One For the Bucket List: Times Square for NYE

By Ashley Dowling

When the new year comes, are we celebrating its arrival on December 31st, or the death of another year? Perhaps it’s the ladder, but as I plan what New Year’s Eve might be like for me, I find myself reminiscing on past experiences. My most memorable New Year’s Eve night was in 2014!

That year, a cousin of mine moved to the United States from Holland. We hardly knew each other, and rarely spoke but for some reason she reached out and invited me to come to her Brooklyn apartment in New York to do the “Times Square” thing. So, hardly knowing this woman, I did what any reasonable person might do – buy a bus ticket. 😉

Celebrating New Year’s Eve in Times Square was a bucket list item for me at the time, simply because the idea of this celebration sounded legendary to me AND I had never been to New York City. If you’ve ever contemplated adding this to your bucket list or striking it out, I’m going to offer you the good, the bad, and the in-between!

First off, Times Square during this time of year is COLD. You’re nestled by the Hudson River and city skyscrapers, so you need to dress accordingly because if you’re serious about doing this thing, you need to be prepared to sit outside in the street for 10+ hours. I’m talking three coats, 4 pairs of socks, mittens over gloves over gloves, and scarves. Too much will probably still not be enough.

The next thing you’ll need to understand is how it can be very boring and at times stressful. You need to arrive in Times Square in the morning. They barricade sections of the streets for people to stand within. Once you enter the barricade, you can leave at any time, but you can never come back. There are no bathrooms, you are a sardine with hundreds of strangers, and there is no food unless you are lucky enough to find a delivery guy running on foot.

Then there’s the music. There’s a New Year’s Eve stage that has a top performer every year. We were barricaded that year near the stage, and it was Taylor Swift performing. We heard her play just a few songs on repeat all… Day… Long…

This probably sounds miserable, and honestly there were moments where we were miserable. Especially when that cold starts to cut deep. But you know what made it worth it? The people we were sardined with. Because you’re all just milling around all day, you have nothing better to do than talk. We met folks from Japan, Australia, Texas, California, Paris, you name it!

I downloaded a game called Heads Up on my phone, and for hours upon hours we passed my phone around the entire crowd and played this game with hundreds of people. These strangers were sharing intimate moments with us, their power banks to make sure my phone stayed charged, their snacks and more in this overwhelming cycle of generosity and kindness. Anytime Taylor Swift got on stage, we begrudgingly had to stop playing because we couldn’t hear our game, and all laughed together about how much we didn’t care about the live music.

Being with all those people and laughing all the way truly was an incredible experience and something I’ll remember for the rest of my life. All the different cultures I had the opportunity to interact with showed me in real time just how similar we all are even if we come from different parts of the globe.

If I could liken this experience to the Financial Aid world, it would be the underlying bones of our industry. There are so many different types of schools out there, so many different areas of mastery. However, we’re all the same underneath our titles and industry expertise. We’re all human beings that are reaching for a world that includes the expansion of knowledge.


At the end of the day, if I were ever to go to New York City again for New Years, I think I’ll choose a place with bathrooms LOL!

I’d love to hear your most memorable New Year’s Eve memory in the comments below!



About the Author:

Ashley Dowling is a Product Manager on a mission to make the usability of software as easy as eating cake. When not immersed in the digital realm – you might find her with a ukulele in hand or a book in lap with her snoozing side-kick Elliot, a Dalmatian/Lab!


  1. Sandi O

    December 22, 2022 at 4:58 pm

    Well said Ashley on our industry. I have a memory of First Night in Boston when I was 20 years old. I wore “flats” on my feat with thin socks. They may have looked great (for 1989) but they were the worst choice for 20 degree weather. I remember we hung out in a bank machine booth to warm up periodically. We also indulged in some spirits to warm up and we’re definitely feeling joyous with our fellow Boston partiers. We were dancing in the streets, admiring the ice sculptures and singing out loud. Boston was super festive. At the end of the night I remember a close friend laying on the ground flat on his back with a big green party horn sticking out of his mouth somewhere on beacon street on a sidewalk. Everyone had to step over him to get by. Needless to say, I forgot about my frozen feet.

    • Ashley Dowling

      December 23, 2022 at 10:38 am

      That sounds like such a fun time!!! Maybe I’m bias, but Boston is one of my favorite cities. I’ll definitely need to plan a NYE in Boston now!


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