My very first time in New York City was May 1, 1999.
I’d just finished my sophomore year at the University of Michigan, and my college boyfriend invited me to visit his childhood home: a two-bedroom apartment in a doorman building on the Upper East Side. Since I had grown up in the Michigan suburbs with a swing set in our backyard, this felt very foreign.
I was wildly intimidated by Manhattan. I had been to cities before, of course, but New York felt like something else entirely. The maze of streets were riddled with people and dogs and cabs and bodegas. I felt high as a kite; I loved everything about it. Two years later, after graduating from college and saving up, I moved to New York City in October 2001.
It’s funny to think back on the past 20 years of your life. Have you ever tried it? Here are some snippets from mine…
October 13, 2001 — A guy friend and I move into a tiny apartment sublet. He gets the bedroom and I sleep in the living room. The sofa doesn’t fold out and there are cockroaches and I eat spaghetti every night for dinner. But, NYC, it’s on.
October 15, 2001 — First day at Cosmopolitan Magazine. My assignment is to stop good-looking men on the street and ask them sexy questions. “Not just regular cute,” my editor tells me. “They need to be so cute that the reader stops turning the page.”
December 12, 2002 — Interview at Vogue. Have a tag sticking out of my shirt. Don’t get the job.
August 2002 to August 2003 — The Year That Dare Not Speak Its Name. Not sure what to do with my life, I enroll in law school at NYU. I buy the books with a heavy heart. I have a hard time connecting with classmates and feel awkward and weird. My dorm room is on the ground floor, and the window looks onto a food cart on Broadway; it smells like hot dog water 100% of the time. I’m going through an excruciating year-long breakup with a college boyfriend and my heart’s in a blender.
August 15, 2003 — Decide to leave law school. Get three jobs to help pay off the loans. Have never been happier.
September 8, 2003 — Funny we’re-not-in-Kansas-anymore moment: I’m now working at a boutique editorial firm, and my boss loses her $300 Hermès pen somewhere during a morning outing. She comes back to the office, very emotional, and asks me to track it down asap. It’s like finding a needle in a haystack — except it’s an orange pen in Soho. (Spoiler: I find it.)
September 24, 2003 — In the evenings, I teach the LSAT for Kaplan. During a class, I realize that one of my students is drawing portraits of me instead of taking notes. He asks if I will tutor him outside of class, but instead of meeting at Kaplan, he suggests a downtown bar. He wears a shirt and tie. We start dating.
April 12, 2004 — Get a bike!
September 14, 2006 — Move to a third-floor apartment with a roommate in the West Village. Catch 17 mice in three months. Adopt a cat.
November 25, 2006 — After three years, my boyfriend and I break up. He’s funny and smart, but I just don’t see it lasting. We meet at a restaurant to say a final goodbye, and he tells me he has a ‘parting gift.’ It’s an iPod, and when I flip it over, the engraving says, “You’ve made a terrible mistake.”
December 13, 2007 — Winter feels dark and lonely.
January 1, 2007 — Start a blog to distract myself from feeling sad. My brother jokes that I should call it “Cup of Jo.” I do.
February 14, 2007 — Worst Valentine’s Day. My jeans get soaked in a giant puddle on my walk home from work, and I wonder if, for me, love’s just not in the cards.
February 25, 2007 — Meet a cute guy in glasses at a party. Hmmm.
February 27, 2007 — Roll the dice and email the guy with glasses.
March 2, 2007 — Go on a date with the guy with glasses. Have a dreamy first kiss on Bleecker Street. Passersby call out, “Look at the lovers!”
August 11, 2008 — Start a job at Glamour Magazine.
October 31, 2008 — Get engaged to the guy with glasses!!!
December 30, 2008 — Ride bikes with my brother to the J.Crew in Rockefeller Center. Try on wedding dresses. Pick this one.
August 28, 2009 — Get hitched.
September 15, 2009 — Walking home from dinner, I stop by the CVS in the West Village. On a lark, I buy a pregnancy test. It’s positive.
April 2, 2010 — Being pregnant in NYC is exciting. People on the street call out, “Hi, Mama!” and cab drivers guess, “Seven months? Eight months?” After almost two years, I tell Glamour that I’ll be leaving to focus on the baby and Cup of Jo.
May 25, 2010 — Baby Toby arrives. Everything changes.
April 1, 2013 — Tobes starts talking; turns out he’s hilarious.
July 5, 2013 — Baby Anton arrives. After meeting his brother, Toby muses, “I want to see him again sometime.”
September 17, 2013 — Burst into tears at the playground because parenting two tiny children is hard. A guardian angel mother walks over, hugs me and tells me it gets easier.
January 1, 2014 — It gets easier.
August 1, 2014 — Move the fam to Brooklyn. Alex’s first time seeing our apartment is move-in day. (I had gone to the showing by myself, and apartments were renting so quickly that we had to make an immediate decision.) Luckily, he likes it.
Since then, we’ve bought a home, considered a third baby, muscled through haircuts, gotten locked out, thrown parties, lived with anxiety, celebrated birthdays, and done all sorts of random things in this crazy town we love so much.
Last week, I went to the East Village to see my friend Reagan. “Walking around the city is so funny,” I told her. “I always see some guy riding a skateboard with his dog, or a little girl playing a harmonica on the sidewalk.” Laughing and nodding, Reagan agreed: “In New York, everyone’s the main character in the movie.”
New York, I love you. Here’s to the next 20!!!