If You Put On A Sailors Hat… A Cautionary Tale. 

It’s Fleet Week in New York City which means men and women in military uniforms flood the bars and tourist attractions around town and the jokes about “seamen”and “semen” being interchangeable words begin. US navy vessels have made stops in NYC since as early as 1898 and since 1982 the Navy, Marine Corps and Coast Guard all dock in New York City for one week right around Memorial Day weekend. Once the ships dock, the crews can enter the city and visit its tourist attractions and the public can take a guided tour of the ships. The men on these boats all want to meet some young ladies and and the ladies of New York are attracted to a man in uniform. Think of the famously snapped picture of the navy sailor kissing a women in the heart of Times Square. It’s kind of romantic and very American. However I don’t think any of those sailors are looking for romance. 


In May of 2007, my childhood friend Natasha flew to New York for the weekend from Colorado to see some sights and visit. On the Tuesday after Memorial Day we went down to the Intrepid, hoping to get a tour of the boats and flirt with those navy boys. 

That’s exactly what we did. We saw all kinds of fancy military machines, none of which we actually found interesting but we pretended all the same. Our last stop was the top of the boat where we could see Navy planes and as you might guess, we met two navy pilots. It wasn’t busy on the boat by Tuesday and so we got special treatment. After our tour and some innocent and youthful flirting, it was time to say goodbye. Just before we could leave, one of them mustered up the nerves to ask me to meet him later for a drink. My Nana had met my Papa in Times Square during fleet week almost half a century ago and me, always being one for a cute story, agreed to the date. I was 21 and single. Why not!?


And so, later that night I trekked downtown via the subway dressed in a summery halter dress feeling good about myself to meet the navy pilot. We met in the heart of Times Square and found a bar with a table right at the front window. It was one of those over priced spots that the locals avoid at all cost and this poor guy probably paid $12 for my poorly chosen amaretto sours. At this point in my life, I had never actually been on a date. I’d met people but never really dated any because I never had an interest. I felt nervous, excited and somewhat rebellious. I was meeting a perfect stranger in Times Square for a drink! How adventurous!

We settled in right away, chatting about where we were from, our interests and where we planned our futures to go. We definitely clicked right off the bat and our banter was fun and effortless. As this was 11 years ago I can’t recall how long we were together, I’d imagine a few hours but it felt like minutes. Before we knew it, he had very little time to be back on the boat before curfew. I’m sure there was some sort of horrible punishment for being late because he had a great level of urgency as he paid the tab and debated walking or taking a cab. As he stood at the bar to pay the tab I put on his fancy navy hat thinking I was being cute. When he returned to the table, I think he thought he was being cute when he told me about the unwritten rule about putting on a sailors hat. Supposedly in exchange for the hat on my head, I owed him a kiss on the lips. I realize now he fabricated that rule but my younger self fell for it. Like two teenagers, we nervously leaned in to each other and as you could predict, we kissed. There were no fireworks but it was sweet and we both felt the thrill and excitement that comes with that first kiss. He so sweetly thanked me for meeting him that night, repeatedly saying I was the best part of his week in NYC. His crew (I don’t know the official Navy terms) was to leave the next day and very soon after that he would be somewhere overseas. We exchanged email addresses and as I watched him drive away in a yellow cab back to his ship, I knew I would never see him again. 

As I rode the subway back home that night, I felt light. I felt good. Meeting him that night was a step out of my comfort zone and it went better than I imagined. Though the Navy Pilot and I had no future, he reassured me that it was ok to open myself up to people a little and nice guys do exist beyond those high school sweethearts. Though it was brief, it was a special; one of those memories you hold on to for a lifetime. 

The Navy Pilot and I kept in touch via email for a bit, updating each other on our lives and often wrote about if our paths would ever cross again someday. Four months after meeting my pilot, I met my fireman. After that, our emails became less and less. Thanks to good old facebook, we were able to reconnect a few years later and through that I learned he was back for good with the Navy and he was dating a girl he liked very much. They later married and though I’ve never met her, they are one of those couples you can just tell are perfect for each other. It’s just very authentic and very obvious. They very recently, I think just last week, had their first baby girl and he appears to be as happy as you could hope for someone to be. 

I’m thankful for that night in Times Square and thankful to have met him. Our story had a very clear beginning and a very clear ending but it was meant to be none the less. As dramatic as it may sound, that night helped shape in some small way the adult I’ve become today and for that I am filled with gratitude. Plus I learned a valuable life lesson. If you put on a sailors hat, you better be prepared to pay the price. 

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