While the below are written in the context of friendships, they apply to all relationships as well.

1) When the friendship is causing you more anguish than joy

Do you have any friendships which seem to be causing more unhappiness than happiness? We form friendships with others to support each other to become better persons. When the friendship you are in is causing you more anguish than joy, it defeats the purpose why you are even in the friendship to begin with. Unfortunately, most people stay on in negative relationships, causing themselves lots of unhappiness in the process. If you have friendships which are causing you more pain than joy, it might be time to evaluate whether it’s worth it to hold on to them.

2) When he/she is putting in little to no effort in the relationship.

This wasn’t applicable for my situation, but there are times when dynamics of the friendship is lopsided. Say, when one person is putting in more effort than the other person. Such a situation tells you a lot about how much (or little) the friendship means to him/her. As the saying goes – It takes two hands to clap. Without the other person giving the friendship the same attention and priority to this as you are, things can never work out. Sooner than later, you’ll find yourself bending over backwards to keep this friendship afloat. In this case, the best form of respect you can give to yourself is to let the friendship go. If the other person doesn’t value this in the same way, it is pointless to continue on.

3) When the same situation/issue keeps recurring even though you tried addressing it

Where there are obstacles in the friendship, you should first try to sort out these issues with your friend. However, there may come a time when issues remain unresolved despite that. Maybe the friend doesn’t care enough about the friendship (factor #2 above). Maybe both of you are not willing to compromise. Maybe the differences are too huge to be worked out.

Whatever the reasons are, there comes a point where you have to acknowledge that these issues might very well be irreconcilable. You can continue to try to resolve them, but if they could be resolved, they would have been addressed right at the on-start. While you can pour your heart and soul into making things work out, in the long run you become a slave to the relationship.

4) When your fundamental values and beliefs are different

For any friendship or relationship to work out, there has to be certain similarity in fundamental values. Similarity in these values are the big rocks which will hold the friendship in place. Even if other things are dissimilar, the big rocks will enable the friendship to weather through even the toughest storms ahead.

On the other hand, if the core values are fundamentally different, it doesn’t matter even if everything else is same. The journey to keep the relationship together will only become an uphill battle. It’s just like trying to hold the soil of the ground together in a heavy rain. Without the roots of the tree to hold this soil together, everything will just slip away against your best efforts.

For me and K, our friendship started off where we were similar in our consciousness. As I grew through the years, our fundamental philosophies no longer fit. From there, it was either we compromise on our personal growth, or we part ways to embrace our real life paths. We went for the latter.

I believe the most important thing in life is to first be true to ourselves. While conformance has its merits, it should never be done at the expense of our own growth or our values. Compromising on your personal values just to keep a friendship afloat will ultimately only make you miserable. What’s worse, because your true self is repressed, you start to wrap your identity around the friendship. This was what happened to K, which was why we had to let go of the relationship partly so he could grow into his own. You need to first be true to who you are before any meaningful relationship can be formed.

5) When the friendship is preventing either of you from growing as individuals

A friendship is ultimately a third entity formed due to two individuals. Every friendship evolves based on how both parties are growing. Sometimes both parties grow at the same pace. There are times where the friendship is one of stagnancy, where both parties don’t grow. Then there are times when one outgrows the other, by a large margin.

When this happens, you have two options (i) change the dynamics of the friendship to fit this new development, or change yourself to maintain the same dynamics. As I shared in Factor #4, it’s most important to first be true to ourselves. Determine who you are and who you want to be, then decide if this friendship is one that is compatible with you. A friendship that hinders you from growing into your own isn’t the best one for you. On top of that, if you are not able to grow into your own, chances are your friend is facing a similar blockage as well. A real friendship should be one that enables you in your personal life journey, so you can then enable your friend and others in their life journeys as well.

Moving Forward

As all of us evolve in our own personal journeys, we will cross paths with many different people. Some will be just a brief encounter. Some will stay for a while, then leave when the intent of the encounter is served. Some will stay for an extended period of time. Remember that physical friendships may be temporary, but the connection we have towards one another is eternal. Because of that, always ensure the friendships you are in are the ones which are enabling you in your life path. If the friendship is not enabling either party, the best way forward is to let it go. Perhaps one day, when you guys are at a different, better place in life, you might just cross paths again. This time, both of you will be able to connect with each other on a whole different capacity altogether, leading to a different level of connection altogether. "

http://celestinechua.com/blog/2010/01/why-i-parted-ways-with-my-best-friend-of-10-years/