Myself And The City

After my first few lackluster dates in the city of dreams, I couldn’t help but wonder, would I ever find my person?

But then it hit me. I realized I’m not Carrie Bradshaw. Being loved and loving someone else in return is all I wanted, but I’m not ready for that…

If I don’t fall in love with myself first, how can I ever expect someone else to?

So with that, I threw out the rulebook that says you can only go on dates with other people, and decided to date myself. And honestly, it was my best first date ever.

A little over a week before my birthday, I reserved a table for one at Upstairs. A rooftop bar nestled in Midtown East with views of the Chrysler Building and surrounding skyscrapers, Upstairs is self-described as “focusing on refined service in a relaxed luxurious setting, offering its guests a one-of-a-kind rooftop experience and the desire to come back again and again.”

The entrance to the bar is inside The Kimberly Hotel. Upon arrival in their lobby, I was guided to the elevator where I was then taken to the Penthouse level. After giving my name to the host, I took a seat at the bar, where I people-watched until my table was ready.

The partially-shaded bar area offered an impressive view of the city, and there were already around thirty guests mingling and drinking, some in dressy work attire, some in the official dress code of Business Casual. I myself wore a semi-casual sundress, duster cardigan, open-toed pink block heels, and gold jewelry. From what I could tell, the ages of the other patrons ranged from mid twenties to fifties.

The host returned to take me to my table in a private area with an even nicer view of the city. Due to COVID restrictions, there was empty seating between me and the two men to my left, who were dressed in suits. Across the room sat a table of eight twenty-something-year-old friends in semi-casual outfits, and beside them sat two women wearing work attire. For a Tuesday evening, Upstairs had accumulated a great crowd.

I already knew what I wanted even before my waitress asked: the Upstairs Strawberry Rossini, which is a blend of vodka, lemon, strawberries, basil, and cava. The moment I saw it on the QR code menu at the bar, I knew it was for me. I’m a lover of sugary cocktails.

One nice thing about dating myself? I can order as many cocktails as I want without a look of dismay from a date who feels the need to pick up the tab. I only ordered two, but even that number would have resulted in wide eyes and a comment of disapproval from my ex.

For dinner, I ordered the grilled lamb chops. They were truly a “small plate” meal but still delicious. You don’t go to Upstairs for the food, anyways. You go for the cocktails, ambiance, and view.

On my first date with myself, I scrolled through my phone, read a book, and enjoyed the view in peace. No awkward date with forced small talk. No cheap meal ordered only to satisfy someone else. I could actually, truly enjoy myself.

And you know what? I’m already looking forward to the next date.

Outfit Of The Date:

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