During my teens, twenties and thirties, relationships felt like an absolute mystery. Some girls liked me, others didn’t. Some lasted months, some lasted weeks, a few lasted years. But they all ended. Until I found a new one, and walked in with the same hope and optimism yet again. 

Problem was, I learned very little. Usually the reason I thought they ended was the other person was too demanding, didn’t give me enough space, or I stopped liking them. Blame, blame, blame. But that’s all I knew back then. 

Here’s a shortlist of reasons my relationship never worked out. It took quit a bit of reflection, being humbled and self-honesty to get here. 

1. I had no idea what I wanted. 

I entered the relationship with no plan, no goal or any identifiable purpose. I knew I wanted to feel good, that’s about it. I was in it for myself. Now, I was a good guy, I didn’t want to hurt anyone’s feelings, but that’s what always ended up happening. When things were good, I felt good. When conflict came up, I pulled away. I had no overarching goal to support me when the relationship hit  roadblocks.  And when it did, I left. 

2. I gave myself up to get connection

I was so terrified of being left by any of my girlfriends,  I would do almost anything to stay in the relationship (Ironically, I would be the one to leave). True honestly terrified me. I didn’t know how to bring up a conflict in a constructive way. I didn’t even know how to tell someone I was angry with them without being passive-aggressive or slumping into self-pity.  I felt powerless of how to have my back, assert my wants and do it in a way that fostered connection. A showed them a person I thought they wanted me to be, instead of who I was. I was absolutely willing to compromise myself to get a connection, but I could only tolerate it so long. It seemed that leaving the relationship was the only way to get myself back, and predictable, I blamed them in the wreckage. 

3. I had no idea how to handle my emotions

Hell, I didn’t even know I had emotions. I had figured myself to be a pretty even-keel guy. But truthfully, I was so disconnected from my emotions, I had fooled myself that I didn’t have any. One of my favorite authors,  James Hollis writes “A man is largely at the mercy of what he doesn’t know about himself.” And oh boy, was that true for me. I was run by my emotions, but didn’t know it. I would shut-down, blame, feel victimized and pull away form my partner when things become difficult. And when push came to shove, concluded that they must be the ones making me feel this way. I had never learned to sit with myself or tend to my emotional life, and because of that, I essentially forced my partner to be the one to deal with it. Fun. 

4. I didn’t play to win

There are many areas in life where I’m okay with playing not to lose. I don’t need to live next to a beach, even though I’d like to. I don’t need a house with a pool. I don’t need a Dodge Viper in the garage, but it sounds fun. In my opinion, playing not to lose in a relationship is a terrible mistake. And I did it all the time. I was willing to settle for 5/10. I’m not speaking about the women by any means, they were all great people, I’m speaking to the quality of the space between us. I was willing to tolerate feeling disconnected. I was willing to deal with sweeping  problems under the rug. I had created no culture within our relationship about speaking honestly or sharing feedback. So, the relationship felt stagnant after a few months. And, I would tolerate that as well.