Why My Dating Experiences End Poorly & What I've Learned from Them 

Dating is all about perspective and a journey of self-discovery

Valentine's Day is often portrayed as the most romantic day of the year. It’s supposed to be a day to celebrate love and show appreciation for your significant other, but what about for those who don't have a partner or who have just gone through a breakup?  

My dating life has been a . . . turbulent experience to say the least.  

Since May 2022, I’ve dated, or at least been on dates with, five men. Some of them were real heart breakers, some of them ended mutually, some of them I still feel like they were “the one that got away” (cue Katy Perry on Apple Music).  

I will not discredit the pain that I have endured with some of them, nor will I discredit how happy others made me. Neither outweigh the other, nor were some more meaningful than others. As cliché as it sounds, each dating encounter was a learning experience and it made me stronger, even if it didn’t feel like it at the time. It pushed me onto a new path and has helped me on the path to self-discovery. 

You might be sitting there thinking, “okay, so this guy is trauma dumping for his benefit,” but I would politely disagree. I am trauma dumping hopefully for your benefit. The through line of dating experience is that I learned so much about myself. I’ve learned what I like and what I dislike in relationships and the infamous situationship. I’ve learned about the types of people I thrive with and I’ve learned about the types of people who I don’t necessarily jive with. I’ve been able to form strong bonds, but they didn’t always necessarily last. Every experience — and every man — was unique, different from the last.  

In May 2022, I got out of my second long-term relationship with someone who I adored. I remember the exact date because it happened on the only Friday the 13 in 2022 (go figure something bad would happen on that day). We just went on a ghost walk at the Hermitage Ruins (which by the way, if you haven’t been, definitely check it out because it’s SO creepy). The entire night I could tell something was off and when we got home later that night, I knew a breakup was imminent (maybe I’m a psychic?). Now that it’s been almost a year, I like to joke and say that it was the spirits playing tricks on me. 

The relationship was largely long distance, with spurts of in-person periods throughout the school year. While that took a bit of a toll on me, I think I became comfortable not always seeing someone. I recognized that space is important. Now, that doesn’t mean that I didn’t always want to see him, but I was okay knowing that there would be many times I couldn’t. That’s what happens when two people live two busy lives. I have remained very close friends with this person and I wouldn’t have changed a single thing about the time we spent together. Yes, we both made some mistakes, but we’re both human. I’ve forgiven myself for those mistakes and I’m grateful I got to keep the benefits of having this person in my life.  

Over the summer of 2022, I took some time for myself and went back home, since that’s the one place where I feel I can have my guard down and focus. I took the time to focus on my health, shedding 30 pounds of what I had deemed my “relationship weight”, focused on my passions, hobbies and relearned what it meant to support myself. I had a lot of support from the established people in my life, but also others who were new. Many of my new work colleagues were quick to offer advice, support or their ear to what I was going through — and to those individuals, I will always be grateful for that. 

I eventually redownloaded the typical dating apps and started to explore who was out there. The first person who I instantly connected moved from England literally a few weeks before we started talking. I was smitten even though he wasn’t a monarchist. Things were going well, until he told me that he didn’t want a relationship. I was a little hurt because I felt a tad led on, but I didn’t blame him — he was trying to start his life in Toronto, why would he want to be tied down so early on? He was the first guy I really had spoken to since my last long-term relationship and I learned what it was like to start dating again.  

Next was someone who I had spoken to at the beginning of COVID who I matched with online. We reconnected and went on a couple dates. Things didn’t necessarily end, but more or less fizzled out. I’m not really sure if there was a lesson associated with this, but it was nice to reconnect with someone who I genuinely admire.  

Around October 2022, I got a message on a dating app from another person, who I thought was interesting. He somehow felt different than the men I dated in the past, so I was intrigued. We went on a few dates, but he told me that he wasn’t really looking for anything at the moment. By that point, that phrase kind of took a toll on my mental health. Why was nobody wanting to pursue something with me? It took a lot of reflection to realize that it wasn’t me, rather just the situations I kept finding myself in. 

One day in November, I was scrolling through Instagram and I came across someone who I had a crush on since my second-year. I decided to shoot my shot and message him. To my surprise, he messaged back and we ended up dating for a month and a half. I don’t think I felt as infatuated with someone since my long-term relationship. I would also confidently say that I had some of the best dates I’ve ever been on were with him. Unfortunately, this one also didn’t work out. Although it wasn’t a break up because we weren’t officially in a relationship, it sure as hell felt like one. Let me tell you, it was HARD at some points. In hindsight, I realized that I wasn’t really ready for a relationship either.  

Around the same time we started dating, I started therapy for the second time in my life. I was feeling incredibly anxious in all aspects of my life and I know constantly hearing the line “I don’t want a relationship right now but you’re a really great guy” was triggering for me. As ironic as it was, his reason for ending things was also how I was feeling for a while. After talking things over with my mother and my therapist, I came to the realization that I felt my chapter in Hamilton was also nearing its end.  

I have some regrets about this one. I let some of the interactions with the previous men I dated shape how I perceived the actions of this boy. My past with men not wanting a relationship bled into my present, which caused me to doubt both of our actions and created a self-fulfilling prophecy. With that said, I’m so happy I pushed myself outside of my comfort zone and slid into his DMs. It was an absolute pleasure getting to know this individual for the month and a half we dated and for the little bit we talked after. While I’m sad that we couldn’t be friends in the end, it taught me a valuable lesson. Just because things started off great, doesn’t mean they are always going to work out in the end. That’s okay and doesn’t have to be a bad thing. I learned a lot with this one and I will always be thankful for those shared experiences. 

And here we are now, February 2023. I’ve once again reconnected with someone who I talked to at the start of the pandemic and we’ve hung out a few times. I’ve also applied to some Master’s programs outside of Hamilton so I can gain new experiences and start my next chapter. I’ve continued therapy and have questioned what is in my control and outside of my control. Rethinking many of the stresses and anxieties in my life through this lens have immensely reshaped my mental and emotional state for the better. I’m once again relearning who I am and what I want both out of life and in a relationship context. I don’t think I’m ready for a long-term relationship, nor do I want one at the moment. I want to focus on myself, maybe go on some dates and meet new people along the way. I would not have come to these realizations if it wasn’t for every single person I dated over the last year. There were a couple in particular who especially shaped my trajectory and they know who they are.  

I wouldn’t say that things ended overtly well with anybody, but it is all a matter of perspective. Of course, hindsight is 20-20 but I’m not the kind of guy to be bitter about things ending. I strive to end things amicably to seek closure. Reshaping my perspectives on what I initially perceived as “bad dating experiences” and shifting them to learning experiences helped me find that closure.  

My hope after reading this article is that if you are in a slump about your dating life — whether you’re queer, straight or anything in between or outside — that you take the time you need to self-reflect and question why you are feeling the way you are. What I want you to take away is that you are still you and you have just learned so much about the person you are supposed to be in the end. Each person we encounter in our lives helps us self-actualize our own potential. It took me a long time to get myself to that perspective and I don’t think you’ll get there overnight. But hopefully with time, you will be able to reflect on your past experiences with people be able to find some sort of inner peace that for better or for worse, that person has changed your life and made you the incredibly resilient person you are today.