The First Time I: Hooked Up with Someone I Met on Vacation

This is The First Time, a column where Zach either 1) writes about the first time he did something specific in his life and talks about any pop culture connections surrounding it, or 2) tries something for the first time ever in 2025 and writes about it—sees a new movie, eats a new food, etc. etc. etc.

I have gotten so much from Gloria's stories from her life that she has included on the blog. One after another, they are incredible. Her story about not hooking up with Brent only reinforces that. Friending someone on Facebook after rejecting their move? How lukewarm. And, yet, I'm sure I've done things like that before.

So it's Gloria who inspired this post. I have hooked up with someone I met on vacation. It wasn't a meet cute in the way Gloria described in her story, but I certainly did meet her on a trip far away from home.

As a kid, my grandparents on my mom's side would sometimes take all their kids and grandchildren to St. Croix during Christmas vacations—they owned property there. It's probably the most bougie thing I've been a part of in my life, and it's weird to remember that it happened. The last time I went was for New Year's 2007.

Her name was Natasha, and she was a hot eighteen-year-old exchange student from Bologna, Italy. I had just come back from studying abroad in Florence for the semester, and knew a little Italian. My aunt and uncle, who live in Gloversville, NY, had a bit of an addiction to taking on exchange students. There was Irena, Kati, Jose, and I think a few others that came along later. Natasha was their latest and was spending her senior year of high school in the formerly glorious upstate New York industrial city. My aunt and uncle called her their daughter—they still do, to this day. My parents had told me she'd be in St. Croix with us, that I could try out my Italian on her. Honestly, I wasn't thinking anything more than that at the time.

It wasn't just that she was hot. It wasn't just that we saw her running around in a bikini all day on the beach. She had exciting, flirty energy. She would touch your shoulder, engage you, entertain any social advances. She had us all smitten, including the adults.

One older cousin was on the trip—he was 22—and the de facto "brother" of Natasha, as she was living with his father (my uncle). There was 20-year-old me. Then there was my brother, who was seventeen, and my other younger cousin, sixteen years old. My youngest brother and my younger cousin's sister were also there; at ages ten and eleven, they didn't factor into this story.

I don't exactly remember when it happened, but sometime within the first few days of the trip, it became clear that my brother and my sixteen-year-old cousin were engaged in some kind of jousting contest to win Natasha's heart, a Cold War of sorts. No one talked about it. But one of them made a move, and then the other tried to one-up it. My cousin got close to her during a late-night game of Risk. Afterward, we all took a midnight swim, and he wouldn't leave her side. My brother convinced her to take a walk the next day, alone, to the pool building. My brother also plays guitar, and he got up on stage at a restaurant the next night and sang a few songs—always a good move. Later that night he brought her over and "taught her" a few chords. My cousin was sitting right next to them, trying to teach her, simultaneously, how to sing the words (he is in a choir to this day). On and on it went, one move after the next, clear as day. At some point, I talked my older cousin about it, and we acknowledged it between ourselves. I was not involved at that point—of course, she was fun and hot and awesome and Italian, and I spoke a little embarrassing Italian with her, but this was a contest between the younger cousins. I was sitting it out.

New Year's Eve arrived, the final night of the trip. We went out to dinner. I ended up sitting across from her. My cousin was trying to talk to her. Somewhere along the way, her and I started to speak Italian, more than we had up to that point. There was no competing with that. No one knew what we were saying. I think I started to sense something could materialize around that point.

And we all went back to where we were staying for a New Year's party, complete with a DJ. We all started to dance. I wasn't really such a dancer—I felt a bit weird doing it—but she pulled me on the floor and we danced close. I really didn't have to make too many moves. I think my brother had admitted defeat at this point, but my cousin was dogged. He kept coming up to us, trying to talk to her, trying to get in. Didn't he see the battle was already lost?

At midnight we took a swim. The adults had gone back to their rooms. We jumped in, and I had my arms around her. It wasn't a far distance from the pool back to the condo. My cousin, up until the last second, tried and tried and tried, his younger age and his lack of awareness becoming more and more apparent.

Looking back, it wasn't really a fair fight. I was the older cousin. I spoke Italian. And I had inadvertently played it cool the whole trip. If she wanted to have her New Year's Eve kiss, I was the most likely candidate.

Finally, my cousin, after many attempts, went to his room, and we were alone. That's when we kissed, and that's when we showered together, and that's when we spent the whole night awake, locked in some kind of embrace.

I went for a run in the morning with my mom, a common occurrence on these trips. She had seen her coming on to me strongly the night before, had seen the Cold War take shape throughout the week. She asked me about it. And I told her as much as a a son should tell his mother about such things. One thing was clear after talking to her: I knew I'd have damage control to do when we got back.

When I got back, I saw my cousin. He was very clearly avoiding eye contact with me. On my mom's advice, I pulled him aside, and I talked to him. He knew what had happened, of course. He heard us showering together. It was hard to be discreet in a small space like that. And he was angry.

More than that, I think he was hurt and let down. His narrative was that I had "stolen" his girl. Somehow I managed to talk him down, and we ended the trip on fine terms.

My brother was easier. He was a bit more mature, had a little more experience with the ladies. He was basically cool with it. Later in the day, Natasha and I had our final goodbye in the bedroom, and he told me on the plane ride he got annoyed at that final part. But there were no actual hard feelings. He took his defeat graciously, standing up.

This is the part of the post where I'm supposed to get into the moral implications of what I did, of swooping in, of interfering in a contest for a woman that wasn't interested in the participants but whose energy kept them magnetized. I could tell you I feel bad for taking her away. I could tell you it was wrong. But I don't think it was. I only feel good things about the experience. It was all fun, cute, silly, and even though it didn't feel that way at the time, the family building blocks were strong enough to survive such an event.

I went back to New York to continue my junior year of college. Natasha and my aunt took a trip there for MLK Jr. Day, and I saw her in Times Square. We held hands, nothing more. We kept in touch, here and there, and I remember having a long phone chat with her on the first night of my cross-country bike trip as I walked circles around a church parking lot in Portsmouth, New Hampshire. After that, she went back to Italy, and that was basically it. I don't think I ever saw her again.

She's got a couple kids now (at least), and still sees my aunt and uncle. This story is one that lives on in family lore. For a while, my oldest cousin would put on, unprompted, the Rufus Wainwright song "Natasha," and we'd all have a good laugh. And we can all laugh about it now. It is ancient, irrelevant history. My cousin just had his first kid last week (eight weeks early! but he seems to be doing ok). My brother has had many experiences since then. I'm here. Natasha wasn't a major part of my life.

But when I think back to on vacation and having, unexpectedly, a beautiful Italian woman come into my life—well, there isn't much more you can ask for.