The Tinder Date That Inspired Me To Quit My Job And Move Across The Country

It was a typical Saturday afternoon, May 9, 2015 to be exact. I was hungover as shit FaceTiming a guy I had literally picked up on the streets of Manhattan a month prior. He lived back in Massachusetts and briefly mentioned that he would be in Boston that night.

I packed a bag and decided to explore Central Park. New York was all I've ever known. I've lived there my entire life and after residing on the Upper West Side for the last year, I started to feel suffocated. While wandering the park, I decided to make friends and ask them more about their life stories.

Sitting on a rock, I called my mother and told her that I was going to book a one-way Megabus ticket from NYC to Boston. I lied and told her I had a place to stay. I mean, theoretically I knew someone who lived there that I met the previous summer for about 10 minutes at a WeWork Camp, but I hadn't spoken to him since.

“You know I never care too much about what you do. Do whatever you want. Do whatever makes your hair blow back. Just don't let me find out,” she said.

I hung up the phone, smiled and headed back to my apartment to shower and buy a ticket. It was 3:10 pm when I arrived home, and the next bus would depart at 4:20 pm. Without hesitation, I purchased a ticket, packed my bag and rushed to the bus stop. I made it with minutes to spare.

When I arrived in Boston, I was on a mission to find mozzarella sticks. With no luck, I found myself at a cute Mexican restaurant.

“Do you guys have a section for single people,” I humorously asked the waitress. She led me to the bar where I saw a young attractive man sitting alone.

“Is this seat taken?” I asked. “It is now,” he replied. “What are you doing tonight?” I asked.

His name was Chad and he was also in town alone. After talking over a drink, we agreed to drop my bag off at his hotel and hit the town together. He was from the UK and never had a shot of Fireball before. I guess it's not as decorated overseas as it is here in America.

I bought him his first shot of Fireball and the night took flight. At the end of the night, we opened the door for a couple getting out of a taxi. We started to get inside of the cab when the couple invited us for drinks on the rooftop of their apartment. We couldn't resist.

I couldn't remember the last time I had seen a city skyline that wasn't NYC. I felt so alive as we talked and danced on their rooftop.(I hope the couple who welcomed us sees this; thank you so much!)

We went back to the hotel around 4 am and played around in bed. Unfortunately neither of us had a condom, so we went to bed shortly after.

The next day at brunch, we called my mother on speaker to wish her a happy Mother's Day. I told her about my adventures and how we met. My mother giggled and told me to enjoy myself. She was having a blast picking tomatoes in our backyard.

We went our separate ways after brunch and I headed to a nearby park. Looking to continue my adventures, I figured the only place to find people to hangout with on Mother's Day would be Tinder. I re-downloaded the app and swiped right 100 times.

Shortly after, I found myself having mimosas with one of my other Tinder matches. He was hungover and had some time to spare before a family party. We talked about life, made jokes and I laughed so hard I snorted. Snot flew all over my face. He told me that if I were anyone else, he would have left. But we were having such a good time and it was hilarious to him. I didn't even flinch through it all.

My date took me sight seeing around Boston and eventually headed off to a family party. I found myself at the Boston Commons, where I opened Tinder and swiped right 100 times again. I matched with a dorky looking guy name William. We instantly agreed to meet up.

As we approached each other, I couldn't help but smile. He was unbelievably sexier than his profile led me to believe and his personality was so genuine. We connected instantly over froyo.

After our date, he kissed me and it was magical. My hat fell on the floor and butterflies filled my stomach. For once in my life I imagined living in another city. It scared the living sh*t out of me. Being that it was Mother's Day, he too went to a family party to attend. We agreed to meet up afterward.

I had this heartbreaking feeling that I wouldn't see him again, or that night at least. It was a Sunday and I had to catch the 2 am bus back to NYC to make it home in time for a 7 am sales meeting. I headed to the closest bar to catch up on some work over a drink while I waited for William.

As I acknowledged the fact that I was getting stood up, a man approached me at the bar, curious as to what I had been working on so diligently at a bar by myself. I explained my trip to him and how I was killing time before my bus back to NYC. He kindly welcomed me to drink with both him and his friend.

We were having a blast when they offered me a place to stay, no strings attached. I could tell they were genuine. We drank and danced the night away until I wrote my 7 am meeting off as a dead loss. This was very unusual of me.

I woke up at 10 am in a beautiful two-story hotel room. It was the nicest thing I had ever seen. Both of the guys had to leave early for work and told me to enjoy myself in the hotel room.

As I took a bunch of selfies and photos to show my friends, William texted me, apologizing about the previous night. I didn't care; I still wanted to see him. I packed my bag and headed toward his apartment. We met up and had a blast. I felt so connected to him. Not because I wanted to date him, but something about him inspired me. Something about me had changed. I didn't want to go back to the city I had dreamt of living in my entire life.

As the time approached for me to leave and catch my 5 pm bus back to NYC, I was overwhelmed with sadness. I wondered what the f*ck I was going to do with myself back in NYC.

Needless to say, I didn't catch the 5 pm bus back to New York. I ended up going on one last date with the cofounder of a tech startup in Boston, pushing my bus back one last time to 2 am Tuesday morning.

I arrived in New York City at 7 am Tuesday, walked to my office and showered in our gym. My mind was full of confusion as I tried my best to push through the workday. I left my office at 5 pm on the dot, and walked home wondering what the best next steps would be.

The next day, I had an open conversation with my manager. Over the previous months I had expressed feeling depressed and unwelcome at work. We all knew the solution for a while, this trip just gave me the balls to admit it.

On May 13, I left an amazing job, packed a bag and two weeks later I began my backpacking adventure from NYC to LA.

Don't fret; I'll share more about that adventure in another post.