How did we get here?

This is a question I ask myself a lot. Don’t get me wrong, I love my life; but it’s not exactly where I saw myself in my mid-twenties. I’ve been in NYC for 2 and a half years and I’ve been single for about 6 months. When I moved to the city, I was still dating my college boyfriend. He was staying back home to finish school and we were going to be the couple who made the long distance thing work.

Here’s where you can say “I told you so,” because after 2 years of great weekend trips, phone fights and changed life plans, we ended things. I hadn’t been on a first date in almost 4 years, so I relied on my friends to help me figure out how to climb back on the dating horse.


After a hazy weekend away with friends, I decided I was going to try to meet people IRL before going on the apps. Two weeks post break-up on a Friday night, my roommate (Sarah or S, as I lovingly call her) dolled me up for a pre-game and night out I was attending, where there promised to be eligible bachelors. Right before I left, she said, “you’re totally get laid tonight” and I laughed in her face.

The pre-game was on a great rooftop in Murray Hill, where the wine and beer was a plenty. I met a few of my friend’s friends, but everyone I talked to seem to be in a relationship. They were fantastic people, but not exactly how I was hoping my first big night out as a single woman would go.

Finally, I was introduced to the host of the party, and let’s just say, that he checked all the boxes. Handsome, successful, funny…SINGLE. We hit it off, he asked for my number and we stood in the corner talking for about 3 hours. After midnight, some folks decided to leave or head out to the bars. As I was trying to decide what to do, I got a text from Nathan: “Don’t leave.” Message received. Seems like S might be right after all.

After people cleared out of the apartment, Nathan had the most clever line: “have you seen my room?” I hadn’t, although I would grow to become familiar with it over the next 9 hours or so.

Fast forward through some life chatting and a few heavy make-out sessions, Nathan told me to get into his bed, while he briefly excused himself. Just enough time for me to text S: “I’m not coming home tonight.” and my high school BFF, Jaclyn, “Is it too soon to go home with someone else?” except we all know that at this point, her answer didn’t matter.

Nate turned out to be exactly what I needed that night. With mood lighting and a perfectly curated playlist, this was obviously not his first rodeo, and 4 hours and 3 orgasms on my end, we fell into a blissful slumber. At one point his roommate walked in to ask if he could bang Nathan’s best friend from high school and told us we had great form.


I woke up before he did and wondered if I should sneak out. This was my first ever one night stand. What was the proper etiquette for the morning after? I decided that leaving was probably best. I went to the bathroom and went back to his room to get my bag (rookie mistake!) and ended up waking him up. But he was a gentleman, suggested I get back into bed, got me water and we talked, snuggled and laughed, until the sun was too high in the sky. He walked me to the door and left me with a kiss and one of the more ridiculous nights of my life.

As I snapchatted S and Jaclyn from my “cab ride o shame,” I couldn’t help but smile at myself. I had put myself out there and had a really awesome experience because of it. I tried to repeat the experience the following weekend: “Hey, down for a repeat of last Friday night?” but he responded with something about how the rain would mess up drinking on the roof. He was either not picking up what I was putting down or blowing me off, so I decided to pick up my pride and continue on my adventure of dating in NYC.

At least the experience of going on my first date was over, right? Until all of my friends very clearly reminded me I hadn’t actually gone on a date. Was I ready for the awkward first drink or conversation over coffee? What if there was no connection? Only one way to find out…



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