No one prepared me for the deep, horrifying pain of breaking up with my best friend. While growing up, I remember hearing adages like, “enjoy it while it lasts”, “you’ll figure out who’s really down for you”, “life-long friendship is rare; you’ll be lucky to end up with one good friend”. I thought it was all very ominous and made me nervous to find out who I’d end up losing. But once it came, I wasn’t surprised, just deeply sad. Nothing extreme or obvious took place; no theft or betrayal. It was just uncomfortable to admit that we had outgrown each other, that we no longer shared a commitment to each other’s well-being or interest in each other’s lives.
As with most things in life, discomfort yields growth. After having endured the initial emotional devastation, I can say with confidence that it was for the best. Living through a friendship breakup has been refined by an ability to discern which friendships to nurture and which to set free. We all have relationships that could take a little TLC, deep cleaning, or reinvestment, however, not every relationship deserves it. Trusting your gut is a good rule of thumb but what happens when the reasons aren’t so obvious? Herein lies 3 questions to help you discern when to hold ‘em when to fold ‘em.
Shasta Nelson, the founder of GirlFriendCircles.com and author of “Frientimacy: How to Deepen Friendships for Lifelong Health and Happiness”, has a simple definition of friendship:
“A friendship is a mutual relationship between two people that is satisfying, safe, and where both people feel seen.”



Hold or Fold Questions: Using Discernment In Friendships
- Does your relationship feel transactional or genuine?
You scratch my back, I’ll scratch yours. The problem with transactional relationships that are predicated on this principle is the constant counting. Counting the number of times you visited them; how many times they texted you back; how many family events you planned; how many times you got them an Uber. All of this is undoubtedly exhausting.
Treating friendships like a business that seeks to increase the return on investment without taking too many risks is symptomatic of Machiavellianism. These types of bonds are centered around self-interest and personal gain, hence the score-keeping. Research shows that Machiavellianism decreases the overall health of friendship. Additionally, women with these types of relationships frequently employed emotional manipulation towards their same-sex friends. And to no surprise, they believe their friends emotionally manipulate them as well. Trust and reciprocity are key features of healthy friendships. However, when interactions begin to feel disingenuous or opportunistic, as if you are strategizing, social climbing or being manipulated, it may be time to reconsider the actual benefits of this bond.
- Are you friends simply because they’re like you?
A common myth is that the best friendships are those that consist of people who share similarities based on race, socioeconomic status, upbringing, and so on. On the contrary, sameness within group bonds prevents the development of trust towards society and humanity at large. Basing your friendship on the fact that you went to the same high school or you both earn six-figure salaries, may be hindering your growth, happiness, and fullness as a human being. It can also subject you to burning through shallow connections that will ultimately always feel slightly lukewarm and tainted.
Scientific data proves that a higher frequency of contacts, a higher number of friends, and diversity within the friendship network are related to more social trust, less stress, and better health. What’s more, research has found that friendships do not develop by ignoring or downplaying differences between friends but rather they are more likely to be fulfilling when friends do not place a high value on similarity. While shared experiences and agreeable values can strengthen bonds, maintaining a relationship out of fear of otherness can be a symptom of low self-esteem or worse xenophobia. When we solely ground relationships in sameness, it hides us from the world, it denigrates the “outsiders”, and amplifies the “insiders”. In other words, is your friendship grounded by this sort of social convenience?
- Do you feel emotionally safe to be your full self?
Consider the ways you respond to and encourage vulnerability within friendships. Some may be reluctant to share and expose themselves out of fear of feeling shamed or diminished. Others may express vulnerability well but struggle with expressing themselves as emotionally safe. Close friendships are characterized by frequent interaction and affection, are less dependent upon proximity, and encourage moral accountability by way of garnering out deep attention to —friendship, vulnerability, and forgiveness.
Having the space to celebrate human connection, intimacy, and emotional truthfulness is the ultimate benefit of friendship. When there is a lack of opportunity to express our authentic selves without judgment, when we go on in our relationships without being truly acknowledged, nurtured, or understood, that is a symptom of an unhealthy, and perhaps violent, connection. The School of Life, eloquently demonstrated the power of vulnerability when they wrote:
“We can only get close by revealing things that would, in the wrong hands, be capable of inflicting appalling humiliation on us. Friendship is the dividend of gratitude that flows from an acknowledgment that one has offered something very valuable to someone: not a fancy present, but something even more precious, the key to one’s self-esteem and dignity.”
Friendship Breakup Can Be Necessary
Relishing in our vulnerabilities is the goal. However, if you walk away from interactions feeling small, mocked, or rejected when you reveal your full self or parts thereof, it is a strong indication that the relationship is not emotionally safe.
Asking ourselves the hard questions builds our capacity to be self-aware and self-actualizing adults. Most people want fulfilling, sincere relationships that allow them the latitude to grow and change. Those intense relationships undoubtedly take mutual commitment. There are also times where asking the hard questions reveals that we are in an unhealthy friendship; one that is based on utility, shallow sameness, or lack of emotional intimacy.
Taking the steps to discern whether a friendship is worth saving doesn’t happen overnight. These bonds are delicate, and the intricacies should be examined sans ego if possible. But if you’re like me, and you find yourself feeling a harrowing void because you know the time has come to let it go, rest assured that it is going to be okay. A friendship breakup is powerfully painful, and you will mourn the relationship just like any other. It’s important to recall those tender memories, celebrate the growth you’ve both experienced, and gracefully allow that bond to transition into a fond memory.
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Auri Whitaker
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