Bar hopping and making out with preppies maximized my time during the sticky summer months following college graduation. That June, I'd shoved boxes of clothes and the complete series of Sex and the City into the 500-square-foot apartment I shared with my girlfriend, Kelsey, and started my grown-up life as New York's newest Samantha.

One morning after hooking up with a pair of roommates, Kelsey and I shamefully took the bus home to save money. We rode uptown between old ladies dressed for church still drunk in our matching outfits: a man's sweatshirt, boxers, fishnets and our shiny heels. We giggled over bagels—recapping the details of our alcohol-induced night like my favorite New York quartet would have.

After a decade of watching TV shows like Sex and the City and NBC's new Lipstick Jungle, where women struggle to have it all, I was convinced that Prince Charming would show up in my early thirties once I'd already established myself. At 21, I was determined to double-book dates, clink martini glasses with my girlfriends and live like Holly Golightly (the movie version) without the cat.

As the oldest of three, I'd always been an independent workaholic. Family friends knew I seemed misplaced in our small town outside of Boston; a euphemism for "your daughter is too loud and opinionated." At 16 I told my parents I was moving to New York City. I couldn't be an actress in Andover, Massachusetts. They agreed so I could study theater at Barnard. I parlayed one summer into four hot seasons of interning, working and frolicking through the city.

In New York, I was never embarrassed by my individuality. I bounced around the East Village singing along to my theme song, "La Vie Boheme." I wore tight black clothes, drank coffee, chain-smoked and had my heart regularly broken. I sat in Shakespeare and Co. for hours reading entire plays, sifting through pictures of old New York and flirting with those who did the same.

One night in late July, I met a tall, blue-eyed guy on a friend's rooftop. I tried to seem aloof as I took swigs from my Corona Light. Zach was my type–smart, but not arrogant, and more interested in playing his guitar than talking to me. He was 22, but only a month older, and had freckles on his nose. By midnight, our mutual friend had ditched us for her drug dealer and we were alone. We played unsuccessful rounds of the name game before he finally asked me: "What do you write?"

"Plays about apathetic WASPs," I responded quickly trying to avoid follow-up questions. I hated talking about my work especially because I was hardly writing. Sitting in an office for eight hours a day had proven to be uninspiring. I preferred dating and drinking to spending time in my claustrophobic apartment at my computer.

"I'm borderline obsessed with skylines thus the real estate thing," he said staring into the lights from downtown.