesn’t have my manners,” Gabriel said quickly. When I reminded him I don’t speak Spanish, they exchanged a look, and for the rest of the ride neither spoke any English at all.

The beach did not disappoint. I felt like I had stepped into a postcard — clear blue water with white foamy tips, lines of palm trees and brightly coloured towels scattered across the soft sand. We found a patch of shade, put down our bags and stripped down to our swimwear. J unearthed a six-pack of Medella Light and offered a bottle to me and Gabriel. I refused, pointing to the water. “I’m going to swim first,” I told them. Gabriel got up immediately; J laid back, opened his beer with his teeth and mumbled something in Spanish.

So off Gabriel and I went, walking, then running, into the waves, which crashed around and swelled us further from the shore. It was blue as far as the eye could see. No longer able to stand, I floated on my back in the cool water, feeling like everything in my life had led up to this picture-perfect moment.

“Paradise, right?” Gabriel teased, swimming nearer to me. I wanted to reply with something witty, but got distracted by his proximity — he was so close now that I could feel warmth radiating off his body. Cue the love song, I thought to myself as he leaned in. And then we were kissing; softly at first, then deeply, his arms holing me steady in the waves.

Of course, I’d already rehearsed this scenario on the flight over. My friends teased me mercilessly before I left, saying there was no way we’d remain platonic. I’d laughed it off, but here we were, making out on a perfect beach under the perfect sun on a perfect day. My very own movie moment, replayed a thousand times in my head and now being lived. And yet, the magic feeling I had imagined wasn’t there.

You should be, like, ecstatic right now, I told myself as we swam back to shore, this is literally why you came. But something felt off. It was almost too easy, all of this. I had anticipated more buildup, I guess, or maybe it was our old dynamic that I missed. I wondered, am I so cliché that I only liked Gabriel because he didn’t want me back?

The sun had set by the time we packed our bags and returned to the car. Gabriel and J had another unintelligible Spanish conversation as we drove back, which ended with Gabriel pulling over at a bus stop and J getting out. He said goodbye comically slowly, dapping up Gabriel and winking at me before closing the door. It was clear where the night was headed. The thought didn’t exactly titillate, but who was I to protest fate?

From that moment, everything played out predictably, albeit on 2x speed — radio blasting on the drive home, a quick dinner and a bizarrely silent smoke on his porch. I could sense him working out how to initiate so assiduously that our typical banter seized into strained politeness. In the end, he landed on the wonderfully original: “Want to see my room?”

The sex was over as soon as it began. Gabriel sweatily collapsed onto the bed, his arm slinging over me in an uncomfortable half-hug. “Wow,” he said into my hair, his breath hot. I stared up at the ceiling fan and watched it turn for several weighted seconds, then mustered up an unenthusiastic “yeah.” This is why you don’t fuck your friends, I thought before wriggling out from under him and pulling on my clothes.

Gabriel, who I had always known as all-charm, seemed deflated by my lack of post-sex adoration. He coughed awkwardly, redressed and began to relay our plans for the rest of the night — dancing with some friends, maybe a late night snack. “The clubs here are the best, seriously, there’s this DJ…” he went on and on.

I wondered, am I the worst person in the world? Here I was, staying for free in this beautiful city, with an old friend acting as chauffeur and tour guide. He organised itineraries for every day I was there; planned to introduce me to all his friends; wasn’t letting me pay for anything. All I had to do was pretend to enjoy sleeping with him. Even this I couldn’t manage. It wasn’t supposed to feel like this, I thought.

The truth was, I had underestimated the delusion that predicated my holiday fantasy. I just want to lie on a beach, I told myself. “Plus, I might end up falling in love and having the best week of my life” was the unspoken second clause. But I had successfully convinced myself that, in this foreign land, I would emerge as A Very Chill Girl — one who totally never projects fantasies and expectations onto unwitting friends.

Was it so bad that I wanted to escape my routine and responsibilities, at least for a brief tropical moment? No, I suppose we all do. But as the weather cools and the sun creepingly begins to set earlier, I remind myself that my dream life isn’t waiting underneath a palm tree on the other side of the horizon, Medella in hand.

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