Dating is Broken Because We Are

Crystal Jackson

There’s this idea that dating is supposed to be fun. I wonder sometimes where that idea comes from. Was it ever fun, really? I look back on my entire history, and I see a lot of unnecessary stress. I see three primary things going on:

  • Me, making assumptions about the person I’m with
  • Me, ignoring red flags
  • Them, changing up on me

Dating is broken because we are.

Think about that. Dating is broken. Because we are. It’s the truth.

Much of the pain I experienced from relationships is because I was a broken, unhealed person trying to connect with people who were at least as damaged. We take all of the pain we haven’t dealt with, and we end up in relationships where we’re still encountering those wounds without healing them.

Instead, we create more injury- in ourselves and in our partners. We’re reactive and triggered by the wounds we won’t address, but we blame our partners for it. It’s a cycle of pain that keeps repeating until we decide to disengage from it to heal ourselves.

The reality is that I was hurting myself by the choices I was making.


When I made assumptions about someone I was dating, I wasn’t dating their authentic selves. I was taking what I wanted and making them fit into that mold. I developed an expectation, and then I was disappointed when they didn’t live up to it. Making assumptions is something we do when we’re broken and looking to get our needs met with anyone rather than the right one.

When we date from a healthy place, we’ll make fewer assumptions. We’ll clarify if we’re unsure rather than choosing to believe what we want to be true. We communicate effectively enough that assumptions don’t play into our relationships.

Red Flags

When I ignored red flags, I was going against my own better judgment and staying in relationships that I already knew wouldn’t work for me in the long run. I would feel disappointed in them when I was really disappointed in myself for ignoring my own intuition.

Ignoring red flags is another thing we do when we haven’t healed our broken places. We know this is bad for us. But we want what we want without counting the cost.

When we begin to grow, evolve, and heal ourselves, we pay attention to our intuition. We keep an eye out for red flags because we’ve learned the lessons and don’t want to repeat the course. We know that ignoring a red flag is not in our best interest.

Their Choices

When they changed up on me, they were the ones with the unhealed wounds. They were the ones who reacted to their own injured places by switching up on me. They weren’t authentic in the first place, so they either revealed who they had been or began to become who they needed to be. It felt like a massive change to me because who I encountered, who they professed to be, wasn’t the truth of them.

When we’re dating people who are in a healthy place, they won’t misrepresent themselves because they know who they are. They’re coming from a secure place. These people aren’t changing up on us because they are who they are from the start. If something does change, they’ll communicate with us about it.


Dating stays broken because too many people keep playing the game when they would be better served to work on their issues. I’ve been guilty of this so many times, and yet I’ve broken the cycle. I took myself out of it- not because I was damaging others but because I wasn’t drawing the right energy toward me in my broken state.

All my matches were a match to my brokenness- not to my healing. I didn’t need someone to fix. I didn’t need to be fixed myself.

I needed to fix myself. I needed to take time to heal and to explore the triggers that trip me up. My neediness. My insecure attachment. My flimsy boundaries. My near-inability to ask for what I need. The soft place in me that is too easily hurt by words too carelessly thrown out.

Dating hasn’t been fun. It’s been a place to go to encounter my own broken places. I could see it reflected back in the damage all around me. I stepped carefully around the wreckage and sat down on the sidelines.

I needed care, real care, and not someone else to make me feel good or act as a distraction from the hurting places. I needed to take the time and space to examine my injuries and to work on healing them. I needed to raise my vibration in order to connect with others who were on the same healing path.

We keep wanting the dating world to fix itself, and we forget we are participants. If we want the broken machine of dating fixed, we have to fix our own damaged parts. We have to be healthy members of the dating community and stop expecting everyone around us to get healed to improve our experience.

Dating is broken because we are, but we don’t have to stay that way. It’s not mandatory to keep dating just because we’re single. We don’t have to keep stumbling across old injuries that make new ones. We don’t have to call our damage “the way we are” and just keep adding to it. We can choose to take responsibility for our own healing.

We need to stop making assumptions and ignoring red flags. We need to take responsibility for knowing who we are well enough that we’re not switching up on someone else when we finally figure it all out. Or stop pretending to be something we’re not.

We need to date from a place of strength and confidence rather than out of a need to be healed by love. Love doesn’t heal us like that. In fact, too often it complicates our healing while wounding others.

We have so many choices. We can keep talking about all the dating trends that have emerged from broken people making poor choices, or we can figure out how to be a changed part of the dating game.

Dating could be fun. I’ve seen it in the movies. I can imagine how that might work. But it can’t work when we’re just broken parts trying to fix ourselves with other broken ones.

I don’t know much about repairing things, but I know it doesn’t work like that.

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Crystal Jackson is a former therapist turned writer. She is the author of the Heart of Madison series and a volume of poetry entitled My Words Are Whiskey. Her work has been featured on Medium, Elite Daily, Thought Catalog, The Good Men Project, and Elephant Journal. When she's not writing, you can find her traveling, paddle boarding, cycling, throwing axes badly but with terrifying enthusiasm, hiking, or curled up with her nose in a book in Madison, Georgia, where she lives with one puppy and two wild and wonderful children. Crystal writes about relationships, mental health, parenting, social justice, and more. Never miss an update. Subscribe to emails:

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