I Went On Vacation As A First Date — Here's What Happened

Before meeting Milo, I was a casual swiper at best. Profiles on Tinder hardly piqued my interest, and the few dates I'd been on never went well. On one of these disastrous dates, I made the rookie mistake of agreeing to have dinner with the world’s most unimaginative man. Longest hour of eating orange chicken of my life. Another time, I invited a match to a hot yoga class (a workout and a date), only to realize he'd wildly misrepresented himself in his profile pictures. Right off the bat, Milo’s Tinder game was different from the rest.
Milo matched my banter and drew me in immediately. Conversation with him felt like an exhilarating game of tennis. Almost instantly, I felt like I could be fully myself, and he responded casually, wittily, and without hesitation. I told him I was sick of New York and that I wished I could move to Colombia and just fuck around. He told me he was a musician and that he'd just moved to the city. I found out he was actually close friends — and roommates — with my best friend’s ex-boyfriend. I have to be honest about how excited I was this first night. The world didn’t just feel small; it felt possible that stars had aligned.
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When Milo messaged me, "We should go hiking in Colombia sometime," I actually felt a little bummed. I thought he was blowing me off by route of making future plans that would never actually happen. Why not just ask me to get a drink…in the United States? I decided my best option was to just go with it.
"Definitely," I bluffed. "I can't do May, but June is looking good."
Milo texted back, "Anytime in June is good for me."
Seriously, that's how it went. I was suddenly going on vacation with a guy from Tinder.
Milo had to leave for a month-long work trip the day after we made our grand plan. We texted a lot but mostly discussed technical things like how to go about booking hotels and splitting fares 50/50. The first time we really got to feel each other out wasn't until we were in a cab on our way to the airport. We were into it enough to make out right then and there.
Flying, by the way, is probably the easiest way to disperse first-date tension. Between there being very little room and no way to look especially cute on a red-eye, you really can’t be worried about impressing anyone. There was a lot of throwing my arms and legs around Milo’s body in an effort to sleep comfortably on the plane.
When we finally got to our hotel in Cartagena, we immediately got in the hot tub and started making out. And then having sex. I realized it had been less than 24 hours since we'd first met up and momentarily felt disappointed in myself for not holding out for at least a full day. I excused myself, though, as I was in Colombia with my Tinder date. It’s not like he could have left the next morning and not called me.
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Afterward, we made our way to a bar with Mediterranean vibes, all tiled counters and soft-blue hues. We split a pitcher of sangria and it felt like heaven. For about a minute. Then Milo started talking about his recent, messy breakup.
"So if the relationship was so hard, then why don’t you just trust yourself to know that it ended for a reason?" I asked him.
"Because I love her."
I got it. Meeting Milo was the first time since my last breakup — just three months prior — that I’d felt enticed back into the dating world. But for Milo, this trip seemed to be magnifying the absence of the woman he loved.
This knowledge made me feel a little trapped. I was seeing so much of this man, but I didn’t know what to think of him. On the one hand, Milo was charming as hell, and we were having really fun and friendly sex. On the other, I wasn't thrilled to be on a lovers' vacation with a guy who wished he was with someone else. All I knew was that I enjoyed spending time with Milo in this tropical fantasy world we'd created for ourselves. As long as I didn't start thinking about real life waiting for us back home, he was my perfect partner in crime.
A few days in, we embarked on a four-day hike to Ciudad Perdida (The Lost City). The long days hiking were balanced with beers shared on a rock at the end of each evening. Something about exhausting ourselves physically all day made our shared love for beer and the occasional guilty cigarette feel like a seriously unique bond. In the hiker’s dormitories, we slept in bunk beds flush next to each other. Milo would always poke his head through the mosquito netting to kiss me. I forgot about being a "substitute girl."
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We spent our last night back in Cartagena. We went out to dinner but were so beat from the four days we'd spent hiking that we hardly made conversation. Mid-meal he asked if I wanted to go out afterwards...
I froze. "Go out after this trip? No, no I don’t want to do that," I said, to my own surprise.
"What? I meant after dinner."
"Oh! Oh, I don’t know," I almost whispered.
"We don’t have to talk about going out after this trip. We really don’t," Milo said.
"Well, though, I’ve been thinking about it. It’s our last night, and I don’t know. I just feel like you’re so complicated, I couldn’t actually date you."
"I’m really not in a place to date right now," he said flatly.
"Right."
"What happens in Colombia stays in Colombia," he said, and flashed me a reassuring smile.
It’s been a month since I last saw Milo. We shared a taxi from the airport and split ways. Back in New York, just like that.
The serendipitous, spontaneous romance I'd wanted from our trip was blotted out by the reality of our flaws and the situations in our lives, much like what happens in any failed relationship. Real life got the best of us, but it couldn’t have us in Colombia.
My brief relationship with Milo forced me to face my own relationship hangups. Seeing Milo's intense sadness over his ex made me wonder if somewhere along the way I had lost the ability to care for someone that much. To be so fully immersed, even, in the events of my life. Though he was visibly hurting, I admired the intensity of his feelings. In a way, he’s inspired me to allow myself to fall that freely — without guardrail or caution — in love one day, too.
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Here is what I’ve ultimately brought home with me: I might not get to keep Milo romantically in my real New York City life — certainly not in the carefree way that I was able to on our travels. And I’ve missed him often since we’ve been back. But I would do it all over just to find myself lying on a rock in the middle of a rushing river, in a vast jungle, in a foreign land, with a cute boy who reaches over to kiss me. Maybe that moment is enough of a reason to take a romantic leap every once in a while.
Find more dating and relationship drama on season 1 of Relationship Status, available on go90.
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