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Home  >  Trip Reports  >  New York City – First Date
Trip Reports

New York City – First Date

Kyle Stewart Posted onFebruary 19, 2013September 16, 2021 1 Comment
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Descending into New York City

Keeping up with my UN-Trip Report, it doesn’t get less “trip reporty” than this. The rest of the details of our trip will come soon, but this has it’s place, right here, right now.

————–

There is a strange excitement for travel that only comes with traveling to a new place. It’s kind of like a first date, it can be a little awkward as you find your way around making things both enjoyable and from time to time uncomfortable.

But no one forgets the thrill of a first date. My first date with my wife, the Sherpstress, was as awkward as could be. It was a day date (both of us occasionally worked nights), and I knew she was coming from a funeral (very romantic, I know) so it really couldn’t have been a more uncomfortable setup. We both clearly wanted to see each other and it didn’t really matter to us that it was over sandwiches instead of candlelight.

To make her feel more comfortable, I dressed up, jacket and tie as if I too had come from a funeral so that we wouldn’t be at the table looking like two misfits. She had the same foresight however, and brought a change of clothes so that I wouldn’t feel uncomfortable.

So there we were, me in a suit, and the Sherpstress in jeans and a t-shirt trying our best to impress because we both really wanted to be there.

This brings me to our current trip. In 184 cities, 34 countries (many of them several times) on six continents, none of them included stepping foot outside in New York City. It had always been cheaper overall to go to London and it seemed some much more adventurous to make it to Europe as opposed to some place, seemingly everyone I had ever met had been.

But that changed. I started to see NYC as a really incredible city, important to my understanding of my own country and how I fit into the world. My travel resume was also seriously flawed without even a cursory visit to New York.  So we booked it.

And now as we begin to descend I’m nervous, excited and ready to fall in love with the place.  I’m sure I’ll make blunders and miss important sites, but that’s allowed on a first date. Who knows, maybe it will be forever, just like my last first date.

-Sherpa

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About Author

Kyle Stewart

Kyle is a freelance travel writer with contributions to Time, the Washington Post, MSNBC, Yahoo!, Reuters, Huffington Post, MapHappy, Live And Lets Fly and many other media outlets. He is also co-founder of Scottandthomas.com, a travel agency that delivers "Travel Personalized." He focuses on using miles and points to provide a premium experience for his wife and daughter. Email: sherpa@thetripsherpa.com

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1 Comment

  1. Bruno Reply
    January 11, 2019 at 7:48 pm

    Aaaaaaaaaaaaaaawwwwww this is ADORABLE! Just like you, NYC was a gaping hole in my travel resume that I was so excited to fill, just like your first date! I’m looking forward to my second date with NYC because it was definitely love at first sight!

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