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When Breaking Up with Friends Is Hard but Necessary

By Barbara Greenleaf October 19, 2021 Lifestyle

Friendships with women are what get a lot of us through life. On TV, in movies, and on the Net, friendship is exalted and even elevated to the level of one’s “tribe.” But in real life, people can betray confidences, fail to come through when they’re needed most, turn into bores, or are more work than they’re worth.

When our relationships with other women are fulfilling, there’s nothing better. But when we see or speak to others solely out of habit, a sense of duty, or an inability to call it quits, we have a problem.

Friend of Long Standing

Some of us have friends going back to kindergarten. We shared many coming-of-age experiences with them as girls. Then our paths diverged – what with work, husbands, family, philanthropy, and hobbies – and we no longer have anything in common.

Yet we keep up the friendship, feeling too guilty to cut it. It’s as if we owe the relationship something.

Friendships from the Recent Years

Some of us have more recent office friends, PTA friends, bridge friends, or golfing friends with whom we share a common interest. Over time, though, we find that they kick the ball out of the rough when they think no one is looking.

Or they gossip and drag us into it. Or they cheat on their income taxes – and brag about it. Or they engage in petty vendettas. We don’t like to think of ourselves as judgmental, but we all have our values and standards. It’s hard to be friends with people we don’t approve of.

Incompatibility as Friends

Some of us find that certain people just don’t wear well. Maybe we’ve changed or maybe we’ve just run out of patience.

Let’s face it, a lot of people are totally self-absorbed. They exhibit no interest in us but want to tell their own stories, over and over. Tired of being a sounding board for a friend, one woman confided in me, “I feel so used!”

Why Is There a Chasm in the Relationship

If we want to live a considered life – especially now that we are over 60 and we have a heightened awareness that our lives are getting shorter – we may want to take a cold, hard look at why we are dissatisfied with some relationships. Ask yourself:

  • Am I suffering from meaningless “friendship clutter?”
  • Am I seeing certain people out of inertia?
  • Do they manipulate me into saying or doing things I’m not comfortable with?
  • Do I like the person I am when I am with them?

Setting Boundaries

Everyone likes to be embedded in circles of acquaintanceship, so I’m not saying we should cut off anyone who doesn’t meet our exalted standards. If so, we could find ourselves sitting at home alone!

But we don’t have to be wholehearted with everyone, either. In one book on friendship, the author starts out with this question: “If a friend asked you to come over at 3 am and help him bury a body, would you do it?” My first reaction was, “Oh, why couldn’t he ask someone else?” I feel there’s no disgrace in setting boundaries.

How to Break Up With Your Friend

Let’s say you’ve made the decision to end it. Remember the Paul Simon song, “There Must be 50 Ways to Leave your Lover”?

You just slip out the back, Jack
Make a new plan, Stan
You don’t need to be coy, Roy
Just get yourself free
Hop on the bus, Gus
You don’t need to discuss much
Just drop off the key, Lee
And get yourself free

When it comes to friendships, though, there seem to be only three main ways to say goodbye:


Tell the person why you no longer want to be friends. This is extremely unpleasant as chances are she will be hurt and defensive. If you can stand it, this approach has the advantage of getting your grievances off your chest and not allowing any ambiguity that it’s over.


Let the relationship peter out by not answering emails, acting evasive when she wants to set up a Zoom, ignoring her birthday, etc. You continually make excuses and eventually she gets the picture. This morphs into “we just drifted apart.”


This is the middle way. You might have to be in the same orbit at work, church, or play, but you stop giving emotionally. Your interactions become more superficial and less personal. You contrive not to be alone with this person if you can help it.

Socrates said the unexamined life is not worth living. Perhaps it’s time to extend that to “the unfulfilling friendship is not worth having.” Try it out and see where it leads you.

How many close female friends do you have? Have you withdrawn from a friend in the past? Why? How do you feel about that today? Please share your thoughts and stories below.

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The Author

Barbara Greenleaf is the author of the new self-help book, Parents of Adult Children: You Are Not Alone, based on her long-running blog. She has also written a history of childhood and a self-help for working mothers. Barbara was on the staff of The New York Times.

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