Breaking Up with Friends

A Guide to Saying Goodbye

What in adult life approximates running through a playground and collecting strangers for a game of tag?¹ I’m envious of how easy it has been for each of my daughters. Wondering why making close friendships are so much more difficult after the age of 35 as people “settle down.”

In today's digital age, friendships occur outside of the physical realm. We know, deep down, true friendship is more than a list of names on a screen. It's the shared moments, the mutual understanding, the unspoken pacts and loyalties. Ralph Waldo Emerson wrote in his essay on friendship, "Our intellectual and active powers increase with our affection." They represent worlds within us, worlds that may not have been born until they arrived.

If a friendship straddles the digital and real, unfriending or unfollowing someone isn't just a click of a button—it's a declaration of distance. It's worth considering how ease plays into decisions to terminate friendships. Does the ease of 'unfriending' make it easier to let go, or does the public nature of social media make the process more difficult?

The Hard Thing About Hard Things

Initiating friendships is hard (read up on extraordinary social interactions here). Even harder, what do we do when a friendship starts to fade? When the shared understanding and mutual respect give way to discord and disagreement? When a friendship becomes more draining than fulfilling, it may be time to consider ending it.

I ended a close male friendship in my 30’s. I noticed how much of our time together was him trying to impress me. Thirty, forty minutes could go by after I asked a single question. But it was rarely reciprocated. It wasn’t connection. I was witnessing a drive to achieve social dominance. That said, I wish I told him how I felt. I never clarified that he was chosen among a lot of options. I already respected him. I already cared for him, unconditionally. And yet, he acted like a job interview candidate trapped in amber. I felt unseen in these one-on-one gatherings. Eventually, I stopped and chose others. Where bursty back and forth volleys brought mutual energy and disclosures.

I ended a close male friendship in my 40’s. A tall man, he yelled at my kids for not including his daughter. I could see the fear in their eyes. He didn’t ask them questions. He didn’t listen to their responses. He pounded them down with declarative students of what they should do, what they didn’t do, and how he thinks of them. He didn’t notice that I observed it all from the corner of the room. Shocked, I didn’t say anything until the next day. He apologized profusely and asked to do the same to my kids. But the kids no longer felt safe around him. And when they did see each other again, the initial apology bled into yet another round of blaming my kids. I knew our relationship wouldn’t recover. Did I mention my daughters were under the age of 10? I may have been premature in ending our excursions, embarrassed that I didn’t defend my kids in the moment. Instead, I watched them get berated. It was the last time I served as a quiet bystander.

I ended another close male friendship in my 40’s. He asked for support as he went through a divorce. It was an act of emotional bravery. But I knew them both. So I responded to requests for advice from both of them, asked questions on text to both of them, and offered compassion to both of them. Once, I questioned his decision-making when an elegantly dressed girlfriend accompanied him during a hand off their child. In a crowded sushi restaurant, after 30 minutes of conversation, he halted and said let’s talk. He raised his voice at me, pissed at my dual allegiance. Other diners noticed as I shrunk in my chair while being berated. We disagreed on the defining features of friendship. I will be present and caring but there will be times we disagree. He stood his ground. Our relationship crumbled, collateral damage in an ugly divorce. I still wish it could have survived the turmoil. I do wonder, however, how much displaced rage is tolerable to absorb (especially in public settings).

Ending friendships is a difficult process, a delicate balance of emotions and rationality. But by understanding the strategies available and reflecting on the nature of these relationships, our personality preferences, we can navigate difficult goodbyes with grace and minimal regret.

The Strategies of Friendship Termination

Research has identified three broad approaches for ending undesirable friendships: Gradual Termination, Immediate Termination, and Mediated Termination. But before we jump to termination, let's explore some strategies for attempting to mend cracks.

Strategies for Mending Friendships

1. Flipping the Timing of Apologies: The first step in fixing a dysfunctional friendship is open, honest communication. Express your feelings and concerns in a non-confrontational manner. Use "I" statements to avoid sounding accusatory. Instead of claiming "You never listen to me," say "I feel like my thoughts and feelings aren't being heard." Use what I refer to as the Discomfort Caveat. Begin with an expression of how hard it is to communicate with such intense emotional reactions swirling. For example, say, “I want to tell you something that’s bothering me and I want to apologize in advance because I’m nervous and am unlikely to speak as clearly as desired. I need your friendship. Talking about what’s bothering me might help it last.” By disclosing what you feel, apologizing up front, it’s likely their defensive stance might be lowered a bit. Just enough to welcome a productive disagreement.

2. Setting Boundaries: If your friend is overstepping boundaries, it's important to communicate your limits clearly. Let them know what behavior you find acceptable and what you don't. It's okay to say no and prioritize your own well-being. Even if you are more sensitive than them, even if you have difficulty managing intense emotions, even if your concerns might be viewed as absurd. Discard the social comparisons. If you are bothered and they are interested in your welfare, then a discussion is worthwhile.

3. Seeking Outside Help: If the issues in your friendship are too complex to handle on your own, consider advice from a counselor or therapist or member of your wise friendship council. They can provide guidance and strategies for navigating difficult conversations and resolving conflicts.

4. Taking a Break: Sometimes, a short break can help cool down heated emotions and provide perspective. Use this time to reflect on your friendship and what you want moving forward.

Gradual Termination

As painful as it might be, sometimes a relationship is unfixable or undesirable. Researchers find that when termination is an option, the most preferred strategy is Gradual Termination. This involves slowly reducing the frequency and intensity of contact with the friend until the friendship naturally fades away.

• communication becomes less playful and more formal

• conversation is often limited to special occasions such as birthdays

• hours of availability lessen

• messages are responded to with substantial delays

• fewer active attempts are made to seek them out

It's like a sunset, gradually dimming until the light finally disappears. This strategy is preferred because it minimizes conflict and allows both parties to adjust to the change.

Immediate Termination

On the other end of the spectrum is Immediate Termination. This involves abruptly ending the friendship, often by explicitly telling a friend that it’s over. It's like a band-aid being ripped off – quick, painful, but over in an instant. This is the least preferred strategy, likely due to the potential for conflict and hurt feelings.

Mediated Termination

The third strategy is Mediated Termination. This involves using a third party or indirect means (a letter or email) to end the friendship. It's like sending a messenger to deliver bad news. This strategy helps avoid direct confrontation, but can also feel impersonal or cowardly. Before going this route, give consideration to how much you value courage and seek to exemplify it in social situations.

Think about precedents. If you cannot have a face-to-face conversation or phone call this might not bode well for becoming an assertive person. Decide how important it is to express yourself in a way to get the best possible outcomes for all parties. A skill that is essential for negotiating in relationships, workplaces, car dealerships, and disagreements with refs and parents at sporting events. Make sure to read my prior articles on the power of assertiveness (Part 1 - here and Part 2- here).

Friendship Audit

It can be hard to tell whether you should stay and mend cracks in a friendship or flourish in a relationship elsewhere. Think of a friendship that is experiencing turbulence. Consider five questions:

The Energy Meter: After spending time with your friend, how do you usually feel?

• a) Like I just had a close game of pickleball, full of energy and excitement!

• b) Like I just had a balanced meal, satisfied and content.

• c) Like I just finished a SAT exam, completely drained, exhausted, and deflated.

The Respect Radar: How often does your friend respect your boundaries?

• a) Always, they could lead a seminar on respecting boundaries.

• b) Sometimes, they have moments of forgetfulness.

• c) Rarely, they seem to think boundaries are just a suggestion.

The Validation Vacuum: How often do you feel heard and validated in your friendship?

• a) Always, they're my personal cheerleader.

• b) Sometimes, they have good and bad days.

• c) Rarely, I often feel like I'm talking to a potato.

The Conflict Compass: How do you resolve conflicts in your friendship?

• a) We talk it out and find a solution, like Sherlock and Watson solving a case.

• b) We ignore it and hope it goes away, like a forgotten hoagie in the fridge.

• c) We argue and hold grudges, like a storyline thread through 9 seasons of a soap opera.

The Wellness Barometer: How does this friendship affect your mental health?

• a) Positively, like a constantly available canister of supplemental oxygen to recharge.

• b) It's a mixed bag, often I need a second friend to complain about this friend.

• c) Negatively, they're like an uncomfortable, irritated skin tag that scrapes against my shirt.²

If you answered "C" to most questions, it might be time to consider whether the relationship investment leads to sufficient dividends. Consider the depth and breadth of your existing social network.

Reversal

Old friends are are irreplaceable. They’ve seen us evolve from wide-eyed youth into the adults of today. They are the keepers of secrets, witnesses to stories that cannot be told in polite company, and who can anticipate what disturbs and enthuses us.

They've seen us through first crushes, awkward teenage years, tentative steps into adulthood. They've seen us at our worst, and yet, chose to stick around. They hold up a mirror to our past, reflecting a self that we may have forgotten, but one that shaped us. They ground us, remind us of our roots. It can be hard to discard central characters of early life narrative chapters. Even when we’ve outgrown them, sometimes we keep them for surges of nostalgia. If you do decide to retain these friendships, if problematic, be sure to hold them at a distance for maximal benefits and minimal suffering.

Provocations

Here are a few thought experiments to help you reflect on friendships and how you might handle difficult goodbyes:

1.    Reflect on friendship: Are there any that feel like a never ending chore? What makes these friendships challenging? How do they affect your vitality? Besides identifying draining friendships, understand why they drain you.

2.    Retain flexible options: If you identified a friendship that's more draining than fulfilling, what's your next move? Would you try to improve the relationship first or move straight to termination? If you chose termination, which strategy would you use? Gradual fade, immediate cut-off, or a mediated approach? Sometimes, what seems like an insurmountable problem might just be a bump in the road. So, under what circumstances might it be worth trying to mend a broken friendship? And if we decide to take this path, how can we navigate the process of reconciliation in a way that's respectful and healing for both parties? There's no right or wrong answer. It's about what feels right when you only own half the responsibility.

3.    Explore your personality: How do your personality traits and values influence your approach to friendships? Are you more agreeable and thus more likely to opt for a gradual termination? Or are you more confrontational and inclined towards an immediate termination? Understanding your own preferences helps in navigating difficult decisions effectively.

4.    Imagine the aftermath: How would you feel after ending the friendship? What would you do to cope with the loss? How could you use this experience to foster healthier friendships? Be inclined to learn and grow from social activity that doesn’t align with your identity.

5.    Take action: Now that you've reflected on these questions, it's time to take action. Whether it's having a difficult conversation, setting boundaries, or deciding to part ways, remember that you're doing this for mental health.

Understand that you deserve friendships that bring joy, support, and a sense of belonging. By keeping stock of available strategies and reflecting on default tendencies, we can navigate difficult goodbyes with more grace and less regret. It's okay to prioritize your well-being and let go of relationships that no longer serve you. Be discerning. Spend your finite energy wisely.

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Read Past Issues Here Including:

1. Perhaps the gym. But then I thought of how many people try hard to find a 45 minute window at lunch or during a break from watching the kids. Under time constraints, do you want a stranger to interrupt you with comments on the gym:

“I love this gym — they have the best equipment.”

Will a friendship form when someone asks for help:

”Any tips on how I can build legs that aren’t as gangly as yours?”

Because these are examples of the “proven ways” to start conversations.

2. I am still perseverating about a skin tag I apparently ripped off after having one to five old fashioneds the other night. Yes, it’s disgusting.