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St. Thomas Travel Guide

I Went on a Blind-Date Vacation With Someone I’d Never Met

It may not have been true love, but it made for a heck of a story.

Societal pressures tell us we’re on a timeline regarding dating. If you think dating in your 30s is difficult, try adding a global pandemic that limits human interactions and forces you to create any sense of intimacy through a screen. The pandemic has shifted our everyday human interactions (sometimes for the better) in ways that limit simple things, like going on first dates or establishing a connection with someone beyond the screen. Things like testing out the vibes and seeing if a person is a better friend than a lover have become more elusive than usual and sometimes require daters to go above and beyond to get any result.

Take, for instance, my dating life before the pandemic. As a single person in their mid-30s, I would meet people online and then suss them out on a first date somewhere casual and non-committal. The pandemic changed all that, and my meet-to-greet process was altered into an endless meet-and-meet loop.

It was a welcome surprise when someone I had chatted with pre-pandemic slipped into my Instagram direct messages in late October of 2021. I had already passed the beginning phase of introductions and wouldn’t have to be in a never-ending circle of dating application chats. The conversation flew, and it seemed like I didn’t need to spin myself in the most flattering light. I had already done that with them, and it felt great having to chat with someone who somewhat knew me.

​Around that same time, I planned a visit to the island of St. Thomas and coordinated a luxurious hotel stay at The Ritz-Carlton. I thought it would be interesting to invite my would-be suitor on the trip. ​Normally I would never take a vacation with a perfect stranger, but the pandemic had changed the game.​ Half expecting them to say no, I presented the idea via our direct messages. A few days later, I received a reply from my potential suitor that they would like to join the trip. At that point, I begin to panic.

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The cruel reality of spending four days with a stranger roused crushing anxiety in me. The only thing that absolved the high level of concern was the thought that crazier things had been done to find love, and I was ready—even if I could potentially be murdered.

The smoothness of the process helped ease my fears. Through private transport, I arrived at The Ritz-Carlton on St. Thomas and was met with hospitality common of 5-star resorts. I was addressed by name without introducing myself, making my panic lessen. Checking into the room, I was impressed by the updated beach decor that laced every corner of my suite. Subtle nods of wicker in hanging lamps and chairs gave the room a strong juxtaposition between the old beach and the new. I nervously waited for my date, coming in from a different flight, counting down the minutes as they texted me they were getting closer and closer.

After giving them my room number, I heard a knock on the door. My heart raced as I went to answer, and the thought of encountering a giant catfish kept running through my mind. I opened the door and was suddenly lip-locked with a stranger I thought could be the immense love of my life—or its end.

Emy Rodriguez

We spent the next few days getting to know each in St. Thomas and the resort. We enjoyed a cabana by the recently updated pool and toasted with painkillers, the local rum-based drink created in the Virgin Islands. We even boarded a sunset sail cruise that the hotel had arranged. Everything was perfect, and even when we took a charter ferry to the neighboring island of St. John, it felt like a never-ending fantasy.

While bathing in the heaven-like beaches of Cinnamon Bay, we caught the attention of a couple who approached us and began a conversation. They asked where we were from and how long we had been dating. My date and I paused for a second, unsure how to respond. We explained how this was our ongoing first date, and we were still getting to know each other.

The confusion from the couple was palpable. Reality finally shook us from the fantasy, and no amount of painkillers could loosen its grip. On our plane’s descent back to the mainland, we realized there was no way we could make a real relationship work. I lived in Miami and they in New York; not an insurmountable distance but enough to make growing a relationship difficult. In the end, we may not have been destined for true love, but I survived a blind vacation date and walked away with a story I’ll never forget.

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