When Life, Love & Travel Don’t Go as Planned

At the beginning of 2018, I decided my motto would be “catch flights, not feelings.” I was ready to travel and experience as much as possible, without tying myself down to any one person. I got half of the equation right (I hopped on 20+ flights over the course of last year), but as far as not catching feelings, I kind of failed miserably (if you consider allowing yourself to be vulnerable a failure, which I don’t).

One thing that’s become very apparent over the past year or two, is that I’m very all or nothing when it comes to sex and romance. I don’t meet that many people that I connect with, so if I’m into you, I’m into you. Even if I know a situation is destined to be casual or fleeting (for example, a fling while travelling), I still feel all the feelings. I don’t think this is necessarily a bad thing (it’s nice to have good feels towards the people you sleep with), it just is what it is.

In May 2018,  I was on a press trip to an adult’s summer camp in Pennsylvania (more on that later) and I met a guy. He was the marketing director for the company sponsoring the camp. We flirted a bit over the weekend, which lead to us making plans to meet up once we were back in New York City (I was in town staying with a friend for the week). This lead to dinner at Miss Lily’s in the East Village, a post dinner kiss at Death & Co, backseat Uber make-outs, a couple of dates & me rushing from his bed on my last morning in NYC to grab my suitcase and head to the airport.

Oh god, did I like this man. He was smart and beautiful and creative. The sex was passionate and connected. I was smitten.

I asked him if he’d like to see me if I came back to visit. He said yes, but in the fall. His son would be staying with him during the summer.

We stayed in touch over the next few months. We sent sexy toe-curling messages back in forth. Sometimes we didn’t speak for a few days. I continued to travel a lot. I went to the Bahamas and Mexico twice. This didn’t feel like other recent flings (there was a guy in Mexico and another in Jamaica). I didn’t date anyone else. I didn’t want to. I kept thinking about our bodies wrapped around each other; his eyes staring into mine the entire time we made love.

It felt special. He felt special.

Fall rolled around and I booked a ticket to New York City. The plan was to stay with the same friend I’d stayed with after camp (we’d become really close the last time I was in town — another piece of my heart I left in New York City).

I was looking forward to hanging with my friend (co-working! drinking wine! vintage shopping!) and spending time with NYC bae, exploring the city hand-in-hand. I was planning on staying a couple of weeks and  seeing what happened.

Almost nothing went according to plan.

Here’s something you should know about me: I don’t cry very often or very easily anymore (thanks, anti-anxiety meds!) but few days into my New York trip, I found myself having a full out emotional meltdown while walking through Times Square. I never thought I’d be the kind of person who’d burst into tears in front of the M&Ms store, but here we were.

(Note: if you’re going to cry in public, do it in Times Square. It’s already kind of awful and it’s so busy that literally no one will care/notice.)

The source of my tears was a culmination of several factors.

Right before I was set to depart, my friend texted me to let me know that she was going to be out of town when I arrived and wouldn’t be able to let me into her apartment (she was abroad visiting family and an elderly relative had passed; prolonging her stay).

There was no way for me to get her keys. I had to find somewhere else to stay at the last minute. I felt weird asking NYC bae if I could stay with him, so the night before I booked an Airbnb (my booking got confirmed a few hours before my flight).

When I got to New York, I learned that NYC bae was also going through some tough family issues. We still had a connection — he held my hand and kissed me on the street and told me it felt like time hadn’t passed at all — but he seemed sadder, quieter and more reserved than he had before. Distracted. Distant.

The dreamy eye-contact was still there. But lying in his bed as he snored next to me, I couldn’t sleep. My mind raced. Was this going anywhere? Had I made a mistake coming here?

My airbnb situation proved to be bad news (turns out sharing a bathroom with strangers isn’t much fun!); my friend still wasn’t back in the city & didn’t have a timeline for when she would be back, and NYC Bae was busy with work and social commitments. Making plans with him felt like pulling teeth.

After a few nights I ditched my sketchy Airbnb and booked myself a room at the Pod 39 Hotel, which turned out to be perfect (I loved this little hotel!) but NYC prices are no joke and it felt like my bank account was bleeding money.

According to scientists, AI can now predict how long your relationship will last, but I’ve always felt the end of love/lust deep in my gut. It’s like a nagging ache that doesn’t go away. It feels like butterflies — the bad kind.

The bad news butterflies were coming in loud and clear. Yet, I was caught in this weird emotional limbo; part of me hoping that the tide would change, while also mourning the likelihood that it wouldn’t.

Throw in the fact that Fall just isn’t my season AT ALL (my seasonal depression is very real) and all felt unexpectedly lonely; like the city of New York was rejecting me; chewing me and spitting me out (which, according to New York transplants, is a very authentic NYC experience).

Since getting treatment for my anxiety, my moods have been really stable. So, to feel this sad in one of the most amazing cities of the world, was kind of scary.

It’s taken me a year to write about this experience, partly because I wasn’t sure how to frame it. I could have glossed over the whole thing and only mentioned the sexy details, but that wouldn’t have been the truth.

The truth is that part of me still feels embarrassed. I wanted so badly for things to work out with NYC bae and for us to build on that little bit of magic we’d had together in the Spring, that I never even considered that it wouldn’t happen. I mean, that’s pretty naive. Especially for someone like me who writes about relationships for a living. I know better than to plan a trip around someone else (without being 100% crystal clear on their intentions) but I did it anyway.

After about 10 days in NYC solo, I was scheduled to go on a press trip to Puerto Vallarta. My friend still hadn’t come back and I was seriously considering changing my flight so I could fly back to Canada directly from Mexico. But, then at the last minute I decided to keep my original ticket and finish out my time in NYC on my own terms.

I’m so glad I did.

When I got back from Mexico, things got better. My friend Gary offered to let me stay at his apartment on the Upper East Side. I stopped waiting around for NYC bae and instead went to a ton of museums. I crossed a few items off my bucket list. I spent time with another girlfriend in town. I also hung out with Gary a bunch and ate lots of good food. Eventually, my friend came back from abroad and we got to hang out, drink wine and dance around her living room to RuPaul.

If you want to find out exactly how I spent my time, make sure to check to check out my post about how to travel to NYC solo in my new travel blog (yes, you read that right!) Love, Peace & Tacos. 

(In the end, NYC bae went out of town while I was in Mexico. We stayed in touch while he was gone, but he didn’t make it back in time before I had to leave the city. At the end of my time in NYC, I flew to St. Lucia for another press trip and then went back to Canada from there.)

I don’t regret going to New York. I also don’t regret any of the feelings I had (even the uncomfortable ones). However, in hindsight I wish I’d been more upfront and asked NYC bae more questions (like, how do you envision our time together in NYC? What will your schedule be like? Do you see this as a fling or something more?) to get a clearer picture of his intentions — before I hopped on a plane.

With that said, life is short. Sometimes you have to take chances to answer questions about the people in your life. I got answers. They weren’t the ones I expected or hoped for, but they were answers nonetheless.

Even though it was uncomfortable, I’m happy I had this experience. It clarified a few things for me — like, I am not destined to be a New Yorker. The city is amazing, but it’s a lot. A wonderful place to visit, but not somewhere I could live longterm. When I got back to the West Coast, I breathed an audible sigh of relief.

Instead of making me bitter, it softened me. It made me realize that I do want to have a partner and to fall in love again. Most importantly, that I can have feelings for someone, they can go away and I’ll get through it. I’ll come out the other side just fine.

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