• Mica Montana Gray

Of chess games, saying no + setting boundaries in dating

Updated: Jun 21

*post migrated from medium*


I like to play chess. I do, I enjoy it. I’m not the best at it, but I know my way around a board. I had started playing a couple of years ago. Sometime in 2019 I realised that I often didn’t win when I played as I hardly ever played to win. I always played for the sake of playing, afraid to make certain moves because I expected that I would fail. I realised that was how I was approaching things in my life too, never really putting the effort in to be successful, always making defensive moves so that I could avoid disappointment. Of course, that only led to more disappointment.


I started trying a bit more and I actually started winning the chess games I played. Turns out, the effort was worth it. Now when I approach situations in other areas of my life, for example my career, I remember that lesson, that I can play to win and it motivates me. I’ve never applied the chess analogy to relationships however, as people’s feelings are not a game and in relationships there is nothing to ‘win’. However, a couple of weeks ago I definitely felt like a chess piece caught in a trap.


I was flowing through a general conversation with a guy I was exploring relationship with before the conversation came to a halt. He asked me to share a particular story and I expressed that I wasn’t entirely comfortable because I didn’t know him that well and it felt inappropriate. He however, was curious and seemed unwilling to take that as an answer. He asked me how it was inappropriate to share this story within a friendship and I saw the space between us morph into a chess board.


I surveyed the board and went through all of the possible moves I could make. I could go left and admit that it wasn’t actually inappropriate because I’d shared it with other friends, but that meant that he would then be in a position to ask whether we are friends, in which case my move would be to say yes and I’d have to explain why there’s a different rule for him and others — or I would be in a position where I’d have to say no and deny our friendship and put myself at risk of losing the whole game. I could go right and keep asserting that it was inappropriate, but that might make his next move defensive and would mean that we wouldn’t move forward across the board. I could go forwards and explain what the real crux of the issue was — the fact that our relationship was uncertain. I wasn’t sure if we were friends or more and therefore I wasn’t sure what was safe to share and what wasn’t. That didn’t seem desirable to me either because that would have left me open to being taken out by vulnerability. I started to feel trapped. I had nowhere to move. The pressure kicked in as it does when you’re playing chess and I thought damn, I will just have to move. I’ll move forward and just take the L.


I moved forward and told the truth. I explained why it was inappropriate, why I felt uncomfortable sharing. In the process of explaining however, I felt a sense of freedom and decided to make the additional move of removing the boundary and sharing the story I was initially trying to avoid — because he was right, what was the harm?


The harm showed itself as we continued the conversation. I noticed that I felt disappointed in myself and annoyed at him, and it was starting to show. I wondered why I was acting how I was and looking through the chess board view, I realised I was annoyed at myself because I had given up my chess piece for no reason at all and I was annoyed at him because I felt that he had made me. In actual reality however, I hadn’t been trapped at all. Unless there is a literal gun to my head I’m never trapped. There were plenty of moves I could have made and even if there wasn’t, I could have walked away from the table altogether. I was so angry with myself for not seeing any of that in the moment. ‘I’m smarter than to fall for this!’ one of my internal voices kept saying.


I could have reasserted the boundary but instead I had felt pressured by his initial challenge to it. I had asked myself as I told myself to do, whether I was happy to share the story and, in the end, I felt that I was — but I wasn’t being honest with myself. That was my first oversight, to not realise that I was responding out of pressure and not freedom. The truth of it is that I wasn’t okay with it at all. I just wanted to be because he seemed to want me to be. The other mistake I had made, was to assume that I knew the moves that he would make if I did assert the boundary. I have played enough chess games to know that people often do things to surprise you.


After realising this, I went back and asked if I could reflect on our conversation out loud so that I could process all of this. He said yes. I brought to recollection what had happened in our conversation. I explored how that conversation led to the feelings I was having, how it could’ve gone differently, how he could have/should have respected the boundary rather than pushing at it. He heard me and engaged in his own reflection.


I also reflected a bit more on my own actions. Why did I suddenly decide that it was okay for me to drop the boundary I had originally asserted? I only reassessed the boundary in that moment because he had challenged it, not because I genuinely thought it needed to be reassessed. Boundaries are meant to act as walls and not gates, they are supposed to facilitate movement of things, so there is a time to open the gates up to let things move in or out, however that time isn’t you’re your boundary is under pressure at 2am and it’s too dark to see what’s really going on.


What was really going on was that I felt he would be unhappy with me if I pushed back. What was really going on was that I felt that I had to believe it was ‘not that deep’ to share so he would think I was cool and know that I was ‘free’, and so that I could see myself in the same way. What was happening was, that I felt like the boundary was acting as a barrier to our relationship, when it wasn’t at all and I was annoyed at him because I felt he had made me feel like that. I felt he had won one over on me and that what I now had to do was win one over on him. In actuality, where I felt the boundary was acting as a barrier, to reassert it would have actually helped to preserve the relationship as I would have avoided acting out my annoyance. It made me realise how important boundaries are to maintain healthy relationships.


I was proud at myself however, for not letting myself just sit in my feelings of disappointment and self-betrayal. I went and had a conversation about it and shared how I was feeling. That felt vulnerable, but the whole situation in itself was vulnerable. I was happy that we were able to have the conversation and that it opened the door to the clarity I needed to define our relationship. At the end of it I felt so much peace and freedom in my soul and I was happy, because looking through the chess view, somehow, we’d both moved forward across the board. Neither of us had made defensive moves.


It reminded me that sometimes, it’s not the mistake you make but what you do after you’ve made it. As much as I had felt I had betrayed myself, I went back to learn about what had happened, I went to talk about it too so that I could check my assumption of him trying to play me, so that next time I’ll know that if I find myself in a similar situation again I’ll know that it is safe to reassert the boundary, I’ll know there’s actually space to breathe when I feel pressured, that I can actually just choose to just go to sleep if I need to. I’ll remember that I’m never trapped in a situation or a conversation. And even if I do fall into that again, I’ll know that if I take some time to learn through it afterwards I’ll come into deeper relationship with myself. That’s the real win.

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