15 Years in NYC: Adult Bunk Beds, Tipsy Piercings, and Roommates in Your 30s
I can’t believe it’s been this long, to be honest…
On June 16, 2010, a one-way ticket brought me from my hometown of Seattle to New York City. Fifteen years later, I think of Manhattan as my other hometown.
In sitting down to write a bit of a reflection on this milestone, I was a little bit stumped. What do I have to say about New York that hasn’t already been said, and many times over?
Realistically, probably not much. The things that appeal here — and the things that appall — are aligned for most of us. Restaurants! Rats! Walking! Waiting in line! Bagels! The old Penn Station and the new Penn Station.
Instead, I thought it would be fun to comb my memory files to try and shake out the little things that have made living here work for me for so long, and why it’s been an absolute blast.
So let’s do that!
My very first job here was pouring wine on a sunset sail around New York Harbor.
Only a few weeks into my NYC tenure, a friend of a friend connected me to a wine shop, Pasanella & Son, to possibly work the register and make a few bucks.
Instead, the manager set me up as the shop’s representative on a weekly sip-and-sail sunset cruise around New York Harbor. Every Thursday I’d turn up at the shop and get briefed on the three wines being served at sea that evening.
Once aboard, I’d introduce myself to the guests and give a little elevator pitch for each variety. Then it was two hours of chit-chat and pouring as we toured around the Statue of Liberty and Governor’s Island. I got paid $50 plus tips.
The best part of this job was that the manager let me take home any opened and unfinished bottles of wine, as well as any leftover Granddaisy Bakery flatbreads that weren’t consumed. My roomies and I were 24, broke and thought this was the coolest thing ever.




I was a style blogger.
I started my style blog, SHUT UP I LOVE THAT, in 2009, because my dad told me it was going to be the next big thing. I had no idea what doors it would open for me over the next decade. It got me jobs, it got me paid, it introduced me to some of my closest friends, and taught me how to be a low-level entrepreneur. I got to work with amazing brands, attend fabulous parties, and got quite a lot of free stuff, which, at that time, was an unbelievable treat!
Running around New York taking photos, mingling with other bloggers and documenting my adventures — press trips, Hamptons weekends, concerts, restaurants, even dates — was such a core part of my early life here. I would be a different person with a different life without that side hustle, and it’s the inspiration for starting this newsletter!
The infamous “adult bunk beds.”
We were four girls in a three-bedroom apartment on Chelsea. One had a well-paying job, and the rest of us… Were figuring it out. And so we devised a scheme to make our living arrangements more affordable.
I bought a queen-size mattress from one of the girls moving out of our apartment (I shudder to recall), and my roommate Moira and I purchased a full-size Ikea platform frame off of Craigslist to accommodate her mattress. (Which our downstairs boy neighbors helped us put together once we’d brought it home in a taxi.)
For two years, the three of us rotated every four months between the queen, the full, and the second bedroom with its full bed and closed door. We would drag our dressers on towels from room to room when moving time came, and carry armfuls of dresses on hangers. It was a glorious and goofy time I wouldn’t trade for anything!
Having a Halloween birthday.
The time has come in this newsletter to out myself as someone who loves their birthday. I love attention! But more importantly, I love getting all my friends together and partying. Especially in costumes.
For five solid years in a row, I hosted my birthday at Bar 169, which at the time was a very IYKYK bar for getting way over-served after 1 am and consuming massive amounts of steamed dumplings from takeout boxes. We were often the only people in costumes, lol.
Eventually, my annual themed birthday party, hosted at “The Penthouse,” by Frank and myself, became a tentpole event on the social calendar for our whole circle. Themes included: Yeehaw 34, 1985, Space Disco, You Can Sleep When You’re Dead, and Royal T. (I may have devote a whole newsletter to theme parties in October?)
These epic house parties defined an era of my life in New York. We danced until 4 am, played flip cup on our patio and decorated every inch of our wonky East Village walk-up. (My number one decorating tip is to buy at least a dozen of these — they make any room look festive and photo-ready!)


Working on The TODAY Show.
For several years, I worked with the iconic Bobbie Thomas, helping with on-air segments, social media and all kinds of miscellaneous moving pieces. I also styled a couple of on-air fashion segments myself, which was a career highlight.
We all move to New York with big dreams, having no idea which ones will come true. I never thought I would be able to say that I worked both behind and in front of the camera on a national morning show. It’s a little surreal to think back on, even now!
Getting piercings on St. Mark’s after a boozy brunch.
In the mid-2010s, this was pretty much a right of passage for the downtown girlies. It was a time when “bottomless brunch” was really that, and it was cheap.
On a Sunday afternoon, likely hungover from dancing all night at Gallery Bar or staying too late at Max Fish, my pals and I would have a debrief and get festive with a few too many mimosas in Alphabet City. On our walk home, we would, from time to time, feel that the only appropriate thing to do next was pop into a tattoo and piercing shop on Saint Mark’s.
In the past fifteen years, I’ve gone from two ear piercings to eight, and I‘ll leave it at that!
Drawing classes at the National Arts Club.
When you live in New York, pursuing great cocktails and dinners out could be considered a hobby. It’s fun, cultural, and communal, after all! But as it turns out, there are other fun hobbies you can engage in here in the city, and in fact, you can pursue one of them at a historic members-only club across the street from the only private park in Manhattan. (Gramercy Square Park, of course!)
The National Arts Club is indeed private, but you can pay about $30 and attend figure drawing classes for all abilities that are open to the public — with a nude model and a groovy soundtrack — in a historic and gorgeous little room with creaky wooden floors.
A couple of friends and I have been taking these classes once a month or so, and it’s the most enjoyable and creative way to spend an evening. We usually down a quick drink at Pete’s Tavern before class and then have a lovely late dinner at L’Express afterwards. A perfect New York night!
Taking the ferry to Rockaway Beach.
Sometimes it feels like doing something in New York is more difficult than doing that same thing anywhere else. Going to the beach is one of those things. (The grocery store is another. The Trader Joe’s experience here is truly criminal.)
However, I’ve come to love the schlep of getting to Rockaway Beach. I love to wake up early, pack my French market basket, order a big hoagie from the deli downstairs and take a taxi to the Wall Street ferry launch. I love sitting on the top deck for an hour — sometimes with a bootleg mimosa and a bagel, sometimes with a podcast and a far off look in my eyes.
You’re surrounded by people, all with the same happy feeling — because it’s hard to be anything but a little bit giddy when you’re heading for the beach. We’re all in it together, carrying heavy bags and umbrellas and traveling for ages just to stick our toes in the sand for a few hours.
Dinner parties in a bedroom.
The Penthouse apartment I lived in with Frank (and Caitlin before him) had a bit of magical energy. It was small, strangely shaped and not at all modern. The only place that fit a dining table was Frank’s oversized bedroom, and he brought one all the way from Portland, Oregon when he moved.
That table became the setting for multiple Thanksgiving orphan feasts, plenty of covid-era cooking experiments, game nights and more random, wine-soaked weeknight dinner parties than I can count.
The quirky setting was cozy, intimate and made for unforgettable gatherings that, in hindsight, feel like those “only in New York” moments you want to tell your grandkids about. They are some of my most cherished memories.

Having a roommate well into your thirties.
I had never lived alone in my life until I was 38. I love this about myself. As an only child, I have always said that I got my fill of solo time as a kid, and haven’t needed much of it since. And while I do enjoy the control and adult-ness of having my own place, I would happily live with friends again in a heartbeat.
In New York (as in many big cities), you can swerve the traditional markers of a grown up life and still be a grown up, perceived mostly without judgement by your peers. You don’t have to have a mortgage, a marriage, a car payment or a kid to reach your most evolved form.
And for me, living with friends as an adult, in rented apartments where we threw absolutely wild parties and cooked fabulous meals and grew a little garden and nursed hangovers and had pet fish and shared gossip and lost jobs and got boyfriends — that shared living experience has meant more to my New York life than anything else.
That’s all for this week, thank you for coming down memory lane with me! I’d love for you to drop a comment with your favorite NYC memory below.
So good Taylor!!!