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When to End a Friendship and How to Do It

The wrong friend can cause us enormous harm.

Imagine that you have had a dear friend for the better part of your life. This person has been through it all with you—the good, the bad, the ugly, and the beautiful. You’d say of this person that they’ve made you a better person, challenging you to stretch yourself and supporting you no matter what. Now imagine that you and that friend have grown apart; your interests and commitments have changed, as has theirs. Perhaps your interests and commitments have become not just distinct but opposed. You find yourself at a crossroads—do you end the friendship? Do you break up with them?

While there are yards of books exploring the “to end or not to end” question of romantic relationships, resources are scarce when it comes to friendship. This may be in part a consequence of the fact that friendships are often relegated to second-tier status in people's lives. Romantic partners and families come first; friends get what is left over. The expression “just a friend” cements the second-class status of friendships. Yet they do matter enormously—as we realize when we are about to lose them.

The great Roman philosopher/orator/politician Cicero (106-43 BCE) understood the importance of friendships and the role and place the right sort of friend should occupy in life. Friendship played a different role in Cicero’s life than it does for most people today. Drawing from the work of Aristotle, Cicero regarded friendship as the most important relationship a man could have. The quality of person mattered enormously; Cicero argues for choosing friends who have the right sort of good character because such people help to make others better people. The right friend becomes a second self.

And now here you are thinking of casting off your second self. It is a momentous decision, because you do lose a part of yourself.

Cicero contends that there are cases in which a person is justified and perhaps even required to end a friendship in order to preserve their own character. He offers a general rule: Neither ask nor consent to do what is wrong. A genuine friend would not want you to compromise your integrity and most certainly would not want to be the cause of your doing so. The issue is what counts as "wrong." Cicero offers some types of cases I will make more concrete and particular. He uses the world “immoral” and his use is really quite ordinary: Something immoral goes against a set of shared values and commitments. Going against those values and commitments is what makes an act wrong.

  • Your friend makes an immoral request of you. It may start with request to tell a little white lie or to to shade the truth about a relatively minor issue. Subsequent requests may be for bigger and bigger lies.
  • Your friend wants you to pander to his immoral desires. “Pander” is the crucial word here; they want you not just to go along grudgingly with their desires but to cater to those desires. Even more, they may want you to have and act on those desires yourself.
  • Your friend asks you to inflict a wrong on another person. Again, this may start with something small and inconsequential. The issue is that your friend is getting you to do their dirty work.
  • Your friend’s vicious conduct affects others—yourself or a total stranger. “Vicious” is beyond mean; it is reprehensible and perhaps even unforgivable. A person with good moral character cannot ignore this sort of act; it demands action.

It is a form of extortion when a friend cloaks their request as being “for the sake of our friendship.” It is even worse when the friend punishes you in some way for not doing what they want. You may feel trapped and deeply torn at the same time.

Now you recognize you need to end the friendship. But how to do that? It is easy to avoid or even “ghost” acquaintances but not so with a person who has been at the center of your social and familial life. How do you resign a friendship? Cicero is helpful here too.

Whenever possible, he counsels:

  • Allow a friendship to die out gradually through reducing social interaction. Cicero says this is more like unstitching something versus tearing it apart.
  • Avoid enmity. Don’t become overtly hostile and aggressive by antagonizing. Here the concern is to protect your character: You don’t want to start acting in ways that are harmful or immoral or vicious.
  • Do not enlist other friends in this undertaking. In the same way it was wrong for your friend to ask you to do their dirty work, it is wrong to have your other friends do your work in ending the friendship. Friends may support you in this undertaking, but they cannot do it for you.

There will be instances when a friendship needs to end immediately. The best course of action is to end it in a way that avoids hostility and the enlistment of other friends. Your friend may try to manipulate and punish you in many of the same ways they did earlier, but with greater force. Your friend may never understand why you are doing what you recognize you must do.

Cicero describes reaching the point at which a friendship must end as a disaster. It is a disaster because it comes with great loss, chaos, uncertainty, and grief. But it may be exactly the thing you must do to preserve your character.

Note: I am using “they” and “their” in order to be more gender inclusive.

Facebook image: Antonio Guilem/Shutterstock


Cicero, Marcus Tullius. "Laelius de Amicitia."