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50 Dates of Gray

Updated: Jan 22

Finding Compassion In Our Dating Life


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We tend to make dating very black and white. We had a bad date, so now that is a bad person. The relationship didn’t last or the breakup was bad, so now we paint that person as lower than low. But the truth is dating is a lot more of gray area, than it could ever be black or white.


Why? Because we are humans, and humans are multifaceted beings, meaning we have a lot of sides. We all have good times in our lives and low times in our lives. Good days and bad days. Moments we are proud of, and times we hope never to have to think of again. That means we can be a bad partner, or a bad date and not be a bad person.

Take me for example, I’ve not only been on bad dates, I have been a bad date. I have been a bad girlfriend. I have done and said truly awful, silly, or off-putting things. I have made mistakes. But I consider myself a decent person, and now I write about the mistakes that I and others made, in the hopes that others won’t repeat them and go through some of the painful experiences I have. That’s a pretty good intention right? But if you were to ask some of my ex’s…they would have a very different take of whether I was a good person or not.


That’s because we all make mistakes. And the same goes for the human being sitting across the table from you on that date, or the person ending that relationship with you. We all have our own inner work to do, some of us more than others, but we do still all have it. Sometimes that inner work goes undone for a very long time, sometimes we may not even know we have it. Which causes us to operate from a ‘wound space” and that space, that great, gaping hole inside of ourselves, can make us do some very interesting, destructive things. We can drink too much, use drugs, breakup with people in terrible ways, be unfaithful in relationships, steal, lie, cheat. If you can think of a bad behavior, I can think of a wound space to match it. At the end of the day, whatever the behavior, it usually comes from a place of deep hurt, and we all have experienced hurt. We might not have done the exact behavior we are judging the other person for, but we have all been selfish, cruel, resentful, jealous and so on, at some point in our lives. We have all experienced those emotions, so whether we fully understand the behavior, we can at least understand the emotion behind it, and there, that place of understanding, is where we meet someone in the heart of compassion.


Now, with that being said, we can practice the art of compassion, the art of empathy, while still holding our boundaries. We can feel compassion for someone without agreeing to a second date with them. We can understand why our partner is participating in destructive behavior, without staying with them. Humans are not all black and white, we have some good we have some bad, we have some dark and we have some light. Chances are you were able to see at least some of that light in the other person or you never would have begun dating them in the first place. We all have a beautiful light and potential inside of us, but it is our decision whether we acknowledge it and choose it, for better or worse, it’s our decision. Your partner may not be currently choosing that light, maybe they are operating from a deep wound space. Running through life like the Tasmanian Devil, swirling destruction and taking down anyone in their path. Please make sure you are not in that path. You can have deep love and compassion for a person, but not be in the way of their destructive force. You can choose to allow them to do the inner work they need to do, on their terms.


Because at the end of the day, destructive behavior of any kind is not ok. We do not get a free pass to hurt others, simply because we have been hurt ourselves. We may think that what happened to us, is the worst thing that could ever happen, but think about it, I am quite certain that someone else has had a worse experience than you. That Is not to diminish what happened to you, or invalidate your feelings, it is simply to demonstrate the logic, of where would we draw the line? How would we determine who got the free pass and who didn’t? What if you got cheated on but someone else got lied to or stolen from? Or what if someone else got lied to, stolen from and cheated on all in the same relationship. See the problem? There would be no end to the passes and the world would be a truly awful place. So no one gets a free pass. We all have to do our inner work, no matter the experiences, and we have to create our own healing. We get to stitch up our “wound space” one loving stitch at a time, because no one else can do it for us. Others can help us along the way, but ultimately it is our responsibility.


So my final advice, is to find the compassion in your heart for others. Dating and relationship work, is some of the deepest work we can do, and it is one of our most vulnerable spaces. So be gentle with each other. If you have a bad date or a relationship doesn’t go the way you want it to, instead of calling that person “crazy” or an “awful person” try to find the expansive compassion for them that lives in your heart. Hold your boundaries, say no to that offer of reconciliation or that second date, but hold space for them in your heart. Do your part to make the world of dating, and the world in general, a more understanding place, and try to meet them in the heart of compassion.

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