Dating: A Game I No Longer Need To Win

I’ve always approached dating as a game. A game I needed to win. Winning meant getting dates and finding a girlfriend in the short-term. Over the long term, falling in love and getting married. Despite my desire to win, I’ve never actually made it across the finish line. After my last break up led to two severely broken hearts (mine and hers), it became clear that I needed a new approach to the game. I began by looking into my past to devise a new strategy. What I found instead was that I should never have been playing to win in the first place.    

The deep dive into my past revealed that my need to win had created two key behavioral patterns that were the driving force behind all of my heartbreak. (Yes, the irony is thick).  

1. My self-esteem was attached to my relationship status. 

From an early age, I was taught that winning was integral to being a successful person and that being alone was something to be ashamed of. As a result, I became so focused on “winning” the game of dating that I rarely considered if the woman was truly a great match for me. Instead of prioritizing connection, common interests, and shared values, I prioritized looks, financial success, and avoiding loneliness. 

2. I was a terrible ender of relationships. 

Not only did my need to win cause me to get into relationships with women who were not great matches for me, it also caused me to stay in them for far too long. Prior to my most recent heartbreak, I had only cleanly ended one other relationship. And only because I was betrayed. Otherwise, I was so afraid of “losing” aka “being alone” that I would hold onto things well after I knew the woman wasn’t right for me. Communicate my true feelings? I could never.

Fortunately, my subconscious was always there to help make the woman do it for me. Unfortunately, most of my relationships ended either because I cheated or became so distant that my ex had no choice but to end things for us both. 

These were powerful realizations. Embarrassing, but powerful. It was clear that trying to win the game of dating would never work for me. But I still wanted to get married and have a family, so I needed to come up with an alternative approach. Over the last eighteen months, I’ve shifted my dating efforts to learning instead of winning. 

My new new dating mindset is as follows:   

When I first meet a woman, I’m trying to learn her true nature and whether we’re compatible. I also want the woman to learn my true nature.

I’ve implemented this new mindset over the last eighteen months, and it’s produced three great outcomes: 

1. I’ve learned a lot about my dating preferences. 

What are the qualities I need in a partner? What are the qualities I will not accept? I had never answered these questions until recently, opting to fly by the seat of my pants and allowing my emotions to make decisions for me. Instead of worrying about whether a woman likes me enough to go on a second date, I’m evaluating whether going on a second date actually makes sense. 

2. I am more comfortable accepting failure

When I was trying to win at dating, I always proposed first and second date ideas that involved drinking alcohol. Often, I would show up already having had 1-2 drinks. I believed I was more confident and likable when I was slightly intoxicated, giving me the best shot at winning. I’ve since learned that women will eventually learn my true nature anyways, so there is no point in hiding behind alcohol.

I’ve also learned that alcohol changes my perception of people, negatively impacting my ability to learn their true nature. Now, I plan early date ideas that give us both an opportunity to express ourselves: line dancing lessons at a country western club, ice skating at the Olympic Oval, cooking a new meal at home, or coffee at our favorite café.

3. I can end a relationship in a healthy way.

Since I changed my definition of winning, I’ve ended multiple relationships. Because I’m more comfortable with failure, I’m better at determining when someone is not right for me. I’ve become more in touch with my gut, which helps me to avoid ignoring early warning signs. Ending things sooner also saves time for both of us and creates space to make new connections.

Although I am still single, I’ve never had a healthier relationship with dating or myself. My self-confidence is near all-time highs, I’m not afraid to end relationships, and I don’t need to hide my personality behind alcohol. I’d love to find a life partner and start a family, but I no longer need it to be okay.

For the first time in my life I’m happy being alone. I hate that it took so much heartbreak for me to get to this place, but I’m grateful for it nonetheless. Without it, I’d still be trying to win the game!

P.S. - I’d like to dedicate this essay to AG. Thank you for always pushing me to go take risks, and for believing in me.