“If it happens, it happens,” I shrugged after my latest Thursday night date. “If it’s not her, it’ll be someone else! It’s New York after all!” I often lined up dates Thursday nights. It was the one school-night I allowed myself to go out. Plus Thursday nights are more lively so I figured there was a better chance of the date going well.
She was nice and fun. I told a few stories over drinks and got some easy laughs. It was a casual date. But nothing memorable. We met up a couple times thereafter in the ensuing weeks, but, like nearly all relationships I had during nearly a decade of being single, it fizzled out.
“If it happens, it happens,” those three words were how advanced my thinking was when it came to dating and relationships. For some reason, I put little effort into intimate relationships. But I had limitless energy to pour into in my academic, athletic and professional careers. I somehow thought I simply deserved a romantic relationship and that it would just happen to me.
At 11 years old, I was cut from the elite hockey team I desperately wanted to be on. I was not a good enough skater I was told. I was devastated. I had expected to be on the elite team. After wallowing in self-pity, I eventually decided that was not going to happen again. Tryouts for the elite team were not for another year, but, in my mind, the hard work for the following year's tryouts started immediately. I continued playing on my existing team with even more determination. To get more practice time, every Wednesday after school my mother drove me to a two-hour hockey skills camp. During spring and summer break, I attended a skating camp. By the time tryouts came for the elite team the following year, I was going to be the hardest working and most determined player with the best stride. They would not be able to cut me again. I was thrilled, but not surprised, when I made the team.
Playing hockey taught me to act on my intentions. Wanting and hoping to make the elite team, as I had done initially, is not enough. I had to work hard at it. I carried these lessons into my academic and professional career. So when I achieved what I set out to do, it was not a surprise to me.
Paradoxically, the lessons learned playing hockey and reinforced in my academic and professional career did not transfer to my personal life. It was as if I held my relationships to a lower standard; they did not require the same hard work. I had just expected a romantic relationship to happen. I am young, educated, athletic, employed (at the time) and handsome enough therefore I deserve a formidable partner. It would just happen. In fact, I had visions of grandeur; she would be a star, a doctor, a model, a business woman, the envy of all men. It did not dawn on me that I had to work hard on myself and the relationship for it to happen. It would not just come to me. I was blinded by entitlement.
There are several reasons why I was single for so long: being single is fun, prioritizing career over relationships and I never had permanence in one place. I have lived in Toronto, Barcelona, London and New York over the last dozen years. Every few years I was picking up and moving on. I also became the ‘single guy’ amongst my friends. At twenty one, I moved to London. A city that I had been to once before and had no close friends living in. Without realizing it at the time, to fit in and make friends, I embellished the ‘single guy’ role. I rallied friends to go out, got us into bars and chatted up women. I regaled friends with my antics. Friends commented “Sammy! I live vicariously through you.” It became my role and part of my identity, which followed me wherever I went. It became expected of me; as if I was a performer. I willingly played the role and strived in it. It made me feel accepted by friends who were older than me.
I left relationships up to chance. What little time I spent thinking about relationships was channeled into how they would hold me back. I certainly was not going to change. Ironically, the largest decision in my life, who I spend time with, I did not think about, yet I analyzed every angle of trivial decisions. I labored over the merits of an investment, weighing the pros and cons and playing out each possible scenario. But I had not applied this discipline and work ethic to thinking about relationships.
My earliest memory of reconsidering my approach to relationships was after having lived in New York for several years questioning “is this it?” I was about thirty and my life plateaued. My experiences became repetitive. One year rolled into the next with no discernible difference. Same job, same friends, same apartment, same vacation and mostly same conversation. There needed to be something else. But I did not know what.
I noticed becoming more distant from family and friends. For over a decade my parents and I had lived in different cities during which I barely spent more than ten days with them over the course of an entire year. I worried about our relationship fraying. That was the first relationship I recall wanting to ‘work’ on. It was not broken, but like anything, it could improve. My approach was simple, call regularly and have something to discuss. Avoid recounting the past week’s events. At the same time, my relationship with my guy friends stagnated. Conversations too frequently dissolved into recounting the same old stories. I still enjoy the hilarity of them, but too much of it is tedious. Little by little, conversations with friends morphed into debates about ideas and life and diving into how we were actually feeling. The deeper conversations propelled my relationship with my friends and parents to grow again. It felt good; there was renewed meaning to the relationships.
Then came all the weddings. One after the other. It was not long before I was the only single guy there. I resented being in a relationship because everyone else is doing it. But your environment shapes your thinking. Intimate relationships became more top-of-mind. I admired a few relationships and others I thought “that’s not for me.”
In 2018, my parents celebrated their 40th wedding anniversary. It was moving to see the outpour of love from friends and impact that their relationship has had on so many people. Somehow in the moment it was as if their decades of hard work, challenges and commitment to one another all became clear to me. They had developed an unbreakable bond. They were totally in sync. It is a pleasure to witness. I was inspired to achieve something similar.
My time alone during my year of mostly solo-travel and self-discovery, allowed me to shift my mindset to listen more to how I was feeling and less to my pragmatic self. It was so foreign to me. I prided myself on how pragmatic and unbiased a decision maker I was. I believed emotions clouded clarity of thought. I vividly recall an encounter from years earlier when a close friend confided in me how much of a toll his breakup was taking on him as we rode our bikes on a warm spring evening along the west-side highway in New York. The woman he had been dating was the source of so much anguish. He oscillated between sheer joy when things were going well with her, to unbearable frustration when they were not. My pragmatic assessment was that the negatives outweighed the positives. “End it. Cut her off. And move on,” was my cold advice. “What else is there to discuss? The decision is simple.” I unemotionally retorted as he continued to pour out his heart to me. After a decade of being single, assessing everything so matter-of-factly and suppressing my emotions, I struggled to empathize with him. We now joke about how useless I had been. Reflecting on that moment, awakened me to how out of touch I had been.
My heart sank reading an email stating that I was being broken up with. I was not surprised. We had been dating for a few months. We were in this weird New York dating middle ground of not quite a couple, but beyond casual dating. But it still stung. It was a shot to my ego. My friends had commented on how physically attractive this woman was. It felt good hearing that. I had something they admired. The heartache turned to frustration and anger when I discovered she had blown me off for another guy. That hurt. My close friends rallied around me with a common refrain “Don’t worry about it. She’s not right for you anyway. You deserve better.” Their hearts and intentions were in the right place; they wanted to support me and did. But they only saw my side of the story. As a friend, the natural reaction is to support one another. Otherwise the friendship can be undermined. What I did not hear, but could not shake from my head was “what did I do to deserve this?” After all, “I’m smart, handsome, athletic and have a good career - yet you don't want to be with me?” I wondered. “How could that be?” I was puzzled.
This was the first time I felt cheated. Usually in relationships that fizzled out I blamed the other person. It was easier to lay blame than to accept that maybe I played a role in things ending. Perhaps it was maturity, frustration or having more time on my hands since I had left my job, but after that breakup I kept wondering what I could have done to deserve what happened? “Could it have been me? Was I partly responsible for how things ended?” I replayed old relationships in my head to assess how I showed up. I recounted the complaints women I dated had about me. I thought through fights and missed opportunities. After a lot of reflecting and awkward conversations I discovered I had several behaviors that hampered my relationships. These three in particular were troublesome:
A few years ago, I started working with career and life coaches. Although I had initially engaged my coach to discuss my career, we kept coming back to relationships. It became clear that my career expectations were misaligned. At the time, my career consumed my life. As a result, it was my main source of fulfillment, gratification and self-worth. Staking all my needs on one endeavor, my career, is like putting all my eggs in one basket; it is unlikely to work. We began to discuss what was missing in my life; meaningful relationships topped the list. I drafted a list for my coach of what I wanted in a relationship and a partner. He practically laughed me out of the room.
“All of this!” he exclaimed. “Are you serious? Do you really think this is realistic? Do you think this person even exists?” I shrugged my shoulders. “And what about you? What are you willing to compromise on? What are you willing to contribute to make this happen?”
I was stumped. I still thought I was somehow owed my list of demands in a partner. I had not thought at all about what I was willing to compromise nor what I would do to earn this ideal relationship.
I redrafted my list and reconsidered it as a guide to what I want to provide to and receive from relationships, especially romantic ones:
“What’s your type?” was a question I was regularly asked. Often by caring friends looking to set me up. “I don’t have a type,” I would flippantly answer. After a bit more prying, I would add “fun, attractive, smart.” Those are the most nondescript adjectives. Who does not want a partner who is fun, attractive and smart? I ended up on countless dates wondering what I was doing there. On the dates themselves, I would be asked what am I looking for? I garbled some philosophical drivel that I thought made me look smart, when I really had no clue what I was talking about. The reality was that I spent more time thinking about where we should have the date than what I wanted out of the date itself.
After meeting enough fun, attractive and smart women I realized that those surface level characteristics alone did not create a deep connection. There needed to be something more. I landed on these four qualities:
And then, like we all do, I started following a cute girl, Anne, on Instagram. To my surprise, she actually followed me back. And then messaged me! It was so out of the norm, I was more than intrigued. I was thrilled! We texted back and forth for months. She continually dropped hilarious one-liners. We debated the merits of articles we both read. It was evident she was passionate about her business and creating. All this and we had never actually met in person or even spoke on the phone.
Our first date, six months after our first text message, was entertainingly awkward. Neither of us knew if we were actually on a date. A spark was lit, but then I whisked off on a three week adventure and only messaged Anne occasionally. We reunited in New York, only for me to take off again. There were moments of brilliance together, as if we were in our own oasis, followed by drawn out periods of drought with little communication. Our relationship was like a beautiful drive through a mountainous old country road at sunset; we could see the breathtaking horizon and glimpses of what the relationship could be, but man was it a bumpy road.
A lot of the bumps in the road were my doing. Although I was now more aware of my destructive relationship behaviors, they kept creeping back in. It is one thing to be aware of it, it is a whole other, much harder thing, to change the behavior. I had learned a lot about myself, but until I had applied the lessons, I had not understood them.
I was still vying for the upper hand. Anne shared how she felt about me. I responded “Thanks. That’s so nice of you, but I’m not sure I can be in a relationship right now.” I had all sorts of excuses why. We lived in different cities. I was working through my transition out of finance and did not want a distraction. She is older than me. She is financially better off than me. (She’ll tell you she’s funnier than me - but I’m an easy laugh) It was not the right time for me. I was focused on why the relationship would not work. “What’s the point of opening up,” I said “if this is going to end anyway.” I even told her I was undateable because of how up in the air my life was. I wanted to step in and out of the relationship when I pleased and assumed everything would be fine. I wanted Anne to be considerate of what I needed, and I would be considerate of what she needed when it suited me. I continued to do things my way. I chose the movie we would watch and the restaurant we went to and when. I would provide unsolicited business advice, which was meant to be helpful, but also had a hint of “look how smart I am.”
It was easier being my old self. I acknowledged my behavior and apologized for it after the fact. It often was not intended, but I still kept doing it.
Thankfully, Anne is incredibly patient. But everyone’s patience runs thin. After a few weeks apart during which our communication was limited to email every other day because Anne was off the grid, things snapped. What started as a manageable disagreement, erupted into a breakup. It was as if I had been looking for a way out to save myself from the inevitable heartache of a breakup and Anne had grown tired of continually putting herself out there and being left hanging.
On a sunny spring afternoon in San Francisco, I put down the phone having just ended things with Anne. Like a broken record skipping a track, my focus suddenly jolted to why the relationship would work instead of why it would not. Helped by two close friends I had been staying with, I realized that Anne embodied what I was looking for and continuing to hide my feelings and emotions would be the death knell of a wonderful relationship. The next day, instead of flying to Toronto as planned, I flew to Washington D.C. and showed up unannounced on Anne’s doorstep.
I had butterflies in my stomach and clammy hands as I rang the doorbell. For the first time, I shared how I felt about her. I nervously stuttered grasping for the right words. I put my feelings out there without knowing how they would be received. I was finally experiencing what it was like to be vulnerable. It is awkward. The uncertainty of how my words would land was unnerving. But it was relieving; like I got a weight off my chest. Together we compromised, I vowed to emote more freely and to be more considerate of what Anne needed. Anne accepted that it was harder for me to articulate my feelings and that she would continue to be patient as I worked through it. The fight was foundational because it proved to each other that we were both willing to work on ourselves and our relationship instead of lamenting on what could have been.
Part of the friction in the early stages of our relationship is that I am slow to love and Anne is not. It takes me a long time to get comfortable with someone, to trust them and to open up. I am not one to fall in love at first sight. Anne is the opposite. She is immediately trusting until she is proven otherwise. Anne knew how she felt about me before I did about her. Both of our approaches are fine. But we could have saved ourselves a few bumps along the road had we been more aware of it and had I been more forthcoming of how I am slow to love instead of leaving Anne guessing about how I felt.
I had been reluctant to jump into a relationship because of my preconceived notions of them. I had viewed relationships as ‘settling down’ and providing ‘security.’ These notions came from cultural norms and were amplified by my own experiences. I have lived a fast paced adventurous life. Settling down did not resonate with me. People joked about being “attached to their ball and chain” and not being able to do something because “the boss does not allow it.” The comments were meant in jest, but there is some truth to it. I feared what these comments joked about; losing my independence. I am supportive of compromise and making decisions in terms of we and not me. But that cannot come at the cost of suffocating my joie de vivre.
I also associated relationships with security. In our patriarchal culture the man typically provides financial security. Often in past relationships, it was on me to provide the security. I was usually the one paying. I would be providing emotional support. Granted, I often earned more than who I was with, did not voice my displeasure with picking up the tabs and willingly provided emotional support. I grew tired of it. I got the impression that a large part of my contribution to the relationship was providing security. I was fine doing it, but there needed to be more.
In one conversation with Anne, my preconceived notion of settling down and security were obliterated. She too is not interested in settling down and did not seek my security. Not settling down does not mean less of a commitment to one another. Rather, it means a continued commitment to our relationship and individual pursuits. We both equally contribute to the security that our relationship provides to us; it is equitable. With that understanding, I felt free. I could pursue our relationship without foolishly fearing it compromised my independence. All that time, I had been held back unnecessarily. Had I voiced my concern earlier, I could have saved us unnecessary aggravation. Our relationship has been liberating and has amplified my joie de vivre.
“If it happens, it happens.” As it turns out, a lot needs to happen for a relationship to happen. The work is difficult, ugly and awkward. It may seem obvious, but for the longest time, I just expected a relationship to happen. As if I just deserved it. I did no work on myself and relationships. Coming to that realization and doing the work has been rewarding in all forms of relationships, especially mine with Anne. Our relationship works so well because of how we make each other feel. We have shared values that create a deep connection. We are both passionate, curious and goofy team players who seek to share experiences together, grow as individuals and partners, contribute to building something greater than the two of us and be intimate with one another.
The other thing that needs to happen is luck. Somehow, someway, crossing paths requires a lot of luck. Anne and I somehow just managed to be scrolling Instagram at the right time. A minute earlier or a second later, and perhaps we would have never met. But I was selling myself short by not working on myself to be prepared for when paths would cross. Michael Jordan did not just expect to make game winning shots. He worked tirelessly to be able to make the shot so that when luck struck, he was ready. As an eleven year old hockey player, I also worked tirelessly to make the elite team. Expecting to make it, without earning it, and hoping luck was on my side was not going to cut it. Relationships are no different. Whether in one or not, you need to be working on it. Nowadays I hold my shoulders up and tell myself “it’s happening.”
What a year it was travelling the world and experiencing new adventures. Breaking away from my prior life. Beyond what I actually did, what did I learn? What life lessons did I take away from my year of reflection that can serve me going forward?
I had been single for a decade. “If it happens, it happens” I thought about relationships. I rarely did any work on myself to be a better partner. I delve into how I held relationships to a lower standard than other aspects of my life. I expose my behaviors that stymied relationships. I finally articulate what it is that I was looking for. What the root cause of my fear of settling down was. And why it was still so hard to change even once I knew all these things.