I Spent A Week Living Like A Millennial In 2016

2016 is back. Lately, Instagram and TikTok have been a treasure trove of nostalgia for “millennial optimism,” and much of it is actually from Gen Z, yearning for an adulthood we narrowly missed. Everything from the music to the clothes to the way people posted on social media without a care in the world, just seemed better back then. Compared with today, when AI music is taking over our airwaves, unique outfits beget Amazon Storefront dupes, and nearly every TikTok trend falls victim to an endless cycle of online outrage, the millennial heyday just seems so blissfully hopeful.

The life Lena Dunham broadcast in Girls was chaotic, and her disciples’ schedules were packed. As I’ve gleaned, millennial New Yorkers apparently went out on Thursdays and sweated out their hangovers at SoulCycle at the crack of dawn on Fridays. That’s the adulthood I expected when I moved to the city for college in 2020, and back again in 2025 after a stint in my tiny Massachusetts hometown.

But that energy seems to have disappeared. After-work happy hours are few and far between — most of my friends and I work in person rarely, if ever. The thrill of going out on the weekend is often dampened by TikToks from #CleanGirl influencers, who cut out drinking and tuck themselves into bed by 8 p.m. every Friday night.

I wondered: Could I handle the go-go-go lifestyle of the 2010s? Me, who has never worked in an office more than one day a week? Me, with a passion for cancelling plans? After consulting with my most trusted elders, I loaded my schedule with everything from avocado toast to an indie show at a Brooklyn dive to, yes, business-casual clubwear. Ahead, I took it back to 2016, and I lived like a millennial for a week.

Monday

I wake up at 7 a.m., an hour and a half before I usually roll out of bed — rise and grind. I get dressed (not always something I do while working from my couch), and do my makeup in the way of my foremothers: winged eyeliner and a nude-toned matte Kylie Lip Kit. It’s a heavier look than I would typically wear, but the end result is not nearly as bad as I expected. Clean girl? No. But cute? Wearable? Sure!

Next, I head to The Commons, a co-working space that agreed to host me for the week. When my friends and I talk about work, the conversation nearly always leads to us mourning the office culture we never had. What we would give to have actual watercooler chats with our co-workers instead of just hoping our Slack joke lands. This sentiment is far from unique: A 2025 Gallup report found that Gen Z is the generation least likely to prefer remote work.

While a co-working space doesn’t necessarily invite socializing the way a shared employer does, The Commons tries to bring people together in little ways, like leaving puzzles out to be solved collaboratively over coffee breaks. Still, the space is mostly quiet, besides the odd Zoom meeting taken in hushed tones. I finish my to-do list undisturbed.

After work, I grab my roommates and a bottle of Summer Water rosé and sit back for a few episodes of Girls. A few minutes in, Shoshanna admits to Jessa she had done something “kind of crazy”: made an “Internet dating profile.” Inspired, I decided it was time to set up an account on 2016’s go-to app, Tinder.

I attempt to make my profile as historically accurate as possible, writing “5’4 if that matters 🙄” and “message me if you also love the office and pineapple on pizza 🍕.” After some disappointing swiping and a few more episodes of Girls (Marnie’s lipstick was visibly dry), I go to bed.

Tuesday

For lunch, I take off on a mission to find the quintessential millennial meal: avocado toast, once maligned as the reason that generation would never be able to afford a mortgage. (Plot twist: 55% of millennials are now homeowners.)

I land at Jack’s Wife Freda, a brunch spot that was trendy in the mid-2010s, and order a $19 “mashed avocado on seeded bread” and a cold brew. Sue me, I’d rather direct a spare $20 toward a slice of avocado toast than toward my student loan debt — my loan servicer does not provide a delightfully tangy tomato jam topping.

After work, I head to Poiz Beauty Salon, where I’d booked a 20%-off mani-pedi through Groupon. Millennials might have been chastised for their spending habits, but the generation was also adept at sniffing out deals on sites like Groupon, Classpass, and MoviePass. I leave with a fresh set and advice from my manicurist, Yuliya, to stop lugging around my overfilled tote bag before I give myself back problems.

Wednesday

You won’t believe it — I have real plans after work. At the end of the day, I stop by my apartment to throw on my indie-sleaziest look: a black top, the lace-up Doc Martens I begged my parents for in high school, a red matte lip kit, and a side part. The final result is not particularly sleazy — I think my millenial-sona is more Zooey Deschanel than Alexa Chung.

Then, I meet up with a friend to catch a showcase of local bands playing at Union Pool, a bar and concert hall that multiple sources confirm was a go-to spot for millennial Brooklynites. It maintains its popularity amongst 20-somethings today (meaning it’s saved in my “places to go nyc” folder on TikTok). I order an IPA for the bit and immediately regret it.

The Wednesday night crowd is somewhat sparse and leans 30-something — a group of self-described millennial women tell me they avoid the bar on weekends, when Gen Z takes over. The main act is RIP Dunes, with sets from Marjorine and Cowboy Clean, and it’s exactly what I would’ve expected from an indie show at a Brooklyn bar: men with mustaches performing drum-heavy folk rock with a little bit of synth. I headbob along with the crowd, and take a few photos, imagining how many reblogs they would’ve gotten on Tumblr in 2016.

On my way home, I meet my editor to borrow some authentic millennial swag to wear for the rest of the week. On the subway home, I craft an Instagram post, cranking the Valencia filter up to 100. Post to feed.

Thursday

Before I clock in, I head to Dominique Ansel Bakery to get a taste of the iconic cronut. The doughnut-croissant hybrid became a fixture on square-shaped Instagram feeds when a 2013 blog post launched it into viral stardom.

Dominique Ansel is still cranking out its signature today — in fact, the bakery concocts a new flavor every month. When I stopped by, the flaky pastry was filled with hojicha, a Japanese black tea, and Okinawa black sugar ganache. Not every viral food trend is worth waiting in line for, but there’s a reason the cronut is still around over a decade later. Beyond being photogenic, it’s pretty damn good!

Later in the morning, I’m back at the co-working space in a blazer and a very Blair Waldorf-coded plaid headband. I like that I recognize some of the more frequent visitors, and that the two front-desk workers know me by name, even if people mostly keep to themselves. During my lunch break, I stop by a community vision boarding event in one of the larger meeting rooms, where a handful of therapists discuss their 2026 goals over chips and dip.

Twice in a row now, I have social plans after work. I meet some friends for a happy hour at Somebody’s Darling, a bar drowning in millennial memorabilia. “Butterfly” by Crazy Town blasts over the speakers as we try our hand at vintage Ms. PacMan and Streetfighter II arcade games. My hectic schedule has me feeling decently exhausted, but as we sip our drinks, we plot next week’s happy-hour excursion.

Friday

When my alarm goes off at 5:45 a.m., I am profoundly confident that my soul will leave my body. I’m up before the sun for one reason only: a Taylor Swift- and Miley Cyrus-themed SoulCycle workout, booked through ClassPass.

The boutique spin studio’s cultish reputation precedes it. I know I’ll be leaving sweaty. The riders in the front row seem practically professional. The instructor, Lisa, was the most awake I’d ever seen someone at 7 a.m., interrupting “The Fate of Ophelia” to encourage the class to “pledge allegiance to your core!”

After class, I return to my apartment to shower before heading to a new work location: Café Grumpy, a Brooklyn coffee shop featured on Girls. I order a latte and a muffin and take a seat, watching as millennial customers in chunky-knit sweaters filter in and out, and order, to my surprise, mostly whole-milk beverages.

That night, my roommates and I host a party at our apartment — part of a commitment to “be the village.” I’m not sure whether COVID, Gen Z introversion, or rent prices killed the house (or apartment) party, but it is my belief that we should individually do all in our power to bring it back.

By the time the last guest leaves at 2 a.m., I’ve tipsily expressed my undying gratitude for everyone’s friendship. With “New Romantics” playing on Spotify, the day ends as it began with me listening to Taylor Swift, about to fall asleep where I stand.

Saturday

It’s time to really hit the town. While millennials pioneered so many aesthetics, from emo to twee, their most iconic look, in my humble opinion, was business casual at the club. I wear a fitted, ribbed sweater dress borrowed from my editor, with a long pendant necklace, chandelier earrings, and yet another headband. I also put on kitten heels because nothing I own matches the stratospheric heights of millennial clubbing shoes.

I’m not much of a club girl, but after some light pregaming (soundtracked by Views by Drake and Starboy by the Weeknd), my friends and I landed at Marquee, where we danced, or more accurately, headbobbed the night away to an EDM set (some stereotypes of Gen Z are pretty accurate). Am I a club convert? Probably not — but I gained a sincere respect for millennials who partied far harder, and in platform pumps.

Sunday

I scarf down a bagel and throw on a floral slip dress, layered over tights and a white T-shirt, and force my hair into a deep side part before venturing to a brewery in Brooklyn. Although Talea opened in 2021, the women-founded and -owned brewery looks like it’s straight out of the #girlboss era, from the teal and millennial pink color scheme to the quirky variations it has on tap. (I tried the rainbow cookie-flavored beer — it got this nonbeer-drinker’s stamp of approval.)

I have one final stop to make. Back in the day, everyone and their mother seemed to have a picture posing on a cobblestone street with brick buildings perfectly framing the Brooklyn Bridge in the background, and I was ecstatic to join the ranks. The trek takes an hour, but what can I say? #WorthIt.

As my week of millennial living comes to an end, I’m tired. I’ve spent an unprecedented amount of money taking the subway, and my lips are in serious need of hydration. But also, I’ve had the most fun in a single week I’ve ever had since I moved to the city in 2020. My schedule was relentless, but I saw friends nearly every day and got to explore new neighborhoods. I did things before and after work! I got regular compliments on my lip kit! And, I only lost two followers while posting my Valencia-filtered photos on Instagram.

I discovered that with some time, effort, and bargain-hunting, millennial optimism is still possible to a certain extent. How could you not feel a little more hopeful when you’re constantly doing things that bring you joy?