When to call it quits with a friend

Part II in a series on making (and ending) friendships

When to call it quits with a friend. . .

Back in middle school in the Philadelphia suburbs, ending a relationship with a boy was a thing best handled through a third party.

We didn’t have the maturity or skills to have that conversation ourselves. We’d send an emissary, usually a close girlfriend, to deliver the line, “She just wants to be friends.” Then we’d avoid the boy for a week or two—about the length of the relationship itself—until the whole thing was forgotten.

It’s unfortunate we didn’t practice having those tough conversations when we were young. Unlike acne and braces, the need to end relationships with clarity and kindness persists well into adulthood.

The soft fade

Just as making friends can feel a lot like dating (see my September 8, post), extricating ourselves from a friendship that no longer fits can feel as awkward and traumatic as a romantic breakup.

We stop returning texts. Lengthen the time between get-togethers. Stop initiating contact. Hope the other person gets the hint and quietly fades away.

In many ways, we haven’t grown up much at all.

Ghosting can feel easier in the short term, but it leaves an unfinished mess behind. Conflict-resolution facilitator Priya Parker suggests a more intentional approach. In a recent New York Times interview, she advocates “the connected goodbye,” in which you acknowledge the importance of a relationship while recognizing that it has run its course.

She was talking specifically about group connections—book club, a pickleball team or a networking group. Sometimes everyone senses it’s time to move on, but no one wants to be the person who says, I think we’re done here.

Why not acknowledge what the group gave us instead? Four months, a year, five years of shared experiences can be worth celebrating, even when it’s time to make room for something else.

It’s personal. Really personal

One-on-one friendships are trickier.

I walked into that same middle school one day and discovered that the person who had been my closest friend the day before was no longer my friend at all. Her mother had decided we weren’t good for each other and forbade her daughter to hang around with me.

Her mother, as it turned out, was right. But that didn’t make it any easier at twelve or thirteen.

It took me a while to regain my footing and reconnect with friends I had neglected while I was so invested in a friendship that had stopped bringing out the best in either of us.

There are also friendships that are perfect for a particular season of life but aren’t meant to last forever. A roommate freshman year at college. Another mom with children the same age. The one person at work who sees the same absurdity you do.

They don’t need to be lifelong friends to matter; sometimes they are simply the right people for a specific season. And we can be grateful for that.

Other friendships become so close that we start to lose our sense of ourselves apart from the other person.

I felt that way with a close friend through high school and college. As we launched our careers, I began to feel that I wasn’t allowed to evolve—that trying new things or thinking differently somehow meant I wasn’t being myself.

But what if myself was becoming someone different?

Growth vs. betrayal

Outgrowing a friendship isn’t necessarily betrayal. Sometimes it’s growth. We need something different. Or we need the freedom to become a version of ourselves that doesn’t fit someone else’s idea of who we are supposed to be.

Sometimes the reasons for leaving are even more serious: a friend who undermines your confidence, ignores boundaries, breaches your trust or simply doesn’t want what’s best for you.

A dear friend experienced a particularly painful version of this when someone close to her made unfounded accusations about her teenage child. Because the accusation went directly to the teen rather than to the parent, the relationship became toxic.

There was no big blowup. No connected goodbye. Only a sudden breach of trust that couldn’t be repaired.

The friendship had become woven into her family’s life—holidays, vacations, shared friends. Walking away meant losing not just a person but an entire piece of her history.

Learning how to leave

I can get behind Parker’s idea of a ritual for ending a group relationship. A final dinner for the supper club. One last book club meeting. A final pickleball round robin. Far more satisfying than watching a group chat slowly die.

But how do we adapt the connected goodbye to a one-on-one relationship? I’m still not sure I’ve matured enough to pull that off smoothly.

I try to invest deeply in my friendships. I hope my closest friends know how much I love them, and that valued acquaintances know how much they enrich my life.

Maybe the real goal isn’t finding a perfect script for ending things, but learning to honor what was and still accept when a chapter has closed.

And if I haven’t returned your email or text lately . . .

It’s not you. It’s me.

I’m still working on my relationship skills.

Have you ever outgrown a friendship_—or realized that a friendship had outgrown you? I’d love to hear your story. Drop me a note at_ jeanmcaulay@gmail.com or share this piece with someone who might connect with it. I’d be honored if you share my blog via jeanmcaulay.com.